<?xml version="1.0" encoding="UTF-8"?><rss xmlns:dc="http://purl.org/dc/elements/1.1/" xmlns:content="http://purl.org/rss/1.0/modules/content/" xmlns:atom="http://www.w3.org/2005/Atom" version="2.0" xmlns:itunes="http://www.itunes.com/dtds/podcast-1.0.dtd" xmlns:googleplay="http://www.google.com/schemas/play-podcasts/1.0"><channel><title><![CDATA[The Diary of a Playboy]]></title><description><![CDATA[Stories, reflections, and difficult conversations about love, heartbreak, healing, desire, and what it means to be human.]]></description><link>https://thediaryofaplayboy.substack.com</link><image><url>https://substackcdn.com/image/fetch/$s_!zJpi!,w_256,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F3bc0642f-a38f-4158-a45e-047c9a73c998_1024x1024.png</url><title>The Diary of a Playboy</title><link>https://thediaryofaplayboy.substack.com</link></image><generator>Substack</generator><lastBuildDate>Wed, 04 Nov 2026 14:59:43 GMT</lastBuildDate><atom:link href="iframe.php?url=https%3A%2F%2Fthediaryofaplayboy.substack.com%2Ffeed" rel="self" type="application/rss+xml"/><copyright><![CDATA[Martins Itua]]></copyright><language><![CDATA[en]]></language><webMaster><![CDATA[thediaryofaplayboy@substack.com]]></webMaster><itunes:owner><itunes:email><![CDATA[thediaryofaplayboy@substack.com]]></itunes:email><itunes:name><![CDATA[Martins Itua]]></itunes:name></itunes:owner><itunes:author><![CDATA[Martins Itua]]></itunes:author><googleplay:owner><![CDATA[thediaryofaplayboy@substack.com]]></googleplay:owner><googleplay:email><![CDATA[thediaryofaplayboy@substack.com]]></googleplay:email><googleplay:author><![CDATA[Martins Itua]]></googleplay:author><itunes:block><![CDATA[Yes]]></itunes:block><item><title><![CDATA[The Morning After Breakup]]></title><description><![CDATA[The Scent of Someone Who Is No Longer Yours]]></description><link>https://thediaryofaplayboy.substack.com/p/the-morning-after-breakup</link><guid isPermaLink="false">https://thediaryofaplayboy.substack.com/p/the-morning-after-breakup</guid><dc:creator><![CDATA[Martins Itua]]></dc:creator><pubDate>Sun, 01 Nov 2026 21:35:52 GMT</pubDate><enclosure url="iframe.php?url=https%3A%2F%2Fsubstackcdn.com%2Fimage%2Ffetch%2F%24s_%21SxEs%21%2Cf_auto%2Cq_auto%3Agood%2Cfl_progressive%3Asteep%2Fhttps%253A%252F%252Fsubstack-post-media.s3.amazonaws.com%252Fpublic%252Fimages%252Fcaa1db47-55e1-4d6c-bccc-3d604b92ba9e_1099x1431.png" length="0" type="image/jpeg"/><content:encoded><![CDATA[<p>The cruelest thing about the morning after a breakup is that, for a few precious seconds, you forget.</p><p>You wake up as you always have. Perhaps you reach across the bed, expecting the familiar warmth of another body. Perhaps your hand instinctively searches for your phone, anticipating a message that has become as much a part of your morning as brushing your teeth. And then, without warning, yesterday returns.</p><div class="subscription-widget-wrap-editor" data-attrs="{&quot;url&quot;:&quot;https://thediaryofaplayboy.substack.com/subscribe?&quot;,&quot;text&quot;:&quot;Subscribe&quot;,&quot;language&quot;:&quot;en&quot;}" data-component-name="SubscribeWidgetToDOM"><div class="subscription-widget show-subscribe"><div class="preamble"><p class="cta-caption">The Diary of a Playboy is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.</p></div><form class="subscription-widget-subscribe"><input type="email" class="email-input" name="email" placeholder="Type your email&#8230;" tabindex="-1"><input type="submit" class="button primary" value="Subscribe"><div class="fake-input-wrapper"><div class="fake-input"></div><div class="fake-button"></div></div></form></div></div><p>It&#8217;s over.</p><p>You lie there, staring at the ceiling, trying to reconcile two realities. The one in which this person was part of your life just yesterday, and the one in which you must now learn to live without them.</p><p>But something strange happens. Their scent is still on the pillow. Their toothbrush is still in the bathroom. That ridiculous little thing they always did, the one that sometimes irritated you beyond reason, suddenly seems unbearably precious.</p><p>And you begin to wonder whether you have made a terrible mistake.</p><p>Or perhaps they made it for you.</p><p>There is something profoundly disorienting about losing someone who is still very much alive. They are somewhere in the same world, breathing the same air, perhaps waking up at precisely the same moment. You could call them. You know their number by heart. You know how they take their coffee, what makes them laugh, what frightens them in the middle of the night. Yet somehow, overnight, you have become strangers who know far too much about each other.</p><p>And nobody tells you what to do with all that knowledge.</p><p>The world, meanwhile, is spectacularly indifferent. The sun rises. Traffic builds. Someone sends a ridiculous message in the office WhatsApp group. Your neighbour starts their car. Life carries on with an almost offensive normality.</p><p>But inside you, something has shifted.</p><p>And perhaps the most unsettling part is that you cannot quite tell whether what you are feeling is heartbreak, loneliness, regret, wounded pride, or simply the terrifying absence of something that had become familiar.</p><p>Because sometimes, the person we miss most is the very person we knew we had to leave.</p><div class="captioned-image-container"><figure><a class="image-link image2 is-viewable-img" target="_blank" href="iframe.php?url=https%3A%2F%2Fsubstackcdn.com%2Fimage%2Ffetch%2F%24s_%21SxEs%21%2Cf_auto%2Cq_auto%3Agood%2Cfl_progressive%3Asteep%2Fhttps%253A%252F%252Fsubstack-post-media.s3.amazonaws.com%252Fpublic%252Fimages%252Fcaa1db47-55e1-4d6c-bccc-3d604b92ba9e_1099x1431.png" data-component-name="Image2ToDOM"><div class="image2-inset"><picture><source type="image/webp" srcset="https://substackcdn.com/image/fetch/$s_!SxEs!,w_424,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fcaa1db47-55e1-4d6c-bccc-3d604b92ba9e_1099x1431.png 424w, https://substackcdn.com/image/fetch/$s_!SxEs!,w_848,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fcaa1db47-55e1-4d6c-bccc-3d604b92ba9e_1099x1431.png 848w, https://substackcdn.com/image/fetch/$s_!SxEs!,w_1272,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fcaa1db47-55e1-4d6c-bccc-3d604b92ba9e_1099x1431.png 1272w, https://substackcdn.com/image/fetch/$s_!SxEs!,w_1456,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fcaa1db47-55e1-4d6c-bccc-3d604b92ba9e_1099x1431.png 1456w" sizes="auto, 100vw"><img src="iframe.php?url=https%3A%2F%2Fsubstackcdn.com%2Fimage%2Ffetch%2F%24s_%21SxEs%21%2Cw_1456%2Cc_limit%2Cf_auto%2Cq_auto%3Agood%2Cfl_progressive%3Asteep%2Fhttps%253A%252F%252Fsubstack-post-media.s3.amazonaws.com%252Fpublic%252Fimages%252Fcaa1db47-55e1-4d6c-bccc-3d604b92ba9e_1099x1431.png" width="1099" height="1431" data-attrs="{&quot;src&quot;:&quot;https://substack-post-media.s3.amazonaws.com/public/images/caa1db47-55e1-4d6c-bccc-3d604b92ba9e_1099x1431.png&quot;,&quot;srcNoWatermark&quot;:null,&quot;fullscreen&quot;:null,&quot;imageSize&quot;:null,&quot;height&quot;:1431,&quot;width&quot;:1099,&quot;resizeWidth&quot;:null,&quot;bytes&quot;:2071525,&quot;alt&quot;:null,&quot;title&quot;:null,&quot;type&quot;:&quot;image/png&quot;,&quot;href&quot;:null,&quot;belowTheFold&quot;:true,&quot;topImage&quot;:false,&quot;internalRedirect&quot;:&quot;https://thediaryofaplayboy.substack.com/i/223083412?img=https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fcaa1db47-55e1-4d6c-bccc-3d604b92ba9e_1099x1431.png&quot;,&quot;isProcessing&quot;:false,&quot;align&quot;:null,&quot;offset&quot;:false}" class="sizing-normal" alt="" srcset="https://substackcdn.com/image/fetch/$s_!SxEs!,w_424,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fcaa1db47-55e1-4d6c-bccc-3d604b92ba9e_1099x1431.png 424w, https://substackcdn.com/image/fetch/$s_!SxEs!,w_848,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fcaa1db47-55e1-4d6c-bccc-3d604b92ba9e_1099x1431.png 848w, https://substackcdn.com/image/fetch/$s_!SxEs!,w_1272,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fcaa1db47-55e1-4d6c-bccc-3d604b92ba9e_1099x1431.png 1272w, https://substackcdn.com/image/fetch/$s_!SxEs!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fcaa1db47-55e1-4d6c-bccc-3d604b92ba9e_1099x1431.png 1456w" sizes="auto, 100vw" loading="lazy"></picture><div class="image-link-expand"><div class="pencraft pc-display-flex pc-gap-8 pc-reset"><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container restack-image buttonBase-GK1x3M"><svg aria-hidden="true" width="20" height="20" viewBox="0 0 20 20" fill="none" stroke-width="1.5" stroke="var(--color-fg-primary)" stroke-linecap="round" stroke-linejoin="round" xmlns="http://www.w3.org/2000/svg" class="icon-noB79L"><g><path d="M2.53001 7.81595C3.49179 4.73911 6.43281 2.5 9.91173 2.5C13.1684 2.5 15.9537 4.46214 17.0852 7.23684L17.6179 8.67647M17.6179 8.67647L18.5002 4.26471M17.6179 8.67647L13.6473 6.91176M17.4995 12.1841C16.5378 15.2609 13.5967 17.5 10.1178 17.5C6.86118 17.5 4.07589 15.5379 2.94432 12.7632L2.41165 11.3235M2.41165 11.3235L1.5293 15.7353M2.41165 11.3235L6.38224 13.0882"></path></g></svg></button><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container view-image buttonBase-GK1x3M"><svg xmlns="http://www.w3.org/2000/svg" width="20" height="20" viewBox="0 0 24 24" fill="none" stroke="currentColor" stroke-width="2" stroke-linecap="round" stroke-linejoin="round" class="lucide lucide-maximize2 lucide-maximize-2 icon-noB79L"><polyline points="15 3 21 3 21 9"></polyline><polyline points="9 21 3 21 3 15"></polyline><line x1="21" x2="14" y1="3" y2="10"></line><line x1="3" x2="10" y1="21" y2="14"></line></svg></button></div></div></div></a></figure></div><p>And that is where heartbreak becomes complicated.</p><p>We like to imagine that the person who walks away has somehow escaped the pain. That the one who ends the relationship sleeps peacefully while the other lies awake, rehearsing conversations that can no longer change anything. But endings are rarely so conveniently divided between the wounded and the guilty.</p><p>Sometimes, the person who leaves cries harder than the person who was left. Sometimes, the one who begged for another chance wakes up feeling an unexpected sense of relief. And sometimes, two people spend their first morning apart secretly hoping the other will make the first call, even though neither has the slightest idea what they would say.</p><p>Pride is a remarkable companion to heartbreak. It can keep two people apart long after their anger has subsided. You stare at your phone, composing messages you never send. You wonder whether they are thinking about you. Whether they slept. Whether they have already told their friends. And, in one of heartbreak&#8217;s less dignified moments, whether they have had the audacity to eat breakfast.</p><p>But beneath these almost comical preoccupations lies a more difficult question.</p><p>What exactly are we grieving?</p><p>Is it the person? The love? The companionship? Or the version of ourselves that existed when we were together?</p><p>A relationship quietly reorganises our lives. We develop shared habits, private languages, familiar arguments and little rituals that would seem utterly meaningless to anyone else. We begin to imagine the future in the plural. Even our most ordinary decisions acquire another person&#8217;s presence.</p><p>And then, suddenly, we are expected to return to the singular.</p><p>Perhaps this explains why we sometimes miss relationships that were making us miserable. Familiarity has its own peculiar gravity. The mind can recognise that something was wrong while the heart continues to reach for what it knows.</p><p>Memory, unfortunately, is not always an impartial witness. In the silence following a breakup, it can become a rather enthusiastic editor, preserving the laughter while quietly removing the disappointments. The tenderness returns in vivid detail. The arguments become strangely difficult to recall. You remember how they held you, but conveniently forget how often you felt alone even in their presence.</p><p>And so begins that dangerous negotiation with yesterday.</p><p>What if I had been more patient? What if I had listened? What if we had tried one more time?</p><p>Of course, these questions are not always irrational. Some relationships end because of pride, impatience, misunderstanding or the inability of two otherwise compatible people to communicate. Regret can sometimes reveal genuine mistakes. There are apologies that should have been offered, conversations that should have happened and departures that might have been avoided.</p><p>But there are also relationships in which staying would have required the gradual abandonment of oneself. And missing someone does not necessarily mean leaving them was a mistake.</p><p>Perhaps the hardest part of the morning after is accepting that two apparently contradictory truths can coexist. You can love someone and know you cannot live with them. You can be relieved that a relationship has ended and still feel devastated by its absence. You can wish someone happiness while secretly dreading the day you discover they have found it without you.</p><p>And somewhere in all this confusion, life begins asking its ordinary questions again.</p><p>What will you have for breakfast? Are you going to work? Who will you call tonight?</p><p>For now, you have no answers to the larger questions. You do not know whether you will reconcile, whether you will fall in love again or whether this particular ache will ever become a distant memory.</p><p>You only know that morning has arrived.</p><p>And that faint scent on the pillow?</p><p>You hesitate before changing the sheets.</p><p>Not because you have decided to go back.</p><p>But because, for one more morning, you are not quite ready for the last trace of them to disappear.</p><p>Until next time,</p><p><strong>Martins</strong></p><p><em>If these words found a familiar place in your heart, perhaps you&#8217;ll feel at home here. Subscribe to The Diary of a Playboy for more reflections on love, desire, relationships and the beautiful contradictions of being human.</em></p><div class="subscription-widget-wrap-editor" data-attrs="{&quot;url&quot;:&quot;https://thediaryofaplayboy.substack.com/subscribe?&quot;,&quot;text&quot;:&quot;Subscribe&quot;,&quot;language&quot;:&quot;en&quot;}" data-component-name="SubscribeWidgetToDOM"><div class="subscription-widget show-subscribe"><div class="preamble"><p class="cta-caption">The Diary of a Playboy is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.</p></div><form class="subscription-widget-subscribe"><input type="email" class="email-input" name="email" placeholder="Type your email&#8230;" tabindex="-1"><input type="submit" class="button primary" value="Subscribe"><div class="fake-input-wrapper"><div class="fake-input"></div><div class="fake-button"></div></div></form></div></div>]]></content:encoded></item><item><title><![CDATA[ARE MARRIAGE AND HAPPINESS INCOMPATIBLE?]]></title><description><![CDATA[If Your Marriage Makes You Unhappy, Will Marrying Someone Else Make You Happy?]]></description><link>https://thediaryofaplayboy.substack.com/p/are-marriage-and-happiness-incompatible-0b0</link><guid isPermaLink="false">https://thediaryofaplayboy.substack.com/p/are-marriage-and-happiness-incompatible-0b0</guid><dc:creator><![CDATA[Martins Itua]]></dc:creator><pubDate>Sun, 18 Oct 2026 16:35:59 GMT</pubDate><enclosure url="iframe.php?url=https%3A%2F%2Fsubstackcdn.com%2Fimage%2Ffetch%2F%24s_%217zT0%21%2Cf_auto%2Cq_auto%3Agood%2Cfl_progressive%3Asteep%2Fhttps%253A%252F%252Fsubstack-post-media.s3.amazonaws.com%252Fpublic%252Fimages%252Fae601c7d-bf60-4af1-8624-8739b974e842_1536x1024.png" length="0" type="image/jpeg"/><content:encoded><![CDATA[<p>There is a question I have often wanted to ask people who tell me they are happily married.</p><p><strong>Are you really happy, or is that simply what you have learned to say?</strong></p><div class="subscription-widget-wrap-editor" data-attrs="{&quot;url&quot;:&quot;https://thediaryofaplayboy.substack.com/subscribe?&quot;,&quot;text&quot;:&quot;Subscribe&quot;,&quot;language&quot;:&quot;en&quot;}" data-component-name="SubscribeWidgetToDOM"><div class="subscription-widget show-subscribe"><div class="preamble"><p class="cta-caption">The Diary of a Playboy is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.</p></div><form class="subscription-widget-subscribe"><input type="email" class="email-input" name="email" placeholder="Type your email&#8230;" tabindex="-1"><input type="submit" class="button primary" value="Subscribe"><div class="fake-input-wrapper"><div class="fake-input"></div><div class="fake-button"></div></div></form></div></div><p>I suspect the answers, if people were completely honest, would make for some very uncomfortable conversations.</p><p>Think about it.</p><p>We congratulate people for getting married. We celebrate their anniversaries. We admire couples who have remained together for thirty or forty years. We describe them as successful, devoted, exemplary.</p><p>But successful at what?</p><p>Staying married?</p><p>Or being happy?</p><p>Because the two are not necessarily the same thing.</p><p>A man can spend thirty years married to a woman he no longer loves. A woman can share a bed with a husband she has not desired in years. They can raise wonderful children, acquire properties, attend church together, host friends, smile for photographs and celebrate another wedding anniversary.</p><p>And everyone will call them a happily married couple.</p><p>Perhaps they will even call themselves one.</p><p>But what happens when the guests leave, the photographs are put away and the two people at the centre of the celebration return to a life neither particularly enjoys?</p><p><strong>At what point did we begin mistaking the longevity of a marriage for the happiness of the people inside it?</strong></p><p>And why are we so uncomfortable asking?</p><p>I have sometimes wondered whether marriage and happiness are not, in fact, an oxymoron. Two things we have been conditioned to associate with each other, even though one does not necessarily produce the other.</p><p>Consider the extraordinary expectations we attach to marriage.</p><p>We tell young people to find someone who makes them happy. We encourage them to marry for love. We assure them that finding the right person will change their lives. We speak of marriage as though it were the final destination of an emotional journey, the place where loneliness ends, fulfilment begins and happiness finally finds a permanent address.</p><p>Then, almost immediately after the wedding, we begin telling them something quite different.</p><p>Marriage is hard.</p><p>Marriage requires sacrifice.</p><p>Marriage is not always about happiness.</p><p>You must endure.</p><p>You must compromise.</p><p>You must learn to live with disappointment.</p><p>And if things become unbearable, someone will inevitably remind you that you made a vow.</p><p>I find that contradiction fascinating.</p><p><strong>Before marriage, we sell people happiness. After marriage, we teach them endurance.</strong></p><p>And somehow, we expect them not to notice the difference.</p><p>But perhaps the problem begins even earlier.</p><p>Perhaps we have been asking the wrong question all along.</p><p>Why do people get married?</p><p>Not why they say they get married. Not the beautifully rehearsed answers they give at engagement parties or during marriage counselling.</p><p>I mean the real reasons.</p><p>Some marry for love. Others for money. Some want children. Some want financial security. Others want social acceptance, companionship, respectability or the reassurance that they will not grow old alone.</p><p>Some marry because their parents expect it. Some because their friends are getting married. Some because their religion encourages it. Some because they are tired of being asked when they will settle down.</p><p>And some, believe it or not, marry because they want to have sex.</p><p>I remember a conversation with my driver some years ago.</p><p>He told me he wanted to get married.</p><p>I asked him why.</p><p>He smiled and quoted the Bible.</p><p>&#8220;It&#8217;s better to marry than to burn.&#8221;</p><p>I looked at him.</p><p>&#8220;So you want to get married just to have sex?&#8221;</p><p>&#8220;Yes,&#8221; he replied.</p><p>I laughed.</p><p>And said nothing more.</p><p>But I have thought about that conversation since.</p><p>Here was a man who, perhaps without realising it, had exposed something profoundly important about marriage.</p><p>He had identified what he wanted.</p><p>Not necessarily love. Not necessarily companionship. Not necessarily the emotional and intellectual partnership we so often associate with marriage.</p><p>He wanted sex, within the boundaries of his religious convictions.</p><p>And he was perfectly honest about it.</p><p>But what happens when someone enters marriage for one particular reason and discovers that marriage cannot guarantee the very thing they came looking for?</p><p>What happens when a woman marries for financial security and eventually discovers that money cannot compensate for emotional loneliness?</p><p>What happens when a man marries because he wants children, has those children, and then discovers that he has very little in common with the woman raising them?</p><p>What happens when two people marry for love and wake up fifteen years later wondering where that love went?</p><p>And perhaps most troubling of all, <strong>what happens when your marriage gives you everything you thought you wanted, and you are still unhappy?</strong></p><p>Do you stay?</p><p>Do you leave?</p><p>Do you find someone else?</p><p>And if you marry someone else, what guarantees that happiness will be waiting for you there?</p><p>I have been thinking about these questions for some time. I first explored them in January, but the more I reflected on the subject, the more I realised that I had barely scratched the surface.</p><p>Because beneath our beautiful wedding ceremonies, our religious convictions, our social expectations and our declarations of marital bliss lies a question we seem determined not to confront.</p><p><strong>What if marriage was never designed to make us happy, and we have spent generations blaming our spouses for failing to deliver a promise the institution itself never made?</strong></p><p>But then another question immediately follows.</p><p><strong>If marriage is not supposed to make us happy, why should anyone willingly spend the rest of their life in one that makes them miserable?</strong></p><p>That is where this conversation begins.</p><div class="captioned-image-container"><figure><a class="image-link image2 is-viewable-img" target="_blank" href="iframe.php?url=https%3A%2F%2Fsubstackcdn.com%2Fimage%2Ffetch%2F%24s_%217zT0%21%2Cf_auto%2Cq_auto%3Agood%2Cfl_progressive%3Asteep%2Fhttps%253A%252F%252Fsubstack-post-media.s3.amazonaws.com%252Fpublic%252Fimages%252Fae601c7d-bf60-4af1-8624-8739b974e842_1536x1024.png" data-component-name="Image2ToDOM"><div class="image2-inset"><picture><source type="image/webp" srcset="https://substackcdn.com/image/fetch/$s_!7zT0!,w_424,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fae601c7d-bf60-4af1-8624-8739b974e842_1536x1024.png 424w, https://substackcdn.com/image/fetch/$s_!7zT0!,w_848,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fae601c7d-bf60-4af1-8624-8739b974e842_1536x1024.png 848w, https://substackcdn.com/image/fetch/$s_!7zT0!,w_1272,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fae601c7d-bf60-4af1-8624-8739b974e842_1536x1024.png 1272w, https://substackcdn.com/image/fetch/$s_!7zT0!,w_1456,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fae601c7d-bf60-4af1-8624-8739b974e842_1536x1024.png 1456w" sizes="auto, 100vw"><img src="iframe.php?url=https%3A%2F%2Fsubstackcdn.com%2Fimage%2Ffetch%2F%24s_%217zT0%21%2Cw_1456%2Cc_limit%2Cf_auto%2Cq_auto%3Agood%2Cfl_progressive%3Asteep%2Fhttps%253A%252F%252Fsubstack-post-media.s3.amazonaws.com%252Fpublic%252Fimages%252Fae601c7d-bf60-4af1-8624-8739b974e842_1536x1024.png" width="1456" height="971" 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class="image-link-expand"><div class="pencraft pc-display-flex pc-gap-8 pc-reset"><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container restack-image buttonBase-GK1x3M"><svg aria-hidden="true" width="20" height="20" viewBox="0 0 20 20" fill="none" stroke-width="1.5" stroke="var(--color-fg-primary)" stroke-linecap="round" stroke-linejoin="round" xmlns="http://www.w3.org/2000/svg" class="icon-noB79L"><g><path d="M2.53001 7.81595C3.49179 4.73911 6.43281 2.5 9.91173 2.5C13.1684 2.5 15.9537 4.46214 17.0852 7.23684L17.6179 8.67647M17.6179 8.67647L18.5002 4.26471M17.6179 8.67647L13.6473 6.91176M17.4995 12.1841C16.5378 15.2609 13.5967 17.5 10.1178 17.5C6.86118 17.5 4.07589 15.5379 2.94432 12.7632L2.41165 11.3235M2.41165 11.3235L1.5293 15.7353M2.41165 11.3235L6.38224 13.0882"></path></g></svg></button><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container view-image buttonBase-GK1x3M"><svg xmlns="http://www.w3.org/2000/svg" width="20" height="20" viewBox="0 0 24 24" fill="none" stroke="currentColor" stroke-width="2" stroke-linecap="round" stroke-linejoin="round" class="lucide lucide-maximize2 lucide-maximize-2 icon-noB79L"><polyline points="15 3 21 3 21 9"></polyline><polyline points="9 21 3 21 3 15"></polyline><line x1="21" x2="14" y1="3" y2="10"></line><line x1="3" x2="10" y1="21" y2="14"></line></svg></button></div></div></div></a></figure></div><p>Consider a woman who has been married for twenty-three years.</p><p>Her husband is a decent man. He provides for his family, loves his children, pays the bills and has never raised a hand against her. He is not having an affair. He does not gamble away their money or disappear for days without explanation.</p><p>By almost every conventional measure, she has a good husband.</p><p>Yet she is unhappy.</p><p>Not occasionally unhappy. Not simply going through a difficult season. She has been unhappy for so long that she can scarcely remember what it felt like to look forward to being alone with him.</p><p>Their conversations revolve around bills, children, family obligations and the practical arrangements of everyday life. They rarely quarrel. There is hardly anything left to quarrel about. She has stopped expecting him to understand her, and he has stopped noticing that she no longer tries.</p><p>He thinks they have a good marriage.</p><p>She thinks she has lost twenty-three years of her life.</p><p>Now tell me, who is wrong?</p><p>What exactly is she supposed to complain about? That her husband is responsible? That he has remained faithful? That he comes home every evening?</p><p>How does she explain to her family that she wants to leave a man everyone considers a blessing?</p><p>And what does she say to him?</p><p>&#8220;You have done nothing terrible. I simply do not want to spend the rest of my life with you.&#8221;</p><p>Imagine being the person on the receiving end of those words.</p><p>Imagine discovering that the marriage you have spent decades protecting has become a place from which your spouse desperately wants to escape.</p><p>We are comfortable discussing marriages destroyed by violence, infidelity or cruelty. Those situations give us identifiable wrongdoing and, sometimes, a clearer moral position. Abuse, in particular, is not something anyone should be expected to endure in the name of commitment.</p><p>But what do we do with a marriage in which nobody has committed an obvious offence?</p><p><strong>Can someone be a good spouse and still be the wrong person for you?</strong></p><p>And if the answer is yes, does being unhappy give you the right to leave someone who has kept every promise they made to you?</p><p>Perhaps the more difficult question is whether marriage gives one person a permanent claim on another person&#8217;s future simply because they once agreed to share it.</p><p>We speak of commitment as though the people making it will remain essentially unchanged. Yet the woman who married at twenty-five may have very different emotional, intellectual and personal needs at fifty. The man she married may have changed too. Or perhaps he has remained almost exactly the same, and that is part of the problem.</p><p>People grow. Sometimes together. Sometimes in opposite directions. Sometimes one grows while the other is perfectly content to remain where they have always been.</p><p>And here is something we rarely acknowledge.</p><p><strong>The fact that someone is satisfied with a marriage does not necessarily mean the marriage is satisfying to the other person.</strong></p><p>Two people can inhabit the same relationship and experience entirely different lives.</p><p>One sees stability. The other sees stagnation.</p><p>One feels secure. The other feels trapped.</p><p>One believes the absence of conflict is evidence of peace. The other knows it is evidence that they have stopped trying.</p><p>So whose experience determines whether the marriage is working?</p><p>We might say they should communicate. Seek counselling. Rediscover intimacy. Make time for each other.</p><p>Of course they should, where both are willing and there is something to rebuild.</p><p>But suppose they have done all that.</p><p>Suppose they have talked until there is nothing new to say. Suppose they have attended counselling, taken holidays, made promises, changed routines and sincerely attempted to recover what once existed.</p><p>And suppose nothing changes.</p><p>At what point does perseverance become an inability to accept reality?</p><p>Or is it possible that we sometimes declare a marriage beyond repair because we are unwilling to confront what repairing it would require of us?</p><p>Neither possibility is particularly comfortable.</p><p>Now introduce another person.</p><p>Not necessarily an affair. Perhaps a colleague, an old friend or someone encountered quite innocently.</p><p>Someone who listens.</p><p>Someone who asks questions and remembers the answers.</p><p>Someone who laughs at your jokes, notices when you are unusually quiet and seems genuinely interested in the person you have become.</p><p>Suddenly, something begins to stir.</p><p>You find yourself looking forward to conversations again. You feel attractive, interesting, understood. Parts of your personality that seemed to have disappeared begin to reappear.</p><p>And then comes the dangerous thought.</p><p><strong>Perhaps I married the wrong person.</strong></p><p>But did you?</p><p>Or have you simply encountered someone who is meeting needs your marriage has neglected for years?</p><p>There is a difference.</p><p>The new person has not yet disappointed you over unpaid bills. You have not argued about whose family to visit at Christmas. You have not spent sleepless nights nursing a sick child together or endured the exhausting familiarity of managing a household.</p><p>They know your stories, but they have not necessarily lived through the circumstances that produced them.</p><p>They see you at your most engaging. You see them at theirs.</p><p>And because neither of you has yet had to survive the ordinary demands of a shared life, the connection can appear almost effortless.</p><p><strong>It is remarkably easy to mistake the absence of shared problems for the presence of extraordinary compatibility.</strong></p><p>But we must be careful here.</p><p>Not every new relationship is an illusion. Sometimes meeting another person reveals how profoundly unfulfilled the previous relationship has become. Sometimes two people really are better suited to each other. Sometimes leaving creates the possibility of a healthier, more loving and more honest life.</p><p>The difficulty is knowing which experience you are having before making a decision that cannot easily be reversed.</p><p>Are you in love with this new person?</p><p>Or are you in love with how you feel about yourself when you are with them?</p><p>And if you eventually married them, would that feeling survive ten years of ordinary life?</p><p>This brings me to something I have often wondered about people who marry repeatedly.</p><p>One of my favourite actresses, Geena Davis, has been married four times. All four marriages ended in divorce.</p><p>I mention her not because I know what happened inside those relationships, or because the number of marriages someone has had tells us whether they are capable of love. It tells us neither.</p><p>But her marital history raises an interesting question about our enduring faith in the next beginning.</p><p>What makes someone believe, after one marriage has ended, that another will succeed?</p><p>Hope, perhaps.</p><p>Experience.</p><p>The conviction that they have finally found someone more compatible.</p><p>And why not? People can learn from their mistakes. They can mature. They can discover qualities they previously overlooked and build genuinely happier relationships.</p><p>But what happens when the second marriage ends?</p><p>Or the third?</p><p>At what point should we begin asking whether the problem lies exclusively with the people we have married?</p><p>Imagine moving from one marriage to another, convinced each time that happiness is waiting just beyond the next wedding ceremony.</p><p>The faces change. The homes change. The wedding photographs change.</p><p>But perhaps the same arguments eventually return.</p><p>The same disappointments.</p><p>The same feeling of being misunderstood.</p><p>The same suspicion that something better must exist elsewhere.</p><p><strong>What if the one person who has accompanied you into every unhappy marriage is the person you have never seriously examined?</strong></p><p>That question may sound accusatory, but it is not intended to be.</p><p>There are people who have endured genuinely destructive relationships through no fault of their own. There are also people whose later marriages are far happier than their earlier ones.</p><p>Yet self-examination remains important because leaving a relationship does not automatically mean we have understood why it failed.</p><p>We may divorce a controlling spouse and subsequently discover that we are drawn to controlling personalities.</p><p>We may leave someone emotionally unavailable and find ourselves pursuing another person who cannot offer intimacy.</p><p>We may complain that our partners never listen, without ever considering whether we know how to communicate our needs without criticism or resentment.</p><p>And sometimes we may discover that the unhappiness we attributed entirely to marriage was connected to dissatisfaction with our careers, our ageing, our unrealised ambitions or the lives we imagined we would be living by now.</p><p>A spouse can become a convenient explanation for disappointments that extend far beyond the relationship.</p><p>But the reverse is equally true.</p><p>People can spend years working on themselves, becoming more patient, more emotionally mature and more understanding, only to discover that their marriage remains deeply unfulfilling.</p><p><strong>Personal growth does not guarantee marital compatibility.</strong></p><p>And recognising your own shortcomings does not oblige you to remain indefinitely in a relationship that cannot meet your legitimate emotional needs.</p><p>So where does that leave us?</p><p>Perhaps with an even more uncomfortable reality.</p><p>Marriage is not simply a relationship between two people. It often becomes an entire network of obligations involving children, parents, property, finances, religion, friendships and social identity.</p><p>When a marriage ends, the consequences rarely stop with the couple.</p><p>Consider the children.</p><p>We often hear that parents should remain together for their sake.</p><p>There is something understandable about that argument. Children benefit from stability, dependable care and the reassurance that the people responsible for them will continue to provide a secure environment.</p><p>But what kind of stability are we describing?</p><p>A household where two parents barely speak?</p><p>A home where affection has disappeared and resentment quietly governs everyday interactions?</p><p>A family in which children grow up believing that marriage means tolerating emotional emptiness because leaving would be considered selfish?</p><p>Children learn about relationships not only from what their parents tell them, but also from what they observe.</p><p>Yet divorce does not automatically improve their lives either.</p><p>Separation can mean disrupted routines, financial pressure, divided households, painful loyalties and the loss of everyday contact with a parent. Some children experience relief when conflict ends. Others experience profound distress even when their parents believe the separation was necessary.</p><p>And many experience both.</p><p>So the question is not simply whether children are better off with married or divorced parents.</p><p>It is what kind of life the adults are creating for them, and whether that life can be improved within the marriage or outside it.</p><p>But even that leaves a troubling moral dilemma.</p><p><strong>How much of their own happiness should parents be expected to sacrifice for their children?</strong></p><p>Five years?</p><p>Ten?</p><p>Until the youngest turns eighteen?</p><p>And when the children finally leave home, what happens to the two people who have spent decades postponing a decision neither wanted to make?</p><p>Do they rediscover each other?</p><p>Or do they look across the dinner table and realise that the children were the last remaining conversation between them?</p><p>There is no answer that leaves everyone untouched.</p><p>And perhaps that is why so many people stay.</p><p>Not because they are happy.</p><p>Not because they believe the marriage can recover.</p><p>But because every available alternative seems to demand a price they are unwilling or unable to pay.</p><p>Financial dependence can make leaving almost impossible. Religious convictions can make divorce morally unthinkable. Family expectations can turn a private decision into a public confrontation. The fear of loneliness can make an unhappy marriage seem preferable to an uncertain future.</p><p>And sometimes, after years of disappointment, people simply become accustomed to the lives they have.</p><p>There is a peculiar comfort in familiar unhappiness.</p><p>You know what to expect. You know which conversations to avoid. You know how to organise your days so that the things missing from your marriage become less noticeable.</p><p>You learn to find fulfilment elsewhere.</p><p>In work.</p><p>In friendships.</p><p>In children.</p><p>In faith.</p><p>In private interests your spouse does not share.</p><p>You stop expecting marriage to provide everything.</p><p>And perhaps, for some people, that is not resignation at all. Perhaps it is a mature accommodation between two adults who understand that no single relationship can satisfy every human need.</p><p>But for others, it is something much sadder.</p><p>They have not made peace with their marriage.</p><p>They have made peace with never being happy in it.</p><p>How do we tell the difference?</p><p>And who are we to tell someone that the life they have accepted is not good enough?</p><p>This is where the modern language of personal happiness becomes particularly complicated.</p><p>We tell people they have only one life to live.</p><p>That they deserve joy.</p><p>That they should never settle.</p><p>That they must choose themselves.</p><p>There is wisdom in some of that advice. Nobody should be expected to surrender their dignity, safety or entire sense of self merely to preserve the appearance of marriage.</p><p>But does the pursuit of happiness have no obligations?</p><p>What happens when choosing yourself means devastating someone who has built their future around you?</p><p>What happens when your freedom becomes another person&#8217;s grief?</p><p>And what happens when the happiness you are pursuing turns out to be temporary?</p><p>We cannot demand that people remain miserable simply because leaving will hurt others. But neither can we pretend that our personal happiness exists independently of the lives intertwined with ours.</p><p>Perhaps this is why marriage is so difficult to discuss honestly.</p><p>It brings competing truths into the same room.</p><p>A person may have a legitimate reason to leave, while their spouse has a legitimate reason to feel betrayed by that decision.</p><p>A marriage may have been meaningful for twenty years and still need to end.</p><p>A divorce may be necessary and still produce regret.</p><p>A person may remain married out of love, or out of fear, or out of a mixture of both that even they cannot fully explain.</p><p>And someone who leaves an unhappy marriage may discover that being unmarried does not automatically make them happy.</p><p>We are dealing with human lives, not mathematical equations.</p><p>But there is one more contradiction I find difficult to ignore.</p><p>We spend an extraordinary amount of time encouraging people to get married, yet remarkably little time asking whether they actually want the life marriage requires.</p><p>A young woman announces her engagement, and everyone celebrates.</p><p>A young man says he is getting married, and people congratulate him on becoming responsible.</p><p>But imagine asking either of them a few uncomfortable questions.</p><p>Would you still marry this person if you knew the sexual excitement might diminish?</p><p>Would you still marry if children never came?</p><p>Would you still marry if your spouse became seriously ill and required years of care?</p><p>Would you still marry if financial prosperity never arrived?</p><p>Would you still choose this person if they remained essentially who they are today, rather than becoming the person you hope they will eventually be?</p><p>And perhaps the most revealing question of all:</p><p><strong>If marriage did not promise to make you happy, would you still want to get married?</strong></p><p>I wonder how many engagements would survive an entirely honest conversation about those questions.</p><p>Not because people do not love each other.</p><p>But because love and readiness for marriage are not necessarily the same thing.</p><p>We may love someone deeply and still be unwilling to live the life that loving them within marriage will require.</p><p>We may desire the wedding without understanding the commitment.</p><p>We may want children without wanting the demands of partnership.</p><p>We may want companionship without accepting that another human being will sometimes disappoint us.</p><p>And we may want happiness without having any clear understanding of what happiness actually means.</p><p>Perhaps that is the question we should have been asking long before the wedding invitations were printed.</p><p>Not simply whether we love each other.</p><p>But whether we understand what we are choosing, why we are choosing it, and what we will do when the life we eventually experience looks nothing like the one we imagined.</p><h2>THE QUESTION THAT REMAINS</h2><p>I wonder what would happen if we stopped asking married people whether they were happily married.</p><p>And asked them something else instead.</p><p><strong>Knowing everything you know today, would you marry the same person again?</strong></p><p>Not the person you met twenty years ago.</p><p>Not the person you imagined they would become.</p><p>The person you know now, with all their virtues, disappointments, contradictions and imperfections.</p><p>Would you still choose them?</p><p>I suspect that question would produce some extraordinary conversations.</p><p>Some people would say yes without hesitation. Others would need time to think. Some might discover that they love their spouses deeply but would not willingly repeat the life they have shared.</p><p>And perhaps a few would confront a truth they have spent years avoiding.</p><p>That they are not necessarily unhappy with the person they married.</p><p>They are unhappy with the life they have lived.</p><p>There is a difference.</p><p>But there is another possibility.</p><p>What if you would marry the same person again, knowing that the marriage would contain disappointment, sacrifice, periods of loneliness and moments when happiness seemed very far away?</p><p>Would that make your marriage successful?</p><p>Or would it simply mean that, despite everything, you believe the life you built together was worth the price?</p><p>Perhaps we have been too quick to demand that marriage justify itself through happiness alone.</p><p>A marriage can give people children they adore, memories they treasure, security they value and companionship that becomes more meaningful with age. It can also contain profound sadness.</p><p>Does the sadness invalidate everything else?</p><p>And does everything else justify the sadness?</p><p>I do not know that anyone can answer those questions for another person.</p><p>But I am increasingly convinced that one of the greatest mistakes we make is allowing society to answer them for us.</p><p>Society celebrates the wedding but does not live the marriage.</p><p>It applauds the anniversary but does not share the bedroom.</p><p>It praises endurance but rarely asks what is being endured.</p><p>And when a marriage ends, it is often the people who know the least about what happened inside it who have the strongest opinions.</p><p>Perhaps that is why we need to become more honest about marriage.</p><p>Not because marriage is a bad institution. Not because divorce is necessarily liberation. And certainly not because happiness is unimportant.</p><p>But because marriage is too consequential a decision to be built on assumptions we are afraid to examine.</p><p>We should be able to acknowledge that some people are genuinely happy in marriage without pretending that everyone else must be.</p><p>We should be able to recognise that some marriages deserve another chance without insisting that every marriage must survive.</p><p>We should be able to celebrate people who remain together without condemning those who discover that they cannot.</p><p>And perhaps we should stop treating the decision to marry as an achievement in itself.</p><p><strong>Getting married is an event. Remaining married is a circumstance. Neither, on its own, tells us whether two people have lived well together.</strong></p><p>I began this conversation by asking whether marriage and happiness are incompatible.</p><p>I am not certain that is even the right question anymore.</p><p>Because perhaps marriage was never meant to guarantee happiness. Perhaps it offers the possibility of building a shared life, with all the beauty, responsibility, disappointment and uncertainty that such a life entails.</p><p>But possibility is not a promise.</p><p>And commitment is not a guarantee.</p><p>The person you marry may become your greatest source of joy. They may become your deepest disappointment. Sometimes, painfully, they may become both.</p><p>You may leave and discover a happiness you never thought possible.</p><p>You may leave and discover that some of the unhappiness you were running from has followed you.</p><p>You may stay and rebuild something beautiful.</p><p>Or you may stay and spend the rest of your life wondering what might have happened if you had found the courage to leave.</p><p>There are no easy answers because there are no consequences-free choices.</p><p>But perhaps there is one question worth asking before we decide that another marriage, another partner or another life will finally make us happy.</p><p><strong>If you cannot explain what happiness means to you, how will you recognise it when you find it?</strong></p><p>And if you do find it, how will you know whether it came from the person beside you or from something that finally changed within yourself?</p><p>I would genuinely like to hear what you think.</p><p>If you are married, are you happy? And if you are, what does that happiness actually consist of?</p><p>If you are unhappy, do you believe marrying someone else would change that?</p><p>And if you have been married more than once, what did the experience teach you about the difference between finding the right person and becoming the right person?</p><p>These are not questions I ask to judge anyone. I ask because I suspect that behind many of our confident declarations about marriage are experiences we have never quite found the courage to discuss.</p><p>Perhaps it is time we did.</p><p>If this conversation challenged something you have always believed about marriage, consider becoming a paid subscriber to <em>The Diary of a Playboy</em>. Your support helps me continue exploring the questions we often avoid and the uncomfortable truths that deserve a closer look.</p><p>To everyone who reads, shares, comments and returns, thank you. You are the reason these conversations continue.</p><p>Until next time, remember that a wedding may begin a marriage, but it cannot promise the life that follows.</p><p>And perhaps the saddest thing is not discovering that marriage did not make you happy.</p><p><strong>It is spending a lifetime pretending that it did.</strong></p><p><em>Martins Itua</em></p><div class="subscription-widget-wrap-editor" data-attrs="{&quot;url&quot;:&quot;https://thediaryofaplayboy.substack.com/subscribe?&quot;,&quot;text&quot;:&quot;Subscribe&quot;,&quot;language&quot;:&quot;en&quot;}" data-component-name="SubscribeWidgetToDOM"><div class="subscription-widget show-subscribe"><div class="preamble"><p class="cta-caption">The Diary of a Playboy is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.</p></div><form class="subscription-widget-subscribe"><input type="email" class="email-input" name="email" placeholder="Type your email&#8230;" tabindex="-1"><input type="submit" class="button primary" value="Subscribe"><div class="fake-input-wrapper"><div class="fake-input"></div><div class="fake-button"></div></div></form></div></div>]]></content:encoded></item><item><title><![CDATA[SHOULD SHE TELL HIM?]]></title><description><![CDATA[What Happens After the Guilt]]></description><link>https://thediaryofaplayboy.substack.com/p/should-she-tell-him</link><guid isPermaLink="false">https://thediaryofaplayboy.substack.com/p/should-she-tell-him</guid><dc:creator><![CDATA[Martins Itua]]></dc:creator><pubDate>Fri, 25 Sep 2026 17:46:30 GMT</pubDate><enclosure url="iframe.php?url=https%3A%2F%2Fsubstackcdn.com%2Fimage%2Ffetch%2F%24s_%21UO1X%21%2Cf_auto%2Cq_auto%3Agood%2Cfl_progressive%3Asteep%2Fhttps%253A%252F%252Fsubstack-post-media.s3.amazonaws.com%252Fpublic%252Fimages%252F6a7e7a19-1db9-40ea-8df3-44429332c8ec_1099x1431.png" length="0" type="image/jpeg"/><content:encoded><![CDATA[<h3><strong><span data-color="#ff0000" style="color: rgb(255, 0, 0);">BEFORE YOU READ...</span></strong></h3><p>In Part One, we explored the woman who cheated, went home, and continued living beside a husband who never found out.</p><p>But guilt eventually asks for an answer.</p><div class="subscription-widget-wrap-editor" data-attrs="{&quot;url&quot;:&quot;https://thediaryofaplayboy.substack.com/subscribe?&quot;,&quot;text&quot;:&quot;Subscribe&quot;,&quot;language&quot;:&quot;en&quot;}" data-component-name="SubscribeWidgetToDOM"><div class="subscription-widget show-subscribe"><div class="preamble"><p class="cta-caption">The Diary of a Playboy is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.</p></div><form class="subscription-widget-subscribe"><input type="email" class="email-input" name="email" placeholder="Type your email&#8230;" tabindex="-1"><input type="submit" class="button primary" value="Subscribe"><div class="fake-input-wrapper"><div class="fake-input"></div><div class="fake-button"></div></div></form></div></div><p><strong>Should she tell him?</strong></p><p>Would confession be an act of honesty?</p><p>Or would she simply be relieving herself of a burden by handing the pain to him?</p><p>That is where we begin.</p><div class="captioned-image-container"><figure><a class="image-link image2 is-viewable-img" target="_blank" href="iframe.php?url=https%3A%2F%2Fsubstackcdn.com%2Fimage%2Ffetch%2F%24s_%21UO1X%21%2Cf_auto%2Cq_auto%3Agood%2Cfl_progressive%3Asteep%2Fhttps%253A%252F%252Fsubstack-post-media.s3.amazonaws.com%252Fpublic%252Fimages%252F6a7e7a19-1db9-40ea-8df3-44429332c8ec_1099x1431.png" data-component-name="Image2ToDOM"><div class="image2-inset"><picture><source type="image/webp" srcset="https://substackcdn.com/image/fetch/$s_!UO1X!,w_424,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F6a7e7a19-1db9-40ea-8df3-44429332c8ec_1099x1431.png 424w, https://substackcdn.com/image/fetch/$s_!UO1X!,w_848,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F6a7e7a19-1db9-40ea-8df3-44429332c8ec_1099x1431.png 848w, https://substackcdn.com/image/fetch/$s_!UO1X!,w_1272,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F6a7e7a19-1db9-40ea-8df3-44429332c8ec_1099x1431.png 1272w, https://substackcdn.com/image/fetch/$s_!UO1X!,w_1456,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F6a7e7a19-1db9-40ea-8df3-44429332c8ec_1099x1431.png 1456w" sizes="100vw"><img src="iframe.php?url=https%3A%2F%2Fsubstackcdn.com%2Fimage%2Ffetch%2F%24s_%21UO1X%21%2Cw_1456%2Cc_limit%2Cf_auto%2Cq_auto%3Agood%2Cfl_progressive%3Asteep%2Fhttps%253A%252F%252Fsubstack-post-media.s3.amazonaws.com%252Fpublic%252Fimages%252F6a7e7a19-1db9-40ea-8df3-44429332c8ec_1099x1431.png" width="1099" height="1431" data-attrs="{&quot;src&quot;:&quot;https://substack-post-media.s3.amazonaws.com/public/images/6a7e7a19-1db9-40ea-8df3-44429332c8ec_1099x1431.png&quot;,&quot;srcNoWatermark&quot;:null,&quot;fullscreen&quot;:null,&quot;imageSize&quot;:null,&quot;height&quot;:1431,&quot;width&quot;:1099,&quot;resizeWidth&quot;:null,&quot;bytes&quot;:1812755,&quot;alt&quot;:null,&quot;title&quot;:null,&quot;type&quot;:&quot;image/png&quot;,&quot;href&quot;:null,&quot;belowTheFold&quot;:false,&quot;topImage&quot;:true,&quot;internalRedirect&quot;:&quot;https://thediaryofaplayboy.substack.com/i/217428485?img=https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F6a7e7a19-1db9-40ea-8df3-44429332c8ec_1099x1431.png&quot;,&quot;isProcessing&quot;:false,&quot;align&quot;:null,&quot;offset&quot;:false}" class="sizing-normal" alt="" srcset="https://substackcdn.com/image/fetch/$s_!UO1X!,w_424,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F6a7e7a19-1db9-40ea-8df3-44429332c8ec_1099x1431.png 424w, https://substackcdn.com/image/fetch/$s_!UO1X!,w_848,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F6a7e7a19-1db9-40ea-8df3-44429332c8ec_1099x1431.png 848w, https://substackcdn.com/image/fetch/$s_!UO1X!,w_1272,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F6a7e7a19-1db9-40ea-8df3-44429332c8ec_1099x1431.png 1272w, https://substackcdn.com/image/fetch/$s_!UO1X!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F6a7e7a19-1db9-40ea-8df3-44429332c8ec_1099x1431.png 1456w" sizes="100vw" fetchpriority="high"></picture><div class="image-link-expand"><div class="pencraft pc-display-flex pc-gap-8 pc-reset"><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container restack-image buttonBase-GK1x3M"><svg aria-hidden="true" width="20" height="20" viewBox="0 0 20 20" fill="none" stroke-width="1.5" stroke="var(--color-fg-primary)" stroke-linecap="round" stroke-linejoin="round" xmlns="http://www.w3.org/2000/svg" class="icon-noB79L"><g><path d="M2.53001 7.81595C3.49179 4.73911 6.43281 2.5 9.91173 2.5C13.1684 2.5 15.9537 4.46214 17.0852 7.23684L17.6179 8.67647M17.6179 8.67647L18.5002 4.26471M17.6179 8.67647L13.6473 6.91176M17.4995 12.1841C16.5378 15.2609 13.5967 17.5 10.1178 17.5C6.86118 17.5 4.07589 15.5379 2.94432 12.7632L2.41165 11.3235M2.41165 11.3235L1.5293 15.7353M2.41165 11.3235L6.38224 13.0882"></path></g></svg></button><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container view-image buttonBase-GK1x3M"><svg xmlns="http://www.w3.org/2000/svg" width="20" height="20" viewBox="0 0 24 24" fill="none" stroke="currentColor" stroke-width="2" stroke-linecap="round" stroke-linejoin="round" class="lucide lucide-maximize2 lucide-maximize-2 icon-noB79L"><polyline points="15 3 21 3 21 9"></polyline><polyline points="9 21 3 21 3 15"></polyline><line x1="21" x2="14" y1="3" y2="10"></line><line x1="3" x2="10" y1="21" y2="14"></line></svg></button></div></div></div></a></figure></div><p><strong>What if confessing is the selfish thing to do?</strong></p><p>You cheated.</p><p>Your husband doesn&#8217;t know.</p><p>You regret it deeply. It will never happen again.</p><p>Telling him may destroy your marriage, wound a man who did nothing to deserve it, and change your family forever.</p><p>But keeping quiet means looking him in the eyes every day while carrying a truth he might believe he has a right to know.</p><p>So which is the greater betrayal?</p><p><strong>Keeping the secret?</strong></p><p><strong>Or confessing simply because you can no longer bear the weight of carrying it alone?</strong></p><p>There is a moment many people who have cheated eventually arrive at.</p><p>It does not happen the same day.<br>Sometimes not the same year.</p><p>But sooner or later, the question appears.</p><p>Quietly.<br>Relentlessly.</p><p><em>Should I tell him?</em></p><p>Not because anyone asked.<br>Not because the secret was discovered.</p><p>But because the weight of knowing begins to press on the chest in a way that ordinary life cannot silence.</p><p>Some women carry that question for years.</p><p>They sit across from their husbands at dinner and wonder if honesty would destroy everything or finally set them free.</p><p>They watch him laughing with the children and feel a wave of tenderness followed by something darker.</p><p>A thought.</p><p><em>If he knew who I really am, would he still love me?</em></p><p>This is where the real story begins.</p><p>Not the affair.<br>Not the moment it happened.</p><p>But the life that follows after it.</p><p>Because once guilt enters a marriage, the person carrying it must decide what to do with it.</p><p>And none of the options are simple.</p><p>Some women decide never to tell.</p><p>They convince themselves that silence protects everyone.</p><p>The marriage continues.<br>The family remains intact.<br>Life moves forward.</p><p>And on the surface, it often works.</p><p>Many marriages in the world are quietly held together by things that were never spoken.</p><p>But silence has its own cost.</p><p>Secrets reshape people.</p><p>Sometimes the woman becomes distant without realizing it.<br>Sometimes she overcompensates with affection.<br>Sometimes every disagreement suddenly feels more fragile because the truth sits quietly in the background.</p><p>The marriage survives.</p><p>But inside her mind the conversation never truly ends.</p><p>Then there are women who decide they must confess.</p><p>They cannot carry it anymore.</p><p>They sit their husbands down one evening, often trembling, and say the words that change everything.</p><p>&#8220;I need to tell you something.&#8221;</p><p>That moment is unpredictable.</p><p>Some husbands explode in anger.</p><p>Some leave immediately.</p><p>Some sit there in silence as if the air has been removed from the room.</p><p>And sometimes something stranger happens.</p><p>They ask questions.</p><p>Not because the pain is small.<br>But because human beings often want to understand what broke before they decide whether something can be repaired.</p><p>But confession is not a magic cure.</p><p>Many people imagine that telling the truth automatically heals guilt.</p><p>Sometimes it does.</p><p>But it also transfers the weight.</p><p>The secret is no longer carried by one person.</p><p>Now it belongs to both.</p><p>The husband must decide what this means for him.</p><p>His pride.<br>His trust.<br>His sense of masculinity.</p><p>And that is not always easy.</p><p>Infidelity can wound a man in places he does not even know how to describe.</p><p>Not just the betrayal.</p><p>But the image he had of the relationship.</p><p>The certainty.</p><p>The quiet belief that the home he built was safe.</p><p>Some men forgive.</p><p>Not because they are weak.</p><p>But because they see the whole story.</p><p>The years together.<br>The children.<br>The life built piece by piece.</p><p>They decide the marriage is bigger than the mistake.</p><p>Other men cannot recover from it.</p><p>Not because they do not love their wives.</p><p>But because trust, once fractured, can feel impossible to rebuild.</p><p>And so the question becomes even more complicated.</p><p>Is confession always the right answer?</p><p>The truth is uncomfortable.</p><p>Sometimes confession helps a marriage grow stronger.</p><p>Sometimes it destroys it.</p><p>There is no universal formula.</p><p>That is the part no one wants to admit.</p><p>What matters more than the act itself is what happens afterward.</p><p>Did the affair reveal something broken in the marriage that needs attention?</p><p>Was it loneliness?<br>Neglect?<br>Emotional distance?<br>A search for validation?</p><p>Or was it simply a reckless moment that should never have happened?</p><p>The answers matter.</p><p>Because without understanding the root, the guilt never truly leaves.</p><p>A person can confess and still carry shame for years.</p><p>Or they can stay silent but spend the rest of their lives quietly trying to become better partners.</p><p>This is where maturity enters the conversation.</p><p>Not perfection.</p><p>Maturity.</p><p>Because relationships survive not because people never make mistakes.</p><p>They survive because two people decide how they will deal with the truth of being human.</p><p>For a woman living with this guilt, the first step is honesty with herself.</p><p>Not excuses.<br>Not denial.</p><p>Honesty.</p><p>Why did it happen?</p><p>What was missing?</p><p>What part of herself was she trying to satisfy in that moment?</p><p>Only when those questions are answered honestly can the next decision make sense.</p><p>Whether she chooses silence or confession, one thing remains essential.</p><p>The person she becomes afterward must be different.</p><p>More present.</p><p>More aware.</p><p>More intentional about the marriage she still has.</p><p>Guilt, if it is faced honestly, can become something strange.</p><p>Not a prison.</p><p>But a turning point.</p><p>Because the worst mistake a person can make is not the moment they crossed the line.</p><p>The worst mistake is refusing to learn anything from it.</p><p>And that is the question every person living with this secret must eventually answer.</p><p>Not just <em>should I tell?</em></p><p>But something deeper.</p><p><em>Who will I become after what happened?</em></p><h3><strong>WHAT DO YOU THINK?</strong></h3><p>Perhaps there is no answer that leaves everyone untouched.</p><p>So I want to leave the question with you:</p><p><strong>If your partner cheated once, genuinely regretted it and you would otherwise never know, would you want them to tell you?</strong></p><p>And if you were the one who cheated, <strong>would you confess?</strong></p><h3><strong>SUPPORT THE DIARY</strong></h3><p>If these conversations make you think, feel or see relationships differently, consider becoming a paid subscriber. Your support helps me keep writing <em>The Diary of a Playboy</em> and taking these conversations deeper.</p><p>Thank you for reading, whether you&#8217;re a free or paid subscriber.</p><p>Until next time, perhaps honesty is not only about telling the truth. Sometimes it is also about being prepared to live with what the truth does once it is spoken.</p><p><strong>Martins Itua</strong></p><div class="subscription-widget-wrap-editor" data-attrs="{&quot;url&quot;:&quot;https://thediaryofaplayboy.substack.com/subscribe?&quot;,&quot;text&quot;:&quot;Subscribe&quot;,&quot;language&quot;:&quot;en&quot;}" data-component-name="SubscribeWidgetToDOM"><div class="subscription-widget show-subscribe"><div class="preamble"><p class="cta-caption">The Diary of a Playboy is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.</p></div><form class="subscription-widget-subscribe"><input type="email" class="email-input" name="email" placeholder="Type your email&#8230;" tabindex="-1"><input type="submit" class="button primary" value="Subscribe"><div class="fake-input-wrapper"><div class="fake-input"></div><div class="fake-button"></div></div></form></div></div>]]></content:encoded></item><item><title><![CDATA[SHE CHEATED. HER HUSBAND NEVER FOUND OUT]]></title><description><![CDATA[The Weight of What Happened]]></description><link>https://thediaryofaplayboy.substack.com/p/she-cheated-her-husband-never-found</link><guid isPermaLink="false">https://thediaryofaplayboy.substack.com/p/she-cheated-her-husband-never-found</guid><dc:creator><![CDATA[Martins Itua]]></dc:creator><pubDate>Sat, 12 Sep 2026 16:28:57 GMT</pubDate><enclosure url="iframe.php?url=https%3A%2F%2Fsubstackcdn.com%2Fimage%2Ffetch%2F%24s_%218iBu%21%2Cf_auto%2Cq_auto%3Agood%2Cfl_progressive%3Asteep%2Fhttps%253A%252F%252Fsubstack-post-media.s3.amazonaws.com%252Fpublic%252Fimages%252F66c76e26-eced-444f-883e-534956966143_1099x1431.png" length="0" type="image/jpeg"/><content:encoded><![CDATA[<p><strong>A NOTE BEFORE YOU READ</strong></p><p>I first shared this piece some time ago, but the question at the heart of it has never really left me.</p><p>What happens when someone cheats, regrets it deeply, and the person they betrayed never finds out?</p><p>We talk endlessly about infidelity from the perspective of the person who was betrayed. We talk about anger, broken trust, forgiveness and whether a relationship can survive.</p><p>But there is another side we rarely talk about.</p><p>The person who did it.</p><p>What happens when she goes home? When she sits across from the man she still loves? When he smiles at her without knowing? When months become years and the secret remains?</p><p>Does guilt eventually fade?</p><p>Or does carrying a secret begin to change the person carrying it?</p><p>I wanted to revisit this piece because those questions are still worth asking.</p><p>Not to excuse betrayal.</p><p>Not to condemn anyone.</p><p>But to understand what happens when one terrible decision becomes something you have to live beside every day.</p><div class="captioned-image-container"><figure><a class="image-link image2 is-viewable-img" target="_blank" href="iframe.php?url=https%3A%2F%2Fsubstackcdn.com%2Fimage%2Ffetch%2F%24s_%218iBu%21%2Cf_auto%2Cq_auto%3Agood%2Cfl_progressive%3Asteep%2Fhttps%253A%252F%252Fsubstack-post-media.s3.amazonaws.com%252Fpublic%252Fimages%252F66c76e26-eced-444f-883e-534956966143_1099x1431.png" data-component-name="Image2ToDOM"><div class="image2-inset"><picture><source type="image/webp" srcset="https://substackcdn.com/image/fetch/$s_!8iBu!,w_424,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F66c76e26-eced-444f-883e-534956966143_1099x1431.png 424w, https://substackcdn.com/image/fetch/$s_!8iBu!,w_848,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F66c76e26-eced-444f-883e-534956966143_1099x1431.png 848w, https://substackcdn.com/image/fetch/$s_!8iBu!,w_1272,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F66c76e26-eced-444f-883e-534956966143_1099x1431.png 1272w, https://substackcdn.com/image/fetch/$s_!8iBu!,w_1456,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F66c76e26-eced-444f-883e-534956966143_1099x1431.png 1456w" sizes="auto, 100vw"><img src="iframe.php?url=https%3A%2F%2Fsubstackcdn.com%2Fimage%2Ffetch%2F%24s_%218iBu%21%2Cw_1456%2Cc_limit%2Cf_auto%2Cq_auto%3Agood%2Cfl_progressive%3Asteep%2Fhttps%253A%252F%252Fsubstack-post-media.s3.amazonaws.com%252Fpublic%252Fimages%252F66c76e26-eced-444f-883e-534956966143_1099x1431.png" width="1099" height="1431" 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srcset="https://substackcdn.com/image/fetch/$s_!8iBu!,w_424,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F66c76e26-eced-444f-883e-534956966143_1099x1431.png 424w, https://substackcdn.com/image/fetch/$s_!8iBu!,w_848,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F66c76e26-eced-444f-883e-534956966143_1099x1431.png 848w, https://substackcdn.com/image/fetch/$s_!8iBu!,w_1272,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F66c76e26-eced-444f-883e-534956966143_1099x1431.png 1272w, https://substackcdn.com/image/fetch/$s_!8iBu!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F66c76e26-eced-444f-883e-534956966143_1099x1431.png 1456w" sizes="auto, 100vw" loading="lazy"></picture><div class="image-link-expand"><div class="pencraft pc-display-flex pc-gap-8 pc-reset"><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container restack-image buttonBase-GK1x3M"><svg aria-hidden="true" width="20" height="20" viewBox="0 0 20 20" fill="none" stroke-width="1.5" stroke="var(--color-fg-primary)" stroke-linecap="round" stroke-linejoin="round" xmlns="http://www.w3.org/2000/svg" class="icon-noB79L"><g><path d="M2.53001 7.81595C3.49179 4.73911 6.43281 2.5 9.91173 2.5C13.1684 2.5 15.9537 4.46214 17.0852 7.23684L17.6179 8.67647M17.6179 8.67647L18.5002 4.26471M17.6179 8.67647L13.6473 6.91176M17.4995 12.1841C16.5378 15.2609 13.5967 17.5 10.1178 17.5C6.86118 17.5 4.07589 15.5379 2.94432 12.7632L2.41165 11.3235M2.41165 11.3235L1.5293 15.7353M2.41165 11.3235L6.38224 13.0882"></path></g></svg></button><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container view-image buttonBase-GK1x3M"><svg xmlns="http://www.w3.org/2000/svg" width="20" height="20" viewBox="0 0 24 24" fill="none" stroke="currentColor" stroke-width="2" stroke-linecap="round" stroke-linejoin="round" class="lucide lucide-maximize2 lucide-maximize-2 icon-noB79L"><polyline points="15 3 21 3 21 9"></polyline><polyline points="9 21 3 21 3 15"></polyline><line x1="21" x2="14" y1="3" y2="10"></line><line x1="3" x2="10" y1="21" y2="14"></line></svg></button></div></div></div></a></figure></div><p><span>There are things people do that the world never finds out.</span></p><p><span>Not because they are proud of them.<br>But because the truth would change how everyone looks at them.</span></p><p><span>Cheating is one of those things.</span></p><p><span>For centuries people have talked about infidelity as if it belongs mostly to men. Men have had mistresses, second families, secret apartments, and society has often shrugged. Sometimes it is even joked about.</span></p><p><span>But when a woman cheats, the world becomes very different.</span></p><p><span>Suddenly there is outrage. Judgment. Shame. In some cultures, punishment.</span></p><p><span>Yet beneath the noise of society is something much quieter and far more painful.</span></p><p><span>Guilt.</span></p><p><span>Not the kind people talk about loudly.<br>The silent kind that lives in the chest.<br>The kind that wakes someone at night.</span></p><p><span>Today I want to talk about that weight.<br>Not to condemn anyone.<br>Not to excuse anything.</span></p><p><span>But to understand what it does to the people who carry it.</span></p><p><span>Because somewhere right now, a woman is living with something she cannot say out loud.</span></p><p><span>People imagine cheating as a moment.</span></p><p><span>A hotel room.<br>A text message.<br>A kiss that should not have happened.</span></p><p><span>But for the person who carries the memory, it rarely stays a moment.</span></p><p><span>It becomes something else.</span></p><p><span>A quiet presence.</span></p><p><span>She might still be married.<br>Still cooking dinner.<br>Still laughing at family gatherings.</span></p><p><span>But sometimes she looks at her partner and remembers what she did.</span></p><p><span>And the room becomes heavy.</span></p><p><span>Not because she stopped loving him.<br>But because guilt has a strange way of sitting between people who do not even know it is there.</span></p><p><span>Many women who cheat do not talk about it afterward.</span></p><p><span>Not to friends.<br>Not to family.<br>Not even to themselves.</span></p><p><span>They bury it.</span></p><p><span>But buried things have a way of breathing underground.</span></p><p><span>The outside world rarely sees the inner conflict.</span></p><p><span>People assume that if someone cheated, it must mean they did not care.<br>Or that they are reckless.<br>Or heartless.</span></p><div class="captioned-image-container"><figure><a class="image-link image2 is-viewable-img" target="_blank" href="iframe.php?url=https%3A%2F%2Fsubstackcdn.com%2Fimage%2Ffetch%2F%24s_%21pZU0%21%2Cf_auto%2Cq_auto%3Agood%2Cfl_progressive%3Asteep%2Fhttps%253A%252F%252Fsubstack-post-media.s3.amazonaws.com%252Fpublic%252Fimages%252Fc6b23393-8fd0-4904-a16a-08d9004b43f6_554x721.jpeg" data-component-name="Image2ToDOM"><div class="image2-inset"><picture><source type="image/webp" srcset="https://substackcdn.com/image/fetch/$s_!pZU0!,w_424,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fc6b23393-8fd0-4904-a16a-08d9004b43f6_554x721.jpeg 424w, https://substackcdn.com/image/fetch/$s_!pZU0!,w_848,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fc6b23393-8fd0-4904-a16a-08d9004b43f6_554x721.jpeg 848w, https://substackcdn.com/image/fetch/$s_!pZU0!,w_1272,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fc6b23393-8fd0-4904-a16a-08d9004b43f6_554x721.jpeg 1272w, https://substackcdn.com/image/fetch/$s_!pZU0!,w_1456,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fc6b23393-8fd0-4904-a16a-08d9004b43f6_554x721.jpeg 1456w" sizes="auto, 100vw"><img src="iframe.php?url=https%3A%2F%2Fsubstackcdn.com%2Fimage%2Ffetch%2F%24s_%21pZU0%21%2Cw_1456%2Cc_limit%2Cf_auto%2Cq_auto%3Agood%2Cfl_progressive%3Asteep%2Fhttps%253A%252F%252Fsubstack-post-media.s3.amazonaws.com%252Fpublic%252Fimages%252Fc6b23393-8fd0-4904-a16a-08d9004b43f6_554x721.jpeg" width="554" height="721" data-attrs="{&quot;src&quot;:&quot;https://substack-post-media.s3.amazonaws.com/public/images/c6b23393-8fd0-4904-a16a-08d9004b43f6_554x721.jpeg&quot;,&quot;srcNoWatermark&quot;:null,&quot;fullscreen&quot;:null,&quot;imageSize&quot;:null,&quot;height&quot;:721,&quot;width&quot;:554,&quot;resizeWidth&quot;:null,&quot;bytes&quot;:40438,&quot;alt&quot;:null,&quot;title&quot;:null,&quot;type&quot;:&quot;image/jpeg&quot;,&quot;href&quot;:null,&quot;belowTheFold&quot;:true,&quot;topImage&quot;:false,&quot;internalRedirect&quot;:&quot;https://thediaryofaplayboy.substack.com/i/215384062?img=https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fc6b23393-8fd0-4904-a16a-08d9004b43f6_554x721.jpeg&quot;,&quot;isProcessing&quot;:false,&quot;align&quot;:null,&quot;offset&quot;:false}" class="sizing-normal" alt="" srcset="https://substackcdn.com/image/fetch/$s_!pZU0!,w_424,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fc6b23393-8fd0-4904-a16a-08d9004b43f6_554x721.jpeg 424w, https://substackcdn.com/image/fetch/$s_!pZU0!,w_848,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fc6b23393-8fd0-4904-a16a-08d9004b43f6_554x721.jpeg 848w, https://substackcdn.com/image/fetch/$s_!pZU0!,w_1272,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fc6b23393-8fd0-4904-a16a-08d9004b43f6_554x721.jpeg 1272w, https://substackcdn.com/image/fetch/$s_!pZU0!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fc6b23393-8fd0-4904-a16a-08d9004b43f6_554x721.jpeg 1456w" sizes="auto, 100vw" loading="lazy"></picture><div class="image-link-expand"><div class="pencraft pc-display-flex pc-gap-8 pc-reset"><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container restack-image buttonBase-GK1x3M"><svg aria-hidden="true" width="20" height="20" viewBox="0 0 20 20" fill="none" stroke-width="1.5" stroke="var(--color-fg-primary)" stroke-linecap="round" stroke-linejoin="round" xmlns="http://www.w3.org/2000/svg" class="icon-noB79L"><g><path d="M2.53001 7.81595C3.49179 4.73911 6.43281 2.5 9.91173 2.5C13.1684 2.5 15.9537 4.46214 17.0852 7.23684L17.6179 8.67647M17.6179 8.67647L18.5002 4.26471M17.6179 8.67647L13.6473 6.91176M17.4995 12.1841C16.5378 15.2609 13.5967 17.5 10.1178 17.5C6.86118 17.5 4.07589 15.5379 2.94432 12.7632L2.41165 11.3235M2.41165 11.3235L1.5293 15.7353M2.41165 11.3235L6.38224 13.0882"></path></g></svg></button><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container view-image buttonBase-GK1x3M"><svg xmlns="http://www.w3.org/2000/svg" width="20" height="20" viewBox="0 0 24 24" fill="none" stroke="currentColor" stroke-width="2" stroke-linecap="round" stroke-linejoin="round" class="lucide lucide-maximize2 lucide-maximize-2 icon-noB79L"><polyline points="15 3 21 3 21 9"></polyline><polyline points="9 21 3 21 3 15"></polyline><line x1="21" x2="14" y1="3" y2="10"></line><line x1="3" x2="10" y1="21" y2="14"></line></svg></button></div></div></div></a></figure></div><p></p><p><span>But life is rarely that simple.</span></p><p><span>Consider a woman who married young.</span></p><p><span>Her husband is decent. Responsible. A good father. A provider.</span></p><p><span>But over the years something between them faded.</span></p><p><span>Not love exactly.<br>More like presence.</span></p><p><span>They stopped talking deeply.<br>Stopped touching with curiosity.<br>Stopped seeing each other.</span></p><p><span>Then somewhere in the middle of ordinary life she met someone who saw her differently.</span></p><p><span>He noticed her.<br>Listened.<br>Looked at her in a way that reminded her she was still alive.</span></p><p><span>Sometimes that is all it takes.</span></p><p><span>One conversation.<br>One moment of emotional closeness.</span></p><p><span>And suddenly she crosses a line she never imagined she would cross.</span></p><p><span>The act itself may last minutes or hours.</span></p><p><span>But the consequences can live for years.</span></p><p><span>Because afterward, she goes home.</span></p><p><span>And everything looks the same.</span></p><p><span>Except she is not the same anymore.</span></p><p><span>One of the cruellest parts of guilt is that it is often silent.</span></p><p><span>A woman who cheated cannot easily tell her friends.</span></p><p><span>Friends judge.</span></p><p><span>Society judges even faster.</span></p><p><span>So she continues living normally while carrying something heavy inside her.</span></p><p><span>Sometimes it shows up in strange ways.</span></p><p><span>She becomes overly patient with her husband.<br>Or distant.<br>Or suddenly generous.</span></p><p><span>Sometimes she avoids certain conversations.</span></p><p><span>Sometimes she overthinks every argument.</span></p><p><span>Because inside her mind there is always one question:</span></p><p><em><span>If he knew&#8230; what would happen?</span></em></p><p><span>Would the marriage end?</span></p><p><span>Would the children be affected?</span></p><p><span>Would the years together suddenly mean nothing?</span></p><p><span>And so she lives between two realities.</span></p><p><span>The life everyone sees.<br>And the truth she keeps inside.</span></p><p><span>Part of the reason guilt feels unbearable is because many women never imagined themselves capable of cheating.</span></p><p><span>They were the loyal ones.</span></p><p><span>The ones who judged others for doing it.</span></p><p><span>The ones who said </span><em><span>&#8220;I would never do that.&#8221;</span></em></p><p><span>When someone crosses a line they once believed defined their character, the conflict becomes deeper.</span></p><p><span>It is no longer just about the act.</span></p><p><span>It becomes about identity.</span></p><p><em><span>Who am I now?</span></em></p><p><span>Am I still the person I thought I was?</span></p><p><span>Or was I always capable of this?</span></p><p><span>Those questions can haunt someone far more than the act itself.</span></p><p><span>Many women living with guilt ask themselves something terrifying.</span></p><p><span>Not out loud.</span></p><p><span>But in quiet moments.</span></p><p><span>Was it worth it?</span></p><p><span>Not because the experience was meaningless.</span></p><p><span>Sometimes it was passionate.<br>Sometimes it was emotional.<br>Sometimes it was a moment of feeling alive again.</span></p><p><span>But afterward comes the cost.</span></p><p><span>The silence.<br>The fear.<br>The internal conversation that never stops.</span></p><p><span>And the realization that choices, even small ones, can echo through years.</span></p><p><span>Yet there is another truth many people do not want to admit.</span></p><p><span>Human beings are complicated.</span></p><p><span>People can love their partners and still make terrible decisions.</span></p><p><span>They can regret something deeply while still being the same person who tries to be a good partner, a good mother, a good human being.</span></p><p><span>Life is not always divided into saints and villains.</span></p><p><span>Sometimes it is just people navigating loneliness, desire, attention, and mistakes.</span></p><p><span>Understanding that complexity does not erase the damage.</span></p><p><span>But it helps explain why guilt can become such a heavy emotional burden.</span></p><p><span>If someone is living with this kind of guilt, the hardest part is often the silence.</span></p><p><span>Carrying something alone for years can slowly reshape a person.</span></p><h3><strong>TO BE CONTINUED...</strong></h3><p>But guilt eventually leaves you with another question:</p><p><strong>If he never found out, should you tell him?</strong></p><p>That is where Part Two begins.</p><h3><strong>SUPPORT THE DIARY</strong></h3><p>If these conversations make you think, feel, or see relationships differently, consider becoming a <a href="iframe.php?url=https%3A%2F%2Fthediaryofaplayboy.substack.com%2Fsubscribe%3F">Paid Subscriber</a>. Your support helps me keep writing <em>The Diary of a Playboy</em> and taking these conversations deeper.</p><p>Thank you for reading, whether you&#8217;re a free or paid subscriber.</p><p><strong>Before Part Two, I'd really like to know: if someone cheats once, genuinely regrets it and their partner never finds out, should they confess?</strong></p><p>Until next time, remember that sometimes the heaviest consequences of our choices are the ones nobody else can see.</p><p><strong>Martins Itua</strong></p>]]></content:encoded></item><item><title><![CDATA[BEFORE YOU WALK AWAY]]></title><description><![CDATA[The Other Side of Divorce Nobody Talks About]]></description><link>https://thediaryofaplayboy.substack.com/p/before-you-walk-away</link><guid isPermaLink="false">https://thediaryofaplayboy.substack.com/p/before-you-walk-away</guid><dc:creator><![CDATA[Martins Itua]]></dc:creator><pubDate>Tue, 08 Sep 2026 13:55:28 GMT</pubDate><enclosure url="iframe.php?url=https%3A%2F%2Fsubstackcdn.com%2Fimage%2Ffetch%2F%24s_%21LVPE%21%2Cf_auto%2Cq_auto%3Agood%2Cfl_progressive%3Asteep%2Fhttps%253A%252F%252Fsubstack-post-media.s3.amazonaws.com%252Fpublic%252Fimages%252F77ef3fa6-de60-4867-a193-520cf15fe81f_1024x1536.png" length="0" type="image/jpeg"/><content:encoded><![CDATA[<p>Some marriages should end.</p><p>Let us begin there.</p><div class="subscription-widget-wrap-editor" data-attrs="{&quot;url&quot;:&quot;https://thediaryofaplayboy.substack.com/subscribe?&quot;,&quot;text&quot;:&quot;Subscribe&quot;,&quot;language&quot;:&quot;en&quot;}" data-component-name="SubscribeWidgetToDOM"><div class="subscription-widget show-subscribe"><div class="preamble"><p class="cta-caption">The Diary of a Playboy is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.</p></div><form class="subscription-widget-subscribe"><input type="email" class="email-input" name="email" placeholder="Type your email&#8230;" tabindex="-1"><input type="submit" class="button primary" value="Subscribe"><div class="fake-input-wrapper"><div class="fake-input"></div><div class="fake-button"></div></div></form></div></div><p>There are marriages where leaving is not giving up. It is survival. Where there is violence, abuse, coercion, persistent betrayal or the gradual destruction of someone&#8217;s dignity, walking away may be the healthiest decision a person can make.</p><p>But not every broken marriage is an irredeemable marriage.</p><p>And perhaps that is the uncomfortable conversation we don&#8217;t have enough.</p><p>We spend months preparing for weddings and remarkably little time preparing for marriage.</p><p>We discuss venues, clothes, rings, photographs, guest lists and honeymoons.</p><p>But did you ever ask the person you were marrying what would happen if one of you cheated?</p><p>Is infidelity automatically the end?</p><p>What constitutes cheating?</p><p>What happens when sex becomes infrequent?</p><p>How will you manage money?</p><p>Children?</p><p>In-laws?</p><p>Jealousy?</p><p>Career disappointments?</p><p>What happens when you are both furious?</p><p>Can you disagree without insulting each other?</p><p>Can you fight without threatening divorce?</p><p>Can you forgive something you once swore you never would?</p><p>Perhaps most importantly, what happens when the person you married becomes someone different?</p><p>Because they will.</p><p>And so will you.</p><p>Marriage does not freeze two people on their wedding day. Life happens to them. Children arrive. Parents die. Money comes and goes. Bodies change. Careers rise and collapse. Sex changes. Illness happens. Dreams evolve. People disappoint each other.</p><p>Then one day, someone says:</p><p><em>I can&#8217;t do this anymore.</em></p><p>And sometimes they are absolutely right.</p><p>But sometimes those words are spoken at the height of anger, betrayal, exhaustion or resentment, when leaving appears to offer something intoxicating.</p><p><strong>Freedom.</strong></p><p>No more arguments.</p><p>No more explaining yourself.</p><p>No more coming home to someone who makes you unhappy.</p><p>A fresh start.</p><p>Perhaps even somebody new.</p><p>But anger has a peculiar way of showing us the door without showing us what is on the other side of it.</p><p>It doesn&#8217;t show you the first night alone when the silence feels different from the freedom you imagined.</p><p>It doesn&#8217;t show you another man helping your son with his homework.</p><p>Or another woman sitting beside your daughter at breakfast.</p><p>It doesn&#8217;t show you Christmas negotiated through a custody schedule.</p><p>Birthdays divided between homes.</p><p>The child who learns to pack a weekend bag because Mummy and Daddy no longer live together.</p><p>It doesn&#8217;t show you hearing your former spouse&#8217;s version of your marriage coming from the mouth of your own child.</p><p>And it certainly doesn&#8217;t tell you that you can desperately miss the family you had while still knowing you should never return to the marriage you left.</p><p>None of this means divorce is wrong.</p><p>Sometimes divorce is necessary. Sometimes it should even be celebrated because somebody finally found the courage to leave something destructive.</p><p>But necessary decisions can still have painful consequences.</p><p>And before we turn <em>&#8220;choose yourself&#8221;</em> into universal relationship advice, perhaps we should ask one brutally difficult question:</p><p><strong>Before you walked away, did you know whether the marriage was truly beyond saving?</strong></p><div class="captioned-image-container"><figure><a class="image-link image2 is-viewable-img" target="_blank" href="iframe.php?url=https%3A%2F%2Fsubstackcdn.com%2Fimage%2Ffetch%2F%24s_%21LVPE%21%2Cf_auto%2Cq_auto%3Agood%2Cfl_progressive%3Asteep%2Fhttps%253A%252F%252Fsubstack-post-media.s3.amazonaws.com%252Fpublic%252Fimages%252F77ef3fa6-de60-4867-a193-520cf15fe81f_1024x1536.png" data-component-name="Image2ToDOM"><div class="image2-inset"><picture><source type="image/webp" srcset="https://substackcdn.com/image/fetch/$s_!LVPE!,w_424,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F77ef3fa6-de60-4867-a193-520cf15fe81f_1024x1536.png 424w, https://substackcdn.com/image/fetch/$s_!LVPE!,w_848,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F77ef3fa6-de60-4867-a193-520cf15fe81f_1024x1536.png 848w, https://substackcdn.com/image/fetch/$s_!LVPE!,w_1272,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F77ef3fa6-de60-4867-a193-520cf15fe81f_1024x1536.png 1272w, https://substackcdn.com/image/fetch/$s_!LVPE!,w_1456,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F77ef3fa6-de60-4867-a193-520cf15fe81f_1024x1536.png 1456w" sizes="auto, 100vw"><img src="iframe.php?url=https%3A%2F%2Fsubstackcdn.com%2Fimage%2Ffetch%2F%24s_%21LVPE%21%2Cw_1456%2Cc_limit%2Cf_auto%2Cq_auto%3Agood%2Cfl_progressive%3Asteep%2Fhttps%253A%252F%252Fsubstack-post-media.s3.amazonaws.com%252Fpublic%252Fimages%252F77ef3fa6-de60-4867-a193-520cf15fe81f_1024x1536.png" width="1024" height="1536" 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srcset="https://substackcdn.com/image/fetch/$s_!LVPE!,w_424,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F77ef3fa6-de60-4867-a193-520cf15fe81f_1024x1536.png 424w, https://substackcdn.com/image/fetch/$s_!LVPE!,w_848,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F77ef3fa6-de60-4867-a193-520cf15fe81f_1024x1536.png 848w, https://substackcdn.com/image/fetch/$s_!LVPE!,w_1272,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F77ef3fa6-de60-4867-a193-520cf15fe81f_1024x1536.png 1272w, https://substackcdn.com/image/fetch/$s_!LVPE!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F77ef3fa6-de60-4867-a193-520cf15fe81f_1024x1536.png 1456w" sizes="auto, 100vw" loading="lazy"></picture><div class="image-link-expand"><div class="pencraft pc-display-flex pc-gap-8 pc-reset"><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container restack-image buttonBase-GK1x3M"><svg aria-hidden="true" width="20" height="20" viewBox="0 0 20 20" fill="none" stroke-width="1.5" stroke="var(--color-fg-primary)" stroke-linecap="round" stroke-linejoin="round" xmlns="http://www.w3.org/2000/svg" class="icon-noB79L"><g><path d="M2.53001 7.81595C3.49179 4.73911 6.43281 2.5 9.91173 2.5C13.1684 2.5 15.9537 4.46214 17.0852 7.23684L17.6179 8.67647M17.6179 8.67647L18.5002 4.26471M17.6179 8.67647L13.6473 6.91176M17.4995 12.1841C16.5378 15.2609 13.5967 17.5 10.1178 17.5C6.86118 17.5 4.07589 15.5379 2.94432 12.7632L2.41165 11.3235M2.41165 11.3235L1.5293 15.7353M2.41165 11.3235L6.38224 13.0882"></path></g></svg></button><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container view-image buttonBase-GK1x3M"><svg xmlns="http://www.w3.org/2000/svg" width="20" height="20" viewBox="0 0 24 24" fill="none" stroke="currentColor" stroke-width="2" stroke-linecap="round" stroke-linejoin="round" class="lucide lucide-maximize2 lucide-maximize-2 icon-noB79L"><polyline points="15 3 21 3 21 9"></polyline><polyline points="9 21 3 21 3 15"></polyline><line x1="21" x2="14" y1="3" y2="10"></line><line x1="3" x2="10" y1="21" y2="14"></line></svg></button></div></div></div></a></figure></div><h2><strong>Was It Really the Marriage?</strong></h2><p>Sometimes when people say, <em>&#8220;The marriage stopped working,&#8221;</em> I wonder what that actually means.</p><p>Because marriages rarely collapse in a vacuum.</p><p>Look underneath many unhappy marriages and you will find the same forces waiting there.</p><p>Money.</p><p>Sex.</p><p>Resentment.</p><p>Family.</p><p>Children.</p><p>And conversations that should have happened years ago.</p><p>Money is particularly deceptive.</p><p>Too little of it creates pressure. Bills become arguments. One person feels they are carrying the family. The other feels constantly judged. Every purchase becomes a negotiation.</p><p>But too much money can create its own problems.</p><p>Success can change power inside a marriage. It can create independence, entitlement, temptation and opportunity. The person who once needed the marriage may suddenly discover that they no longer believe they do.</p><p>Then there is sex.</p><p>Too little.</p><p>Too predictable.</p><p>Withheld as punishment.</p><p>Wanted by one person more than the other.</p><p>Or found outside the marriage.</p><p>Sex is rarely <em>just</em> sex in a marriage. It can become rejection, validation, power, insecurity, intimacy and betrayal all at once.</p><p>And what happens when somebody cheats?</p><p>We are quick to say, <em>&#8220;Leave.&#8221;</em></p><p>Perhaps that is the right answer.</p><p>But did the couple themselves ever decide that?</p><p>Did you ever sit across from the person you intended to spend your life with and ask:</p><p><em>If I am unfaithful one day, is our marriage automatically over?</em></p><p>It is an uncomfortable conversation.</p><p>Maybe that is precisely why it should happen before the wedding.</p><p>Then there are unresolved conflicts.</p><p>The argument that supposedly ended on Tuesday but quietly joined the argument from six months ago.</p><p>Apologies never offered.</p><p>Words never forgotten.</p><p>Sex withheld.</p><p>Silence weaponised.</p><p>Small resentments deposited repeatedly until one morning two people wake up emotionally bankrupt.</p><p>Sometimes marriages don&#8217;t die from one enormous wound.</p><p><strong>They bleed to death from a thousand untreated cuts.</strong></p><p>And then there is family.</p><p>The mother who cannot release her son.</p><p>The spouse who tells their siblings everything.</p><p>The in-law who has an opinion about every decision.</p><p>The family member whose disrespect is continually excused because <em>&#8220;that&#8217;s just how they are.&#8221;</em></p><p>Eventually somebody begins wondering whether they married one person or an entire family.</p><p>And perhaps the most uncomfortable pressure of all is the one nobody wants to blame.</p><p>The children.</p><p>Children can be one of marriage&#8217;s greatest joys and still test the marriage that created them.</p><p>A baby arrives and sleep disappears.</p><p>Attention shifts.</p><p>Sex changes.</p><p>Money becomes tighter.</p><p>One parent may feel abandoned while the other feels overwhelmed.</p><p>Then come disagreements about discipline, schools, religion, money and whose career should make the greater sacrifice.</p><p>Sometimes a couple becomes so busy being Mum and Dad that they forget how to be husband and wife.</p><p>Years later, they look across the room and realise they have become excellent co-parents and complete strangers.</p><p>None of these things means people should remain in marriages that have become destructive.</p><p>But they raise a question worth asking before we declare the marriage itself to be the problem:</p><p><strong>Are you trying to escape the person, or are two exhausted people failing to confront the problems that have slowly come between them?</strong></p><p>Because changing spouses does not automatically change your relationship with money.</p><p>It does not resolve your attitude towards sex.</p><p>It does not teach you how to manage conflict.</p><p>It does not create boundaries with your family.</p><p>And it certainly does not remove the children you will still have to raise together.</p><p>Sometimes the problems we believe we are divorcing have an inconvenient habit of following us out the door.</p><h2><strong>Before You Decide There Is Nothing Left to Save</strong></h2><p>Here is an uncomfortable scenario.</p><p>A woman discovers that her husband has cheated.</p><p>She is devastated.</p><p>For her, infidelity is unforgivable. She leaves the marriage.</p><p>Years later, she finds herself in love with a married man.</p><p>Now she is the other woman in somebody else&#8217;s marriage.</p><p>Life has an uncomfortable way of complicating the moral positions that once seemed very simple.</p><p>This is not an argument for tolerating infidelity.</p><p>It is an argument for humility.</p><p>Because perhaps before two people who once loved each other decide that there is nothing left to save, there should be one conversation in which neither person comes armed with a prosecution.</p><p>Not:</p><p><em>Here is everything you did wrong.</em></p><p>But:</p><p><strong>Where did we go wrong?</strong></p><p>When did we stop seeing each other?</p><p>When did I stop making the effort?</p><p>When did you?</p><p>Was I so busy building a career, raising children or solving everybody else&#8217;s problems that I stopped noticing the person sleeping beside me?</p><p>When did sex become another household obligation?</p><p>When did we stop touching?</p><p>When did we stop laughing?</p><p>When did home become the place where we brought our exhaustion instead of the place where we brought our best selves?</p><p>Did I make you feel wanted?</p><p>Did you make me feel valued?</p><p>When you tried to tell me something was wrong, did I actually listen?</p><p>And perhaps the hardest question of all:</p><p><strong>What did I contribute to the distance between us?</strong></p><p>That question is difficult because anger prefers certainty.</p><p>It wants an offender and a victim.</p><p>Sometimes that distinction is entirely justified. Abuse is not created because somebody &#8220;dropped the ball.&#8221; Violence is the responsibility of the person who chooses violence. Betrayal should not be transferred onto the person betrayed.</p><p>But many failing marriages are more complicated than a courtroom with one guilty party.</p><p>Sometimes two decent people stopped doing the things that once made them good together.</p><p>And perhaps they still want the same thing.</p><p>Perhaps neither actually wants the marriage to end.</p><p>They just want <strong>this version of the marriage</strong> to end.</p><p>That distinction matters.</p><p>Can we get help?</p><p>Can we talk honestly about sex?</p><p>Can we rebuild trust?</p><p>Can we establish boundaries with our families?</p><p>Can we change how we fight?</p><p>Can we forgive?</p><p>Can we date each other again?</p><p>Can we create something different from what we have allowed this marriage to become?</p><p>Maybe the answer is no.</p><p>Sometimes too much has happened.</p><p>Sometimes trust cannot be rebuilt.</p><p>Sometimes love has genuinely gone.</p><p>And sometimes leaving remains the right decision.</p><p>But imagine discovering, years after the divorce, that what both of you desperately wanted was not freedom from each other.</p><p>You wanted freedom from the way you had learned to live together.</p><p>That is why, before you walk away, it may be worth asking one final question:</p><p><strong>Have we exhausted the marriage, or have we simply exhausted each other?</strong></p><h2><strong>And Then There Is the Other Side</strong></h2><p>Because if the answer is still <em>we have to leave</em>, then leave with your eyes open.</p><p>Divorce may give you freedom.</p><p>But freedom has consequences too.</p><p>There may be loneliness.</p><p>There may be financial pressure.</p><p>There may be dating apps and disappointing relationships and the strange experience of becoming single in a world that has changed since you last were.</p><p>There may be nights when you miss someone you still know you should never return to.</p><p>And if there are children, the consequences become even more complicated.</p><p>They did not choose the affair.</p><p>They did not create the resentment.</p><p>They did not invite the in-laws into the marriage.</p><p>They did not stop the sex.</p><p>They did not file the papers.</p><p>But they may live with the consequences for years.</p><p>They may grow up primarily in one home without the daily physical presence of the other parent.</p><p>They may learn to divide holidays.</p><p>Pack bags for weekends.</p><p>Navigate new partners.</p><p>And sometimes they inherit one parent&#8217;s version of a marriage they were too young to understand.</p><p>One of the cruellest things divorced parents can do is recruit their children into a war that belonged to adults.</p><p>Your child does not need to hate their mother because you do.</p><p>Your child does not need to believe their father was a terrible husband in order to love you.</p><p>Whatever happened between the two of you, they should not be required to carry it.</p><p>And perhaps that is the part anger rarely allows us to see.</p><p>Divorce ends a marriage.</p><p><strong>It does not end a family. It reorganises one.</strong></p><p>Everyone then has to learn how to live inside the new arrangement.</p><h2><strong>Before You Walk Away</strong></h2><p>None of this is an argument against divorce.</p><p>Some marriages should end.</p><p>Some people become safer, healthier and more themselves once they leave.</p><p>There are doors that should be closed and never reopened.</p><p>But we should be careful about romanticising either side.</p><p>Marriage is not always the happy ending.</p><p>Divorce is not always freedom.</p><p>Sometimes staying requires courage.</p><p>Sometimes leaving requires courage.</p><p>And sometimes the greatest courage is sitting across from someone who has hurt you, putting down the list of accusations for a moment and asking:</p><p><em>Is there anything here worth saving?</em></p><p>If the answer is yes, perhaps fight for it differently.</p><p>If the answer is no, then walk away knowing you asked the questions anger did not want you to ask.</p><p>Because the purpose of looking carefully before you leave is not to remain trapped.</p><p>It is to make sure that when you finally close the door, <strong>you understand what you are leaving, why you are leaving it, and what may be waiting on the other side.</strong></p><p>Thank you for reading.</p><p>If you&#8217;re new here, welcome to <em>The Diary of a Playboy</em>, where we have honest conversations about love, relationships, heartbreak, family and the complicated choices that shape our lives.</p><p>And to those who continue to read, comment, disagree and share your own experiences, thank you. These conversations are richer because you are part of them.</p><p>I&#8217;d really like to hear your thoughts on this one:</p><p><strong>When do you believe a marriage becomes truly irredeemable? And how do two people know they have genuinely done enough before walking away?</strong></p><p>Until next time, love honestly, talk before silence becomes resentment, and never make a permanent decision from a temporary moment of anger.</p><p><strong>Martins Itua</strong></p><p><a href="iframe.php?url=https%3A%2F%2Fthediaryofaplayboy.substack.com%2Fp%2Fhow-to-have-difficult-conversations%3Fr%3Dhyiy3%26amp%3Butm_campaign%3Dpost%26amp%3Butm_medium%3Dweb">HOW TO HAVE DIFFICULT CONVERSATIONS IN A RELATIONSHIP</a></p><p><a href="iframe.php?url=https%3A%2F%2Fthediaryofaplayboy.substack.com%2Fp%2Fwhen-intimacy-becomes-ammunition%3Fr%3Dhyiy3%26amp%3Butm_campaign%3Dpost%26amp%3Butm_medium%3Dweb">When Intimacy Becomes Ammunition</a></p><div class="subscription-widget-wrap-editor" data-attrs="{&quot;url&quot;:&quot;https://thediaryofaplayboy.substack.com/subscribe?&quot;,&quot;text&quot;:&quot;Subscribe&quot;,&quot;language&quot;:&quot;en&quot;}" data-component-name="SubscribeWidgetToDOM"><div class="subscription-widget show-subscribe"><div class="preamble"><p class="cta-caption">The Diary of a Playboy is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.</p></div><form class="subscription-widget-subscribe"><input type="email" class="email-input" name="email" placeholder="Type your email&#8230;" tabindex="-1"><input type="submit" class="button primary" value="Subscribe"><div class="fake-input-wrapper"><div class="fake-input"></div><div class="fake-button"></div></div></form></div></div>]]></content:encoded></item><item><title><![CDATA[When Intimacy Becomes Ammunition]]></title><description><![CDATA[How to Recover from a Bitter Divorce]]></description><link>https://thediaryofaplayboy.substack.com/p/when-intimacy-becomes-ammunition</link><guid isPermaLink="false">https://thediaryofaplayboy.substack.com/p/when-intimacy-becomes-ammunition</guid><dc:creator><![CDATA[Martins Itua]]></dc:creator><pubDate>Wed, 02 Sep 2026 21:15:59 GMT</pubDate><enclosure url="iframe.php?url=https%3A%2F%2Fsubstackcdn.com%2Fimage%2Ffetch%2F%24s_%21bUBI%21%2Cf_auto%2Cq_auto%3Agood%2Cfl_progressive%3Asteep%2Fhttps%253A%252F%252Fsubstack-post-media.s3.amazonaws.com%252Fpublic%252Fimages%252Fd3664794-c5d2-481d-a6c2-9b99411f3972_320x480.jpeg" length="0" type="image/jpeg"/><content:encoded><![CDATA[<p>There is something particularly cruel about a bitter divorce.</p><p>The person fighting you is not a stranger.</p><div class="subscription-widget-wrap-editor" data-attrs="{&quot;url&quot;:&quot;https://thediaryofaplayboy.substack.com/subscribe?&quot;,&quot;text&quot;:&quot;Subscribe&quot;,&quot;language&quot;:&quot;en&quot;}" data-component-name="SubscribeWidgetToDOM"><div class="subscription-widget show-subscribe"><div class="preamble"><p class="cta-caption">The Diary of a Playboy is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.</p></div><form class="subscription-widget-subscribe"><input type="email" class="email-input" name="email" placeholder="Type your email&#8230;" tabindex="-1"><input type="submit" class="button primary" value="Subscribe"><div class="fake-input-wrapper"><div class="fake-input"></div><div class="fake-button"></div></div></form></div></div><p>They know you.</p><p>They know what frightens you. They know your insecurities, your mistakes, your family, your finances, your weaknesses. They know what happens to you when the bedroom door closes.</p><p>Once, you gave them that knowledge because you felt safe.</p><p>Now some of it may be used against you.</p><p>And perhaps that is what makes a bitter divorce so different from an ordinary conflict. The person standing on the other side once stood beside you.</p><p>You shared a bed.</p><p>You made plans.</p><p>You laughed together.</p><p>You may have created children together.</p><p>At some point, one of you probably looked at the other and genuinely believed:</p><p><em>I want to spend the rest of my life with you.</em></p><p>Then somehow, <em>I love you</em> becomes <em>I hate you.</em></p><p><em>I will protect you</em> becomes <em>I will expose you.</em></p><p>And in the darkest cases, two people who once believed they could not live without each other can reach a place where they seem determined to destroy each other.</p><p>How does that happen?</p><p>Where exactly does love end and war begin?</p><p><strong>How does love travel that far?</strong></p><p>How does the person whose secrets you once protected become someone whose destruction you can contemplate?</p><p>That is when intimacy becomes ammunition.</p><p>But here is the danger.</p><p>Long after the lawyers leave, the papers are signed and everyone else moves on, you can remain at war.</p><p>You can divorce someone legally and remain emotionally married to them for years through anger, revenge and the need to be vindicated.</p><p>So perhaps recovering from a bitter divorce begins with understanding how two people who once loved each other became enemies in the first place.</p><div class="captioned-image-container"><figure><a class="image-link image2 is-viewable-img" target="_blank" href="iframe.php?url=https%3A%2F%2Fsubstackcdn.com%2Fimage%2Ffetch%2F%24s_%21bUBI%21%2Cf_auto%2Cq_auto%3Agood%2Cfl_progressive%3Asteep%2Fhttps%253A%252F%252Fsubstack-post-media.s3.amazonaws.com%252Fpublic%252Fimages%252Fd3664794-c5d2-481d-a6c2-9b99411f3972_320x480.jpeg" data-component-name="Image2ToDOM"><div class="image2-inset"><picture><source type="image/webp" 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srcset="https://substackcdn.com/image/fetch/$s_!bUBI!,w_424,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fd3664794-c5d2-481d-a6c2-9b99411f3972_320x480.jpeg 424w, https://substackcdn.com/image/fetch/$s_!bUBI!,w_848,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fd3664794-c5d2-481d-a6c2-9b99411f3972_320x480.jpeg 848w, https://substackcdn.com/image/fetch/$s_!bUBI!,w_1272,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fd3664794-c5d2-481d-a6c2-9b99411f3972_320x480.jpeg 1272w, https://substackcdn.com/image/fetch/$s_!bUBI!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fd3664794-c5d2-481d-a6c2-9b99411f3972_320x480.jpeg 1456w" sizes="auto, 100vw" loading="lazy"></picture><div class="image-link-expand"><div class="pencraft pc-display-flex pc-gap-8 pc-reset"><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container restack-image buttonBase-GK1x3M"><svg aria-hidden="true" width="20" height="20" viewBox="0 0 20 20" fill="none" stroke-width="1.5" stroke="var(--color-fg-primary)" stroke-linecap="round" stroke-linejoin="round" xmlns="http://www.w3.org/2000/svg" class="icon-noB79L"><g><path d="M2.53001 7.81595C3.49179 4.73911 6.43281 2.5 9.91173 2.5C13.1684 2.5 15.9537 4.46214 17.0852 7.23684L17.6179 8.67647M17.6179 8.67647L18.5002 4.26471M17.6179 8.67647L13.6473 6.91176M17.4995 12.1841C16.5378 15.2609 13.5967 17.5 10.1178 17.5C6.86118 17.5 4.07589 15.5379 2.94432 12.7632L2.41165 11.3235M2.41165 11.3235L1.5293 15.7353M2.41165 11.3235L6.38224 13.0882"></path></g></svg></button><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container view-image buttonBase-GK1x3M"><svg xmlns="http://www.w3.org/2000/svg" width="20" height="20" viewBox="0 0 24 24" fill="none" stroke="currentColor" stroke-width="2" stroke-linecap="round" stroke-linejoin="round" class="lucide lucide-maximize2 lucide-maximize-2 icon-noB79L"><polyline points="15 3 21 3 21 9"></polyline><polyline points="9 21 3 21 3 15"></polyline><line x1="21" x2="14" y1="3" y2="10"></line><line x1="3" x2="10" y1="21" y2="14"></line></svg></button></div></div></div></a></figure></div><h2><span data-color="#ff0000" style="color: rgb(255, 0, 0);">When Love Turns Into War</span></h2><p>Perhaps one of the strangest things about divorce is how quickly the language can change.</p><p>The person who once called you <em>baby</em> now refers to you through a lawyer.</p><p>The home you built together becomes an asset.</p><p>The children become the subject of negotiations.</p><p>Money becomes leverage.</p><p>Old messages become evidence.</p><p>Private conversations are replayed for strangers.</p><p>And sometimes the bedroom itself enters the courtroom.</p><p>Few modern divorces illustrate the ugliness of this transformation more vividly than the relationship between Johnny Depp and Amber Heard.</p><p>They married in February 2015. Heard filed for divorce in May 2016, after roughly fifteen months of marriage, and the divorce was finalised in January 2017.</p><p>But the marriage did not really end there.</p><p>What followed became a years-long public war involving competing allegations of abuse, lawsuits and eventually the extraordinary 2022 defamation trial in Virginia.</p><p>Millions of people watched as the private remains of a marriage were laid out in public.</p><p>Recordings of arguments were played.</p><p>Text messages were examined.</p><p>Photographs were produced.</p><p>Friends, employees, doctors and former partners became witnesses.</p><p>And some of the most intimate and disturbing allegations about what supposedly happened between two people behind closed doors were discussed before lawyers, cameras and a global audience.</p><p>Whatever anyone believes about Depp or Heard, and both made serious allegations against the other, something about the spectacle was profoundly sad.</p><p>These were once two people in love.</p><p>There were wedding photographs.</p><p>There was attraction.</p><p>There must have been tenderness.</p><p>There were private jokes, private conversations and private moments that belonged only to them.</p><p>Then somehow, the private world they had created together became evidence.</p><p>That is what a bitter divorce can do.</p><p><strong>Intimacy becomes ammunition.</strong></p><p>And perhaps strangers can never hurt us with quite the same precision as former lovers because strangers were never given the map.</p><p>Your spouse knows where you are insecure.</p><p>They know what embarrasses you.</p><p>They know what happened in your childhood.</p><p>They know the mistake you made ten years ago.</p><p>They know what you said when you were frightened, drunk, angry, naked, vulnerable or ashamed.</p><p>Love gave them access.</p><p>Bitterness can give them a reason to use it.</p><p>But how does someone who once protected your vulnerabilities become willing to expose them?</p><p>There is rarely a switch.</p><p>There is an accumulation.</p><p>Hurt becomes resentment.</p><p>Resentment becomes contempt.</p><p>And contempt does something particularly dangerous: it begins rewriting history.</p><p>The person no longer thinks, <em>We had something beautiful and then something terrible happened to us.</em></p><p>They begin thinking, <em>You were always terrible. I simply didn&#8217;t see it.</em></p><p>Suddenly every memory is reinterpreted.</p><p>Every kindness had an ulterior motive.</p><p>Every disagreement becomes evidence.</p><p>Every past mistake becomes part of the prosecution.</p><p>The wedding photographs have not changed. The honeymoon still happened. The laughter was real. The tenderness was real.</p><p>But bitterness edits the archive.</p><p>Eventually, you stop seeing the person you once loved.</p><p>You see an enemy.</p><p>And enemies are treated differently.</p><p>You want the house.</p><p>You want the children.</p><p>You want the money.</p><p>You want their friends to know what they did.</p><p>You want their family to know who they &#8220;really&#8221; are.</p><p>You want their new relationship to fail.</p><p>You want them embarrassed.</p><p>Sometimes you want them ruined.</p><p>And in the darkest divorces, <em>I cannot imagine my life without you</em> somehow becomes <em>I wish you were no longer in it at all.</em></p><p>That is the frightening transformation.</p><p>But there is something even more important to understand.</p><p><strong>Hatred can keep two people connected almost as powerfully as love.</strong></p><p>You may have stopped sleeping beside them. You may live in different houses. You may have divided the property and signed every document.</p><p>Yet if their happiness still angers you, their new relationship consumes you, their name changes your mood and you still organise part of your life around proving that they were wrong, the war continues.</p><p>The marriage may be dead.</p><p>But the attachment is not.</p><p>And that is why the first step in recovering from a bitter divorce may be one of the hardest:</p><p><strong>You have to stop trying to win a marriage that is already over.</strong></p><div class="captioned-image-container"><figure><a class="image-link image2 is-viewable-img" target="_blank" href="iframe.php?url=https%3A%2F%2Fsubstackcdn.com%2Fimage%2Ffetch%2F%24s_%21iBu4%21%2Cf_auto%2Cq_auto%3Agood%2Cfl_progressive%3Asteep%2Fhttps%253A%252F%252Fsubstack-post-media.s3.amazonaws.com%252Fpublic%252Fimages%252F132a9637-8dae-4c78-8e56-7d4ccc24ebe7_870x653.jpeg" data-component-name="Image2ToDOM"><div class="image2-inset"><picture><source type="image/webp" srcset="https://substackcdn.com/image/fetch/$s_!iBu4!,w_424,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F132a9637-8dae-4c78-8e56-7d4ccc24ebe7_870x653.jpeg 424w, https://substackcdn.com/image/fetch/$s_!iBu4!,w_848,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F132a9637-8dae-4c78-8e56-7d4ccc24ebe7_870x653.jpeg 848w, https://substackcdn.com/image/fetch/$s_!iBu4!,w_1272,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F132a9637-8dae-4c78-8e56-7d4ccc24ebe7_870x653.jpeg 1272w, https://substackcdn.com/image/fetch/$s_!iBu4!,w_1456,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F132a9637-8dae-4c78-8e56-7d4ccc24ebe7_870x653.jpeg 1456w" sizes="auto, 100vw"><img src="iframe.php?url=https%3A%2F%2Fsubstackcdn.com%2Fimage%2Ffetch%2F%24s_%21iBu4%21%2Cw_1456%2Cc_limit%2Cf_auto%2Cq_auto%3Agood%2Cfl_progressive%3Asteep%2Fhttps%253A%252F%252Fsubstack-post-media.s3.amazonaws.com%252Fpublic%252Fimages%252F132a9637-8dae-4c78-8e56-7d4ccc24ebe7_870x653.jpeg" width="870" height="653" data-attrs="{&quot;src&quot;:&quot;https://substack-post-media.s3.amazonaws.com/public/images/132a9637-8dae-4c78-8e56-7d4ccc24ebe7_870x653.jpeg&quot;,&quot;srcNoWatermark&quot;:null,&quot;fullscreen&quot;:null,&quot;imageSize&quot;:null,&quot;height&quot;:653,&quot;width&quot;:870,&quot;resizeWidth&quot;:null,&quot;bytes&quot;:65198,&quot;alt&quot;:null,&quot;title&quot;:null,&quot;type&quot;:&quot;image/jpeg&quot;,&quot;href&quot;:null,&quot;belowTheFold&quot;:true,&quot;topImage&quot;:false,&quot;internalRedirect&quot;:&quot;https://thediaryofaplayboy.substack.com/i/213920727?img=https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F132a9637-8dae-4c78-8e56-7d4ccc24ebe7_870x653.jpeg&quot;,&quot;isProcessing&quot;:false,&quot;align&quot;:null,&quot;offset&quot;:false}" class="sizing-normal" alt="" srcset="https://substackcdn.com/image/fetch/$s_!iBu4!,w_424,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F132a9637-8dae-4c78-8e56-7d4ccc24ebe7_870x653.jpeg 424w, https://substackcdn.com/image/fetch/$s_!iBu4!,w_848,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F132a9637-8dae-4c78-8e56-7d4ccc24ebe7_870x653.jpeg 848w, https://substackcdn.com/image/fetch/$s_!iBu4!,w_1272,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F132a9637-8dae-4c78-8e56-7d4ccc24ebe7_870x653.jpeg 1272w, https://substackcdn.com/image/fetch/$s_!iBu4!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F132a9637-8dae-4c78-8e56-7d4ccc24ebe7_870x653.jpeg 1456w" sizes="auto, 100vw" loading="lazy"></picture><div class="image-link-expand"><div class="pencraft pc-display-flex pc-gap-8 pc-reset"><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container restack-image buttonBase-GK1x3M"><svg aria-hidden="true" width="20" height="20" viewBox="0 0 20 20" fill="none" stroke-width="1.5" stroke="var(--color-fg-primary)" stroke-linecap="round" stroke-linejoin="round" xmlns="http://www.w3.org/2000/svg" class="icon-noB79L"><g><path d="M2.53001 7.81595C3.49179 4.73911 6.43281 2.5 9.91173 2.5C13.1684 2.5 15.9537 4.46214 17.0852 7.23684L17.6179 8.67647M17.6179 8.67647L18.5002 4.26471M17.6179 8.67647L13.6473 6.91176M17.4995 12.1841C16.5378 15.2609 13.5967 17.5 10.1178 17.5C6.86118 17.5 4.07589 15.5379 2.94432 12.7632L2.41165 11.3235M2.41165 11.3235L1.5293 15.7353M2.41165 11.3235L6.38224 13.0882"></path></g></svg></button><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container view-image buttonBase-GK1x3M"><svg xmlns="http://www.w3.org/2000/svg" width="20" height="20" viewBox="0 0 24 24" fill="none" stroke="currentColor" stroke-width="2" stroke-linecap="round" stroke-linejoin="round" class="lucide lucide-maximize2 lucide-maximize-2 icon-noB79L"><polyline points="15 3 21 3 21 9"></polyline><polyline points="9 21 3 21 3 15"></polyline><line x1="21" x2="14" y1="3" y2="10"></line><line x1="3" x2="10" y1="21" y2="14"></line></svg></button></div></div></div></a></figure></div><p>One of the hardest things to surrender after a bitter divorce is not the marriage.</p><p>It is the need to win.</p><p>You want the truth acknowledged.</p><p>You want the people who heard their version of the story to hear yours.</p><p>You want the person who betrayed you to admit what they did.</p><p>You want the children, the family, the friends, perhaps even the world, to understand that you were not the villain.</p><p>And somewhere beneath all of that may be an even quieter desire.</p><p>You want your former spouse to regret losing you.</p><p>This is understandable.</p><p>When someone has hurt you deeply, justice can feel like part of healing.</p><p>But there is a difference between seeking justice where it is necessary and building your emotional recovery around vindication.</p><p>Because what happens if the apology never comes?</p><p>What if they never admit what they did?</p><p>What if the people who believed their version never change their minds?</p><p>What if, most painfully, the person who made your life miserable appears to move on and become perfectly happy?</p><p>Do you postpone your own peace until life punishes them?</p><p>That is the trap.</p><p>A bitter divorce can end the marriage while creating a new relationship between two people: <strong>the relationship of enemies.</strong></p><p>You are still watching each other.</p><p>Still reacting to each other.</p><p>Still discussing each other.</p><p>Still making decisions partly because of each other.</p><p>Love has disappeared, but emotional dependence remains.</p><p>And revenge can be strangely intimate.</p><p>The opposite of love is not always hatred. Hatred still requires attention. It still gives another person space inside your head.</p><p>Perhaps the real opposite of love is the day they simply stop having that power.</p><p>This does not mean pretending nothing happened.</p><p>It does not mean surrendering legitimate financial claims, abandoning your children, tolerating abuse or refusing to defend yourself when necessary.</p><p>It means understanding that there are battles you may need to fight without allowing the war to become your identity.</p><p>Your former spouse does not have to lose for you to recover.</p><p>They do not have to become miserable.</p><p>Their new relationship does not have to collapse.</p><p>They do not even have to understand what they did to you.</p><p>At some point, you have to decide that <strong>your peace will no longer require their participation.</strong></p><p>And that may be the first time since the divorce began that you truly start taking your life back.</p><div class="captioned-image-container"><figure><a class="image-link image2 is-viewable-img" target="_blank" href="iframe.php?url=https%3A%2F%2Fsubstackcdn.com%2Fimage%2Ffetch%2F%24s_%21DMSS%21%2Cf_auto%2Cq_auto%3Agood%2Cfl_progressive%3Asteep%2Fhttps%253A%252F%252Fsubstack-post-media.s3.amazonaws.com%252Fpublic%252Fimages%252F82cae4d3-614d-4650-9a8e-4d84821b47a8_512x320.jpeg" data-component-name="Image2ToDOM"><div class="image2-inset"><picture><source type="image/webp" srcset="https://substackcdn.com/image/fetch/$s_!DMSS!,w_424,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F82cae4d3-614d-4650-9a8e-4d84821b47a8_512x320.jpeg 424w, https://substackcdn.com/image/fetch/$s_!DMSS!,w_848,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F82cae4d3-614d-4650-9a8e-4d84821b47a8_512x320.jpeg 848w, https://substackcdn.com/image/fetch/$s_!DMSS!,w_1272,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F82cae4d3-614d-4650-9a8e-4d84821b47a8_512x320.jpeg 1272w, https://substackcdn.com/image/fetch/$s_!DMSS!,w_1456,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F82cae4d3-614d-4650-9a8e-4d84821b47a8_512x320.jpeg 1456w" sizes="auto, 100vw"><img src="iframe.php?url=https%3A%2F%2Fsubstackcdn.com%2Fimage%2Ffetch%2F%24s_%21DMSS%21%2Cw_1456%2Cc_limit%2Cf_auto%2Cq_auto%3Agood%2Cfl_progressive%3Asteep%2Fhttps%253A%252F%252Fsubstack-post-media.s3.amazonaws.com%252Fpublic%252Fimages%252F82cae4d3-614d-4650-9a8e-4d84821b47a8_512x320.jpeg" width="512" height="320" 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srcset="https://substackcdn.com/image/fetch/$s_!DMSS!,w_424,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F82cae4d3-614d-4650-9a8e-4d84821b47a8_512x320.jpeg 424w, https://substackcdn.com/image/fetch/$s_!DMSS!,w_848,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F82cae4d3-614d-4650-9a8e-4d84821b47a8_512x320.jpeg 848w, https://substackcdn.com/image/fetch/$s_!DMSS!,w_1272,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F82cae4d3-614d-4650-9a8e-4d84821b47a8_512x320.jpeg 1272w, https://substackcdn.com/image/fetch/$s_!DMSS!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F82cae4d3-614d-4650-9a8e-4d84821b47a8_512x320.jpeg 1456w" sizes="auto, 100vw" loading="lazy"></picture><div class="image-link-expand"><div class="pencraft pc-display-flex pc-gap-8 pc-reset"><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container restack-image buttonBase-GK1x3M"><svg aria-hidden="true" width="20" height="20" viewBox="0 0 20 20" fill="none" stroke-width="1.5" stroke="var(--color-fg-primary)" stroke-linecap="round" stroke-linejoin="round" xmlns="http://www.w3.org/2000/svg" class="icon-noB79L"><g><path d="M2.53001 7.81595C3.49179 4.73911 6.43281 2.5 9.91173 2.5C13.1684 2.5 15.9537 4.46214 17.0852 7.23684L17.6179 8.67647M17.6179 8.67647L18.5002 4.26471M17.6179 8.67647L13.6473 6.91176M17.4995 12.1841C16.5378 15.2609 13.5967 17.5 10.1178 17.5C6.86118 17.5 4.07589 15.5379 2.94432 12.7632L2.41165 11.3235M2.41165 11.3235L1.5293 15.7353M2.41165 11.3235L6.38224 13.0882"></path></g></svg></button><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container view-image buttonBase-GK1x3M"><svg xmlns="http://www.w3.org/2000/svg" width="20" height="20" viewBox="0 0 24 24" fill="none" stroke="currentColor" stroke-width="2" stroke-linecap="round" stroke-linejoin="round" class="lucide lucide-maximize2 lucide-maximize-2 icon-noB79L"><polyline points="15 3 21 3 21 9"></polyline><polyline points="9 21 3 21 3 15"></polyline><line x1="21" x2="14" y1="3" y2="10"></line><line x1="3" x2="10" y1="21" y2="14"></line></svg></button></div></div></div></a></figure></div><h2><span data-color="#ff00ff" style="color: rgb(255, 0, 255);">Take Back the Person the Divorce Took From You</span></h2><p>There is another loss in divorce that receives far less attention.</p><p>You don&#8217;t only lose a spouse.</p><p>Sometimes you lose yourself.</p><p>For years, you were someone&#8217;s husband or wife. Your routines were intertwined. Your friends overlapped. Your weekends had a rhythm. Your plans for five or ten years from now contained another person.</p><p>Then suddenly there is an empty space where an entire future used to be.</p><p>After a bitter divorce, that emptiness can become dangerous because anger gives you something to put inside it.</p><p>The court case gives you purpose.</p><p>The arguments give you adrenaline.</p><p>Talking about what happened gives you a story.</p><p>Even hatred gives you somewhere to direct your emotions.</p><p>Then one day the fighting stops.</p><p>And you are left with yourself.</p><p>Who are you now?</p><p>That question can be more frightening than the divorce itself.</p><p>Some people answer it by finding another relationship immediately. Someone new desires them, and suddenly they feel attractive again. Wanted again. Chosen again.</p><p>Others bury themselves in work, alcohol, sex, religion, social media or endless self improvement.</p><p>Anything to avoid sitting quietly with the ruins.</p><p>But recovery requires something less dramatic.</p><p>You have to meet yourself again.</p><p>Not the person you were before the marriage. That person may no longer exist.</p><p>And not the bitter version created by the divorce.</p><p>Someone new.</p><p>This is also where honesty becomes uncomfortable.</p><p>Perhaps your former spouse behaved terribly.</p><p>Perhaps you were betrayed, humiliated or treated unfairly.</p><p>But being wronged does not mean there is nothing about yourself worth examining.</p><p>Maybe you ignored warning signs because you were afraid of being alone.</p><p>Maybe you stopped communicating.</p><p>Maybe you became controlling.</p><p>Maybe you tolerated what should never have been tolerated.</p><p>Maybe you retaliated when you should have walked away.</p><p>Maybe you chose the wrong person for reasons you still do not fully understand.</p><p>Looking at those things does not excuse what was done to you.</p><p>It does something more important.</p><p>It prevents your former spouse from becoming the author of everything that happens next.</p><p>Because if the only lesson you take from the marriage is <em>they destroyed it</em>, you may leave the divorce with your innocence intact but your patterns untouched.</p><p>And untouched patterns have a habit of finding new people.</p><p>That may be one of the greatest dangers after a bitter divorce.</p><p>You can change the face without changing the story.</p><p>So don&#8217;t rush to prove that somebody else can love you.</p><p>Don&#8217;t make your next partner responsible for repairing what your former partner broke.</p><p>Don&#8217;t turn every disagreement into evidence that history is repeating itself.</p><p>And don&#8217;t punish someone new for crimes committed by someone who is no longer there.</p><p>Take your time.</p><p>Learn what the marriage revealed about you.</p><p>Recover friendships.</p><p>Return to abandoned interests.</p><p>Rebuild your relationship with your children if the war damaged it.</p><p>Learn to enjoy an empty room without interpreting it as loneliness.</p><p>And perhaps most importantly, rediscover a future that does not require anyone else&#8217;s regret.</p><p>Because eventually recovery arrives at one final question:</p><p><strong>How will you know when you are truly free?</strong></p><p>Perhaps it is not when you forgive them.</p><p>Perhaps you never will.</p><p>It is not when you forget what happened. Some things should not be forgotten.</p><p>And it is certainly not when you convince yourself that the marriage meant nothing. If it meant nothing, it could never have hurt this much.</p><p>Maybe freedom is much quieter.</p><p>One day, someone mentions their name and your body does not react.</p><p>You hear that they are doing well and don&#8217;t feel defeated.</p><p>You discover they have found someone else and don&#8217;t need that relationship to fail.</p><p>You stop checking.</p><p>Stop explaining.</p><p>Stop rehearsing the argument you would finally win if only you had one more opportunity to have it.</p><p>You no longer need an apology.</p><p>You no longer need witnesses.</p><p>You no longer need them to regret losing you.</p><p>And perhaps, most importantly, you stop allowing the worst thing that happened in your marriage to become the most important thing about the rest of your life.</p><p>That is recovery.</p><p>Not forgetting.</p><p>Not pretending.</p><p>Not necessarily forgiving.</p><p>Just freedom.</p><p>Because the real tragedy of a bitter divorce is not that two people who once loved each other can eventually become enemies.</p><p>It is that they can remain enemies long after there is anything left to fight about.</p><p>At some point, somebody has to put down the weapon.</p><p>Let it be you.</p><p>Not because they deserve your mercy.</p><p>Because <strong>you deserve your life back.</strong></p><p>The lawyers may have ended your marriage months or even years ago.</p><p>But there is one final divorce no court can grant you.</p><p><strong>The divorce between your future and your past.</strong></p><p>Sign those papers yourself.</p><p>Thank you for reading.</p><p>If you&#8217;re new here, welcome to <em>The Diary of a Playboy</em>, where we have honest conversations about love, relationships, heartbreak, identity and the complicated business of being human.</p><p>And to those who have been here for a while, thank you for continuing to read, share and bring your own experiences into these conversations.</p><p>I&#8217;d like to leave you with one question:</p><p><strong><span data-color="#ff5600" style="color: rgb(255, 86, 0);">When does a divorce truly end: when the marriage is legally dissolved, or when the other person no longer has the power to disturb your peace?</span></strong></p><p>Until next time, protect your peace, but never let what someone did to you determine who you become.</p><p><strong>Martins Itua</strong></p><div class="subscription-widget-wrap-editor" data-attrs="{&quot;url&quot;:&quot;https://thediaryofaplayboy.substack.com/subscribe?&quot;,&quot;text&quot;:&quot;Subscribe&quot;,&quot;language&quot;:&quot;en&quot;}" data-component-name="SubscribeWidgetToDOM"><div class="subscription-widget show-subscribe"><div class="preamble"><p class="cta-caption">The Diary of a Playboy is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.</p></div><form class="subscription-widget-subscribe"><input type="email" class="email-input" name="email" placeholder="Type your email&#8230;" tabindex="-1"><input type="submit" class="button primary" value="Subscribe"><div class="fake-input-wrapper"><div class="fake-input"></div><div class="fake-button"></div></div></form></div></div>]]></content:encoded></item><item><title><![CDATA[What If Love Doesn't Need a Future?]]></title><description><![CDATA[We have been taught that love must be going somewhere.]]></description><link>https://thediaryofaplayboy.substack.com/p/what-if-love-doesnt-need-a-future</link><guid isPermaLink="false">https://thediaryofaplayboy.substack.com/p/what-if-love-doesnt-need-a-future</guid><dc:creator><![CDATA[Martins Itua]]></dc:creator><pubDate>Mon, 17 Aug 2026 17:58:19 GMT</pubDate><enclosure url="iframe.php?url=https%3A%2F%2Fsubstackcdn.com%2Fimage%2Ffetch%2F%24s_%21iBEU%21%2Cf_auto%2Cq_auto%3Agood%2Cfl_progressive%3Asteep%2Fhttps%253A%252F%252Fsubstack-post-media.s3.amazonaws.com%252Fpublic%252Fimages%252Fa9dfdcb9-43c2-48b8-8b2f-5c924b2de2ba_1024x1536.png" length="0" type="image/jpeg"/><content:encoded><![CDATA[<p>We have been taught that love must be going somewhere.</p><p>You meet.</p><div class="subscription-widget-wrap-editor" data-attrs="{&quot;url&quot;:&quot;https://thediaryofaplayboy.substack.com/subscribe?&quot;,&quot;text&quot;:&quot;Subscribe&quot;,&quot;language&quot;:&quot;en&quot;}" data-component-name="SubscribeWidgetToDOM"><div class="subscription-widget show-subscribe"><div class="preamble"><p class="cta-caption">The Diary of a Playboy is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.</p></div><form class="subscription-widget-subscribe"><input type="email" class="email-input" name="email" placeholder="Type your email&#8230;" tabindex="-1"><input type="submit" class="button primary" value="Subscribe"><div class="fake-input-wrapper"><div class="fake-input"></div><div class="fake-button"></div></div></form></div></div><p>You talk.</p><p>You begin looking forward to hearing from each other.</p><p>Something shifts.</p><p>The conversations become longer. The goodbyes become harder. You start noticing the little things. How they laugh. What makes them angry. How they take their coffee. The silence they make when something is wrong.</p><p>And somewhere along the way, without anyone announcing it, this person begins to matter.</p><p>Then come the questions.</p><p><em>What are we?</em></p><p><em>Where is this going?</em></p><p><em>Do you see a future with me?</em></p><p>Perfectly reasonable questions.</p><p>Because most of us were raised on a particular idea of love.</p><p>Love should progress.</p><p>Dating should become commitment.</p><p>Commitment should become marriage.</p><p>Marriage should become forever.</p><p>That is the script.</p><p>And when a beautiful connection refuses to follow it, we become uncomfortable.</p><p>We need to name it.</p><p>Define it.</p><p>Secure it.</p><p>Move it forward.</p><p>Otherwise, we begin to wonder whether we are wasting our time.</p><p>But lately, I have been wondering whether our obsession with where love is going sometimes prevents us from experiencing where love actually is.</p><p>Think about your own life for a moment.</p><p>There may be someone you once loved who was never really yours.</p><p>Perhaps the timing was wrong.</p><p>Perhaps one of you lived thousands of miles away.</p><p>Perhaps you wanted different lives.</p><p>Perhaps you were wonderful together but would have been terrible at building a life together.</p><p>Perhaps there was extraordinary chemistry and terrible compatibility.</p><p>Or perhaps there was no dramatic reason at all.</p><p>Life simply happened.</p><p>And yet, years later, when their name occasionally crosses your mind, you don&#8217;t necessarily feel regret.</p><p>You smile.</p><p>Because whatever it was, it was real.</p><p>Maybe it lasted three months.</p><p>Maybe three years.</p><p>Maybe it never became an official relationship at all.</p><p>But something happened between you that changed the way you understood love, desire, intimacy or even yourself.</p><p>So what do we call that?</p><p>A failed relationship?</p><p>An almost?</p><p>A mistake?</p><p>A waste of time?</p><p>Or could it simply have been a love story that was complete without becoming permanent?</p><p>We are very good at measuring relationships by duration.</p><p>Twenty years sounds more successful than two.</p><p>Marriage sounds more meaningful than an affair of the heart that never acquired a title.</p><p>Forever sounds more legitimate than <em>for now</em>.</p><p>But time is a strange way to measure meaning.</p><p>Some people can spend decades together and barely touch each other&#8217;s souls.</p><p>Someone else can walk into your life for a season and leave fingerprints on parts of you that remain long after they are gone.</p><p>Maybe permanence and significance were never the same thing.</p><p>And maybe one of the hardest lessons in love is accepting that someone can matter enormously without being meant to remain.</p><p>That thought makes many of us uncomfortable.</p><p>It should.</p><p>Because there is another side to this conversation.</p><p>Sometimes <em>living in the moment</em> is wisdom.</p><p>Sometimes it is simply what we call avoidance when we don&#8217;t want to admit that we are afraid of commitment.</p><p>Sometimes two people genuinely understand what they are sharing and ask nothing more of it.</p><p>And sometimes one person is enjoying the present while the other is quietly waiting for the future.</p><p>Those are not the same thing.</p><p>There is a difference between accepting a relationship for what it is and accepting less than you want because you are hoping it will eventually become more.</p><p>That difference may be where this entire conversation begins.</p><p>Because perhaps the question is not simply whether love needs a future.</p><p>Perhaps the harder question is this:</p><p><strong>Can we love something deeply without needing to own its tomorrow?</strong></p><div class="captioned-image-container"><figure><a class="image-link image2 is-viewable-img" target="_blank" href="iframe.php?url=https%3A%2F%2Fsubstackcdn.com%2Fimage%2Ffetch%2F%24s_%21iBEU%21%2Cf_auto%2Cq_auto%3Agood%2Cfl_progressive%3Asteep%2Fhttps%253A%252F%252Fsubstack-post-media.s3.amazonaws.com%252Fpublic%252Fimages%252Fa9dfdcb9-43c2-48b8-8b2f-5c924b2de2ba_1024x1536.png" data-component-name="Image2ToDOM"><div class="image2-inset"><picture><source type="image/webp" srcset="https://substackcdn.com/image/fetch/$s_!iBEU!,w_424,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fa9dfdcb9-43c2-48b8-8b2f-5c924b2de2ba_1024x1536.png 424w, https://substackcdn.com/image/fetch/$s_!iBEU!,w_848,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fa9dfdcb9-43c2-48b8-8b2f-5c924b2de2ba_1024x1536.png 848w, https://substackcdn.com/image/fetch/$s_!iBEU!,w_1272,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fa9dfdcb9-43c2-48b8-8b2f-5c924b2de2ba_1024x1536.png 1272w, https://substackcdn.com/image/fetch/$s_!iBEU!,w_1456,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fa9dfdcb9-43c2-48b8-8b2f-5c924b2de2ba_1024x1536.png 1456w" sizes="auto, 100vw"><img src="iframe.php?url=https%3A%2F%2Fsubstackcdn.com%2Fimage%2Ffetch%2F%24s_%21iBEU%21%2Cw_1456%2Cc_limit%2Cf_auto%2Cq_auto%3Agood%2Cfl_progressive%3Asteep%2Fhttps%253A%252F%252Fsubstack-post-media.s3.amazonaws.com%252Fpublic%252Fimages%252Fa9dfdcb9-43c2-48b8-8b2f-5c924b2de2ba_1024x1536.png" width="1024" height="1536" 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srcset="https://substackcdn.com/image/fetch/$s_!iBEU!,w_424,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fa9dfdcb9-43c2-48b8-8b2f-5c924b2de2ba_1024x1536.png 424w, https://substackcdn.com/image/fetch/$s_!iBEU!,w_848,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fa9dfdcb9-43c2-48b8-8b2f-5c924b2de2ba_1024x1536.png 848w, https://substackcdn.com/image/fetch/$s_!iBEU!,w_1272,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fa9dfdcb9-43c2-48b8-8b2f-5c924b2de2ba_1024x1536.png 1272w, https://substackcdn.com/image/fetch/$s_!iBEU!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fa9dfdcb9-43c2-48b8-8b2f-5c924b2de2ba_1024x1536.png 1456w" sizes="auto, 100vw" loading="lazy"></picture><div class="image-link-expand"><div class="pencraft pc-display-flex pc-gap-8 pc-reset"><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container restack-image buttonBase-GK1x3M"><svg aria-hidden="true" width="20" height="20" viewBox="0 0 20 20" fill="none" stroke-width="1.5" stroke="var(--color-fg-primary)" stroke-linecap="round" stroke-linejoin="round" xmlns="http://www.w3.org/2000/svg" class="icon-noB79L"><g><path d="M2.53001 7.81595C3.49179 4.73911 6.43281 2.5 9.91173 2.5C13.1684 2.5 15.9537 4.46214 17.0852 7.23684L17.6179 8.67647M17.6179 8.67647L18.5002 4.26471M17.6179 8.67647L13.6473 6.91176M17.4995 12.1841C16.5378 15.2609 13.5967 17.5 10.1178 17.5C6.86118 17.5 4.07589 15.5379 2.94432 12.7632L2.41165 11.3235M2.41165 11.3235L1.5293 15.7353M2.41165 11.3235L6.38224 13.0882"></path></g></svg></button><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container view-image buttonBase-GK1x3M"><svg xmlns="http://www.w3.org/2000/svg" width="20" height="20" viewBox="0 0 24 24" fill="none" stroke="currentColor" stroke-width="2" stroke-linecap="round" stroke-linejoin="round" class="lucide lucide-maximize2 lucide-maximize-2 icon-noB79L"><polyline points="15 3 21 3 21 9"></polyline><polyline points="9 21 3 21 3 15"></polyline><line x1="21" x2="14" y1="3" y2="10"></line><line x1="3" x2="10" y1="21" y2="14"></line></svg></button></div></div></div></a></figure></div><h2>The Tyranny of Forever</h2><p>Perhaps our problem is not love.</p><p>Perhaps it is what we have been taught love is supposed to prove.</p><p>From childhood, almost every great love story we encounter is moving towards something.</p><p>The kiss.</p><p>The proposal.</p><p>The wedding.</p><p>The happily ever after.</p><p>Even the language we use reveals our expectations.</p><p>We say a relationship <em>worked</em> if two people stayed together.</p><p>We say it <em>failed</em> if they separated.</p><p>We congratulate longevity almost automatically, as though duration itself is evidence of love.</p><p>But is it?</p><p>We all know couples who have remained together for decades and stopped truly seeing each other years ago.</p><p>They share a house.</p><p>Children.</p><p>Bills.</p><p>History.</p><p>Perhaps even a bed.</p><p>But very little intimacy.</p><p>And we call that relationship successful because nobody left.</p><p>Meanwhile, two people can meet, love each other honestly, change each other&#8217;s lives, share something extraordinary, and eventually realise that their paths must separate.</p><p>We call that a failed relationship.</p><p>Something about that arithmetic has never quite made sense to me.</p><p>Why should the ending determine the value of everything that came before it?</p><p>A friendship does not become meaningless because someone moves to another country.</p><p>A beautiful holiday is not ruined because eventually we have to come home.</p><p>We don&#8217;t refuse to watch a sunset because we know darkness will follow.</p><p>Yet with romantic love, permanence has somehow become the proof that the experience was real.</p><p>Maybe that is because love frightens us.</p><p>To love someone is to become vulnerable to losing them.</p><p>And permanence offers us the comforting illusion that perhaps we won&#8217;t.</p><p>So we make promises.</p><p>We define relationships.</p><p>We exchange rings.</p><p>We merge homes.</p><p>We build routines.</p><p>None of these things are wrong. Commitment can be one of the most beautiful expressions of love.</p><p>But commitment and possession are not the same thing.</p><p>And sometimes, without realising it, our desire for commitment becomes a desire for certainty.</p><p><em>Tell me you will always be here.</em></p><p><em>Tell me you will never change.</em></p><p><em>Tell me you will always feel this way.</em></p><p><em>Tell me there will never be anyone else.</em></p><p>What we are really asking is:</p><p><em>Tell me I am safe from losing you.</em></p><p>But nobody can honestly promise us that.</p><p>People change.</p><p>Circumstances change.</p><p>Desire changes.</p><p>Life intervenes.</p><p>People die.</p><p>People leave.</p><p>People grow in directions nobody anticipated.</p><p>Sometimes love survives those changes.</p><p>Sometimes it doesn&#8217;t.</p><p>That does not necessarily mean the love was fraudulent.</p><p>Perhaps it means it was human.</p><p>And this is where things become uncomfortable.</p><p>Because if we accept that love does not require permanence to have meaning, we must also accept that some of the most important people in our lives may never become <em>ours</em> in the way we once imagined.</p><p>There is probably someone like that in your story.</p><p>The person you met too early.</p><p>Or too late.</p><p>The person who understood you beautifully but wanted a completely different life.</p><p>The person you could talk to until morning but could never quite build a morning routine with.</p><p>The chemistry was effortless.</p><p>Reality was not.</p><p>Perhaps you tried.</p><p>Perhaps you never did.</p><p>Perhaps circumstances made the decision for you.</p><p>And perhaps, if you are completely honest, you occasionally wonder what might have happened if life had arranged itself differently.</p><p>We tend to call these people <em>the ones that got away</em>.</p><p>But I wonder whether that phrase gets it wrong.</p><p>Maybe they didn&#8217;t get away.</p><p>Maybe they came as far into our lives as they were ever supposed to come.</p><p>Maybe their purpose was not to stay.</p><p>Maybe they were there to awaken something.</p><p>To teach us tenderness.</p><p>To show us desire.</p><p>To expose a wound.</p><p>To remind us who we were before life made us cautious.</p><p>To introduce us to a version of ourselves we had never met before.</p><p>And then to leave.</p><p>That sounds romantic.</p><p>Perhaps dangerously so.</p><p>Because this is exactly where beautiful philosophy can become a convenient excuse for emotional cowardice.</p><p>There are people who speak eloquently about freedom because commitment terrifies them.</p><p>People who celebrate <em>living in the moment</em> because tomorrow would require responsibility.</p><p>People who call something casual while enjoying all the emotional privileges of something serious.</p><p>People who say, <em>Let&#8217;s not put labels on this</em>, when what they really mean is, <em>I want access to you without accountability to you.</em></p><p>And there are people on the other side who agree to these arrangements while secretly hoping patience will eventually turn ambiguity into commitment.</p><p>They say they are enjoying the moment.</p><p>But they are counting the moments.</p><p>Waiting.</p><p>Interpreting.</p><p>Hoping.</p><p>Every intimate weekend becomes evidence.</p><p>Every affectionate message becomes possibility.</p><p>Every goodbye carries the silent question:</p><p><em>When will you finally choose me?</em></p><p>That is not freedom.</p><p>That is emotional waiting disguised as acceptance.</p><p>And perhaps this is where we need to make an important distinction.</p><p>A relationship without a future can still be beautiful.</p><p>A relationship without honesty rarely is.</p><p>Two people can choose something temporary.</p><p>Two people can choose distance.</p><p>Two people can choose intimacy without building a conventional life together.</p><p>Two people can even love each other and recognise that love alone is not enough reason to become permanent partners.</p><p>But both people must be standing inside the same truth.</p><p>Because the moment one person is living in the present while the other is secretly negotiating for a future, what looks like freedom from the outside can become heartbreak on the inside.</p><p>Perhaps that is the real price of loving without demanding forever.</p><p>Not detachment.</p><p>Not indifference.</p><p>Not pretending you don&#8217;t care.</p><p>Honesty.</p><p>The courage to say:</p><p><em>This is what I feel.</em></p><p><em>This is what I want.</em></p><p><em>This is what I can give.</em></p><p><em>And this is what I cannot promise.</em></p><p>Then allowing the other person to decide whether what exists between you is enough.</p><p>Because sometimes love asks us to stay.</p><p>Sometimes it asks us to leave.</p><p>And sometimes, perhaps most painfully, it asks us to stop demanding that something beautiful become something it was never capable of being.</p><h2>The People We Never Quite Forget</h2><p>There are people we get over.</p><p>And then there are people we simply learn to remember differently.</p><p>They no longer occupy our days.</p><p>We don&#8217;t wait for their messages.</p><p>We don&#8217;t check their social media.</p><p>We don&#8217;t secretly imagine them appearing at the door.</p><p>We may have loved other people since.</p><p>Built lives.</p><p>Married.</p><p>Had children.</p><p>Moved countries.</p><p>Become almost unrecognisable from the person they once knew.</p><p>And yet, every now and then, something brings them back.</p><p>A song.</p><p>A city.</p><p>A particular perfume.</p><p>An old photograph.</p><p>A sentence someone says in exactly the way they used to say it.</p><p>And for a few seconds, an entire period of your life returns.</p><p>Not necessarily because you want the person back.</p><p>That distinction matters.</p><p>Sometimes we don&#8217;t miss the person.</p><p>We miss who we were when we knew them.</p><p>There are people who become attached to versions of ourselves that no longer exist.</p><p>The reckless twenty three year old.</p><p>The woman who still believed love could solve everything.</p><p>The man before the divorce.</p><p>The girl before life taught her to protect herself.</p><p>The version of you who could board a plane because someone said, <em>I miss you.</em></p><p>Perhaps that is why certain people remain so difficult to forget.</p><p>Memory does not preserve relationships accurately.</p><p>It edits.</p><p>It softens.</p><p>It selects.</p><p>It keeps the hotel room and forgets the argument at the airport.</p><p>It remembers the midnight conversation and loses the three days of silence that followed.</p><p>It remembers how someone looked at you across a table and conveniently forgets why you eventually stopped sitting at that table.</p><p>Time can be a very generous editor.</p><p>And the relationships that never became ordinary are particularly vulnerable to this kind of romantic editing.</p><p>Because reality never had enough time to interfere.</p><p>You never discovered how they behaved when money became tight.</p><p>You never argued about whose turn it was to take the rubbish out.</p><p>You never had to decide whose family you would visit at Christmas.</p><p>You never watched desire compete with exhaustion, children, mortgages, illness, ageing and Tuesday morning traffic.</p><p>You experienced each other in concentrated doses.</p><p>Dinner.</p><p>Wine.</p><p>Airports.</p><p>Hotels.</p><p>Long conversations.</p><p>Weekends stolen from ordinary life.</p><p>Goodbyes that made everything feel more important because time was always running out.</p><p>Of course it felt extraordinary.</p><p>It never had to survive Tuesday.</p><p>And Tuesday is where many love stories discover what they are actually made of.</p><p>This is why we should be careful when romanticising the person we never quite had.</p><p>Sometimes the relationship remains perfect precisely because life never had the opportunity to make it imperfect.</p><p>The unanswered question becomes more seductive than the answer might ever have been.</p><p><em>What if?</em></p><p>What if we had lived in the same city?</p><p>What if I had met her five years later?</p><p>What if he had been ready?</p><p>What if I had stayed?</p><p>What if neither of us had been married?</p><p>What if I had said yes?</p><p>What if I had not been so afraid?</p><p>There is no argument against <em>what if</em> because it exists in a world where nothing ever goes wrong.</p><p>Reality cannot compete with a life that happened only in imagination.</p><p>But perhaps we don&#8217;t need to destroy those memories either.</p><p>Perhaps maturity is being able to hold two truths at once.</p><p>It was beautiful.</p><p>And it probably would not have worked.</p><p>I loved them.</p><p>And I don&#8217;t want them back.</p><p>They changed me.</p><p>And I am grateful they left.</p><p>What happened mattered.</p><p>And it did not need to become more.</p><p>That last truth may be the hardest.</p><p>Because we have been conditioned to believe that if something mattered enough, we should have fought harder to keep it.</p><p>But keeping someone is not always the highest expression of love.</p><p>Sometimes letting the story remain where it belongs is kinder than dragging it into a future that would eventually destroy what made it beautiful.</p><p>Not every extraordinary connection is an instruction to build a life together.</p><p>Chemistry is not compatibility.</p><p>Desire is not destiny.</p><p>Being understood is not the same as being able to build.</p><p>And love, however powerful, does not automatically make two lives fit.</p><p>Perhaps some people enter our lives simply to show us a room inside ourselves we didn&#8217;t know existed.</p><p>They open the door.</p><p>We walk in.</p><p>Something changes.</p><p>And long after they are gone, the room remains.</p><p>That does not make them the love of our life.</p><p>It does not mean our current partner is somehow less important.</p><p>It does not mean we chose incorrectly.</p><p>It simply means human beings leave traces in one another.</p><p>We are, in part, collections of everyone we have genuinely loved.</p><p>A phrase we still use.</p><p>A song we learned to appreciate.</p><p>A city we now understand differently.</p><p>A confidence someone gave us.</p><p>A wound someone forced us to heal.</p><p>A tenderness we discovered because someone once handled us gently.</p><p>A boundary we developed because someone didn&#8217;t.</p><p>They leave.</p><p>Something stays.</p><p>And perhaps that is enough.</p><p>But there is another question we cannot avoid.</p><p>If someone from your past still occupies a private room inside you, what happens when you build a future with somebody else?</p><p>Because there is a difference between remembering an old love and continuing to live emotionally inside it.</p><p>There is a difference between gratitude and longing.</p><p>Between memory and comparison.</p><p>Between occasionally wondering <em>what if</em> and quietly measuring everyone you meet against someone who exists now mostly in your imagination.</p><p>At some point, honouring what was must also mean allowing it to be over.</p><p>Otherwise, the person who never became your future can begin stealing from the person who actually did.</p><p>And that would turn a beautiful memory into something much less beautiful.</p><p>Perhaps the real art is not forgetting.</p><p>It is knowing where to place the memory.</p><p>Some people belong in our lives.</p><p>Some belong in our past.</p><p>And some belong in that strange, tender place between gratitude and goodbye.</p><p>You don&#8217;t have to erase them.</p><p>You just have to stop waiting for them.</p><h2>Can Love Without a Future Actually Work?</h2><p>So let us come back to the uncomfortable question.</p><p>Can two people genuinely care for each other, desire each other, share intimacy, perhaps even love each other, and still knowingly choose not to build a future together?</p><p>I think they can.</p><p>But it is much harder than the romantic version makes it sound.</p><p>Because human beings have a troublesome habit.</p><p>We become attached.</p><p>We tell ourselves we are enjoying the moment.</p><p>Then the moments accumulate.</p><p>A weekend becomes a routine.</p><p>A good morning text becomes expected.</p><p>A casual phone call becomes the person you instinctively reach for when something happens.</p><p>You begin knowing each other&#8217;s moods.</p><p>Friends know the name.</p><p>Birthdays begin to matter.</p><p>Jealousy appears where supposedly there were no expectations.</p><p>And somewhere along the way, something that required nothing begins quietly asking for something.</p><p>This is where honesty becomes everything.</p><p>Not the honesty we offer the other person.</p><p>The harder kind.</p><p>Honesty with ourselves.</p><p>Because it is remarkably easy to say, <em>I&#8217;m fine with this</em>, when what we really mean is, <em>I&#8217;m hoping this changes.</em></p><p>Easy to say, <em>Let&#8217;s just enjoy what we have</em>, while secretly imagining the day they finally realise they cannot live without us.</p><p>Easy to pretend we don&#8217;t need commitment because asking for it might risk losing the little intimacy we already have.</p><p>That is not freedom.</p><p>That is fear negotiating.</p><p>And no arrangement, however sophisticated its language, can protect us from what we refuse to admit to ourselves.</p><p>If you want more, you want more.</p><p>There is no shame in that.</p><p>Wanting commitment does not make you needy.</p><p>Wanting marriage does not make you old fashioned.</p><p>Wanting exclusivity does not make you insecure.</p><p>Wanting someone to choose you clearly does not mean you are incapable of living in the present.</p><p>Your desires are allowed to have names.</p><p>The danger begins when we abandon them just to remain close to someone who cannot meet them.</p><p>Because there is a difference between choosing a love without a future and accepting one because it is the only version of that person available to you.</p><p>One is freedom.</p><p>The other can become self abandonment.</p><p>And perhaps this is why the word <em>situationship</em> carries so much emotional baggage.</p><p>The problem is rarely the absence of a label.</p><p>The problem is often the presence of unequal hope.</p><p>One person thinks:</p><p><em>This is beautiful.</em></p><p>The other thinks:</p><p><em>This is becoming something.</em></p><p>One person is experiencing.</p><p>The other is investing.</p><p>One person leaves the weekend satisfied.</p><p>The other leaves wondering when the weekends will become a life.</p><p>That imbalance eventually sends an invoice.</p><p>And somebody always pays it.</p><p>So perhaps love without a future can work only when neither person has been deceived, including by themselves.</p><p>Both people know what this is.</p><p>Both know what it is not.</p><p>Both are free to leave.</p><p>Neither is quietly auditioning for promotion.</p><p>Neither is using intimacy to purchase commitment.</p><p>Neither is withholding the truth because the truth might end the arrangement.</p><p>And both understand something else that is rarely discussed.</p><p>The agreement may change.</p><p>Human beings are not contracts.</p><p>You can begin wanting nothing more and discover six months later that you have fallen deeply in love.</p><p>You can believe you are capable of keeping something casual and wake one morning realising that casual left the room months ago.</p><p>You can promise yourself not to become attached and then discover that your heart never signed the agreement.</p><p>What happens then?</p><p>You tell the truth.</p><p>Even if the truth ruins everything.</p><p>Especially then.</p><p>You say:</p><p><em>This no longer works for me.</em></p><p>Or:</p><p><em>I have started wanting something you cannot give me.</em></p><p>Or perhaps:</p><p><em>I thought I could do this without needing a future. I was wrong.</em></p><p>There is enormous dignity in that admission.</p><p>Far more than pretending to be unaffected while quietly breaking.</p><p>Because the purpose of emotional maturity is not to become so detached that nobody can hurt you.</p><p>It is to become honest enough to recognise when something that once brought you joy has begun costing you your peace.</p><p>And then there is commitment itself.</p><p>I don&#8217;t want to romanticise temporary love so much that permanence begins to look unimaginative.</p><p>There is extraordinary beauty in staying.</p><p>In knowing someone beyond flattering lighting.</p><p>In discovering their irritating habits and loving them anyway.</p><p>In surviving Tuesday.</p><p>In raising children.</p><p>In nursing someone through illness.</p><p>In watching bodies change.</p><p>In forgiving.</p><p>In rebuilding.</p><p>In waking beside the same person after twenty years and still reaching for their hand.</p><p>There is romance in airports and stolen weekends.</p><p>But there is also romance in remembering someone&#8217;s prescription.</p><p>In knowing exactly how they like their tea.</p><p>In sitting beside them in a hospital waiting room.</p><p>In arguing about money and still choosing to solve the problem together.</p><p>In carrying each other through the years when neither of you is particularly interesting or easy to love.</p><p>Perhaps forever is not overrated.</p><p>Perhaps we have simply made the mistake of believing it is the only form in which love can be meaningful.</p><p>Temporary love and enduring love are not competing philosophies.</p><p>They ask different things of us.</p><p>One may teach us how to experience.</p><p>The other teaches us how to remain.</p><p>One asks us to release expectation.</p><p>The other asks us to honour commitment.</p><p>Both can be beautiful.</p><p>Both can also become destructive.</p><p>A temporary relationship becomes destructive when someone secretly wants permanence.</p><p>A permanent relationship becomes destructive when people remain long after love, dignity and respect have disappeared simply because leaving would mean admitting that forever ended.</p><p>So maybe duration was never the real question.</p><p>Truth is.</p><p>Are you telling the truth about what you want?</p><p>Are they telling the truth about what they can give?</p><p>Are you staying because this relationship genuinely nourishes you?</p><p>Or because you are afraid there will be nothing after it?</p><p>Are you enjoying the present?</p><p>Or enduring it in exchange for an imagined future?</p><p>And perhaps the most difficult question of all:</p><p>If you knew with absolute certainty that this person would never become your husband, your wife, your permanent partner, would you still choose what you have with them today?</p><p>Your answer may tell you everything.</p><p>Because love does not always need a future.</p><p>But you should never have to sacrifice your own future just to keep love alive in the present.</p><h2>Perhaps Love Doesn&#8217;t Always Need Forever</h2><p>Maybe we have been asking love to do too much.</p><p>To arrive at the right time.</p><p>To choose the right person.</p><p>To survive every season.</p><p>To become commitment.</p><p>To become marriage.</p><p>To become forever.</p><p>And when it doesn&#8217;t, we look back and wonder whether we made a mistake.</p><p>Perhaps we didn&#8217;t.</p><p>Perhaps some people really do come into our lives for a season.</p><p>Not because the love was incomplete.</p><p>Not because someone failed.</p><p>Not because we weren&#8217;t good enough to make them stay.</p><p>But because not everything beautiful is meant to be permanent.</p><p>There are people I have known whom I would never want back in my life, yet I would never wish away the time I had with them.</p><p>That distinction has taken me years to understand.</p><p>You can be grateful for someone and still be glad they are gone.</p><p>You can remember a love tenderly without wanting to resurrect it.</p><p>You can acknowledge that someone changed you without believing they were supposed to stay and enjoy the person you have become.</p><p>And you can love again without betraying what came before.</p><p>Perhaps that is what maturity eventually teaches us.</p><p>We don&#8217;t have to turn every ending into regret.</p><p>We don&#8217;t have to make villains out of everyone who could not stay.</p><p>We don&#8217;t have to diminish what was beautiful simply because it eventually ended.</p><p>Some relationships give us companionship.</p><p>Some give us lessons.</p><p>Some give us wounds.</p><p>Some give us memories.</p><p>And occasionally, someone gives us a glimpse of ourselves we might never have discovered without them.</p><p>Then life moves.</p><p>As it always does.</p><p>The question is whether we move with it.</p><p>Because there is something deeply sad about sacrificing the love available to us today because we are still emotionally negotiating with yesterday.</p><p>Remember them.</p><p>Smile if the memory deserves a smile.</p><p>Cry if there is still something left to grieve.</p><p>Be grateful for whatever was real.</p><p>But know when to close the door.</p><p>And if you are fortunate enough to find someone with whom you genuinely want tomorrow, don&#8217;t become so sophisticated about impermanence that you become afraid to stay.</p><p>Choose them.</p><p>Build.</p><p>Commit.</p><p>Survive Tuesday together.</p><p>There is courage in letting go.</p><p>But there is courage in staying too.</p><p>So, what if love doesn&#8217;t need a future?</p><p>Perhaps sometimes it doesn&#8217;t.</p><p>Perhaps sometimes the moment was the whole story.</p><p>Perhaps the conversation was enough.</p><p>The summer was enough.</p><p>The three years were enough.</p><p>The person was enough.</p><p>Perhaps something can end without having failed.</p><p>But love does need truth.</p><p>Truth about what we feel.</p><p>Truth about what we want.</p><p>Truth about what we can give.</p><p>Truth about when we should stay.</p><p>And truth about when it is time to leave.</p><p>Maybe the measure of a love story should never have been how long it lasted.</p><p>Maybe it should be whether, while it existed, we were honest enough to love without pretending, brave enough to stay when staying was right, and wise enough to leave when leaving became necessary.</p><p>Some people will walk beside us for the rest of our lives.</p><p>Others will walk with us only long enough to change the direction in which we are travelling.</p><p>Both can matter.</p><p>Both can be love.</p><p>And neither needs to be regretted simply because one of them ended.</p><p>Perhaps forever was never the only proof that love was real.</p><p>Thank you for staying with me through this conversation.</p><p>If you&#8217;re new here, welcome. And to those of you who have been here for a while, reading, commenting, sharing your stories and sometimes quietly disagreeing with me, thank you for continuing to make these conversations richer.</p><p>I&#8217;d love to hear what you think.</p><p><strong>Can a love be complete even when it has no future?</strong></p><p>Until next time, keep loving, keep living, and perhaps, sometimes, let a beautiful moment be enough.</p><p><strong>Martins Itua</strong></p><div class="subscription-widget-wrap-editor" data-attrs="{&quot;url&quot;:&quot;https://thediaryofaplayboy.substack.com/subscribe?&quot;,&quot;text&quot;:&quot;Subscribe&quot;,&quot;language&quot;:&quot;en&quot;}" data-component-name="SubscribeWidgetToDOM"><div class="subscription-widget show-subscribe"><div class="preamble"><p class="cta-caption">The Diary of a Playboy is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.</p></div><form class="subscription-widget-subscribe"><input type="email" class="email-input" name="email" placeholder="Type your email&#8230;" tabindex="-1"><input type="submit" class="button primary" value="Subscribe"><div class="fake-input-wrapper"><div class="fake-input"></div><div class="fake-button"></div></div></form></div></div>]]></content:encoded></item><item><title><![CDATA[Why Does Cheating Hit Men So Hard?]]></title><description><![CDATA[There are some things we write and move on from.]]></description><link>https://thediaryofaplayboy.substack.com/p/why-does-cheating-hit-men-so-hard-64c</link><guid isPermaLink="false">https://thediaryofaplayboy.substack.com/p/why-does-cheating-hit-men-so-hard-64c</guid><dc:creator><![CDATA[Martins Itua]]></dc:creator><pubDate>Sat, 15 Aug 2026 17:13:03 GMT</pubDate><enclosure url="iframe.php?url=https%3A%2F%2Fsubstackcdn.com%2Fimage%2Ffetch%2F%24s_%21zJpi%21%2Cw_256%2Cc_limit%2Cf_auto%2Cq_auto%3Agood%2Cfl_progressive%3Asteep%2Fhttps%253A%252F%252Fsubstack-post-media.s3.amazonaws.com%252Fpublic%252Fimages%252F3bc0642f-a38f-4158-a45e-047c9a73c998_1024x1024.png" length="0" type="image/jpeg"/><content:encoded><![CDATA[<p>There are some things we write and move on from.</p><p>And there are others that stay with us because the question was never really settled.</p><div class="subscription-widget-wrap-editor" data-attrs="{&quot;url&quot;:&quot;https://thediaryofaplayboy.substack.com/subscribe?&quot;,&quot;text&quot;:&quot;Subscribe&quot;,&quot;language&quot;:&quot;en&quot;}" data-component-name="SubscribeWidgetToDOM"><div class="subscription-widget show-subscribe"><div class="preamble"><p class="cta-caption">The Diary of a Playboy is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.</p></div><form class="subscription-widget-subscribe"><input type="email" class="email-input" name="email" placeholder="Type your email&#8230;" tabindex="-1"><input type="submit" class="button primary" value="Subscribe"><div class="fake-input-wrapper"><div class="fake-input"></div><div class="fake-button"></div></div></form></div></div><p>I wrote <strong>Why Does Cheating Hit Men So Hard?</strong> in February after watching a video of a man discover his wife with another man.</p><p>But what stayed with me wasn&#8217;t only the betrayal.</p><p>It was what happened afterwards.</p><p>People mocked him for crying.</p><p>They called him weak.</p><p>They said a real man would have walked away without showing emotion.</p><p>And it made me wonder how we arrived at a place where a man can have his heart broken and still be expected to perform strength for everyone watching.</p><p>We tell men to love.</p><p>To trust.</p><p>To commit.</p><p>To provide.</p><p>To protect.</p><p>But when the person they finally allow themselves to be vulnerable with betrays that trust, we sometimes deny them the right to fall apart.</p><p>Cheating can hurt anyone. But for many men, betrayal reaches beyond the relationship. It touches pride, identity, masculinity, self-worth and the terrifying question few people admit asking:</p><p><em>Was I not enough?</em></p><p>I wrote about all of this months ago, and I found myself returning to it recently.</p><p>Not because I think there is one answer.</p><p>But because I think it is a conversation worth having again.</p><p>If you have ever been betrayed, loved someone who was, or wondered why some people never completely recover from infidelity, I&#8217;d love you to read this.</p><p>And when you finish, tell me what you think.</p><p><a href="iframe.php?url=https%3A%2F%2Fthediaryofaplayboy.substack.com%2Fp%2Fwhy-does-cheating-hit-men-so-hard%3Fr%3Dhyiy3%26amp%3Butm_campaign%3Dpost%26amp%3Butm_medium%3Dweb">WHY DOES CHEATING HIT MEN SO HARD? </a></p><p><strong>Martins Itua</strong></p><div class="subscription-widget-wrap-editor" data-attrs="{&quot;url&quot;:&quot;https://thediaryofaplayboy.substack.com/subscribe?&quot;,&quot;text&quot;:&quot;Subscribe&quot;,&quot;language&quot;:&quot;en&quot;}" data-component-name="SubscribeWidgetToDOM"><div class="subscription-widget show-subscribe"><div class="preamble"><p class="cta-caption">The Diary of a Playboy is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.</p></div><form class="subscription-widget-subscribe"><input type="email" class="email-input" name="email" placeholder="Type your email&#8230;" tabindex="-1"><input type="submit" class="button primary" value="Subscribe"><div class="fake-input-wrapper"><div class="fake-input"></div><div class="fake-button"></div></div></form></div></div>]]></content:encoded></item><item><title><![CDATA[The Prologue That Started Everything]]></title><description><![CDATA[Before today&#8217;s article...]]></description><link>https://thediaryofaplayboy.substack.com/p/the-prologue-that-started-everything</link><guid isPermaLink="false">https://thediaryofaplayboy.substack.com/p/the-prologue-that-started-everything</guid><dc:creator><![CDATA[Martins Itua]]></dc:creator><pubDate>Mon, 03 Aug 2026 13:56:56 GMT</pubDate><enclosure url="iframe.php?url=https%3A%2F%2Fsubstackcdn.com%2Fimage%2Ffetch%2F%24s_%213FIF%21%2Cf_auto%2Cq_auto%3Agood%2Cfl_progressive%3Asteep%2Fhttps%253A%252F%252Fsubstack-post-media.s3.amazonaws.com%252Fpublic%252Fimages%252Fc5dd02be-a26d-4399-9060-e07160d09730_1024x1536.png" length="0" type="image/jpeg"/><content:encoded><![CDATA[<h2>Before today&#8217;s article...</h2><p>Every journey has a beginning.</p><p>Not the beginning people celebrate.</p><div class="subscription-widget-wrap-editor" data-attrs="{&quot;url&quot;:&quot;https://thediaryofaplayboy.substack.com/subscribe?&quot;,&quot;text&quot;:&quot;Subscribe&quot;,&quot;language&quot;:&quot;en&quot;}" data-component-name="SubscribeWidgetToDOM"><div class="subscription-widget show-subscribe"><div class="preamble"><p class="cta-caption">The Diary of a Playboy is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.</p></div><form class="subscription-widget-subscribe"><input type="email" class="email-input" name="email" placeholder="Type your email&#8230;" tabindex="-1"><input type="submit" class="button primary" value="Subscribe"><div class="fake-input-wrapper"><div class="fake-input"></div><div class="fake-button"></div></div></form></div></div><p>The quieter one.</p><p>The page written before anyone was watching.</p><p>The words that existed before there were readers, conversations, or a community.</p><p>Long before <em>The Diary of a Playboy</em> became a place where we explored love, heartbreak, grief, identity, family, hope and the strange ways life shapes us, there was only a question.</p><p>A question that refused to leave me alone.</p><p>I sat down to answer it, and what emerged became the prologue to a book.</p><p>Looking back now, I realise I wasn&#8217;t simply writing an introduction.</p><p>I was unknowingly laying the first stone of everything that would follow.</p><p>Every essay I&#8217;ve written since carries traces of what began on those pages.</p><p>The themes are there.</p><p>The voice is there.</p><p>The curiosity is there.</p><p>Even the questions I am still trying to answer today were already beginning to take shape.</p><p>Many of you joined this journey long after those words were written.</p><p>So today, I wanted to do something different.</p><p>I wanted to take you back to the very first page.</p><p>Not because it is perfect.</p><p>But because it is honest.</p><p>Because every story deserves to remember where it began.</p><p>Welcome to the beginning</p><div class="captioned-image-container"><figure><a class="image-link image2 is-viewable-img" target="_blank" href="iframe.php?url=https%3A%2F%2Fsubstackcdn.com%2Fimage%2Ffetch%2F%24s_%213FIF%21%2Cf_auto%2Cq_auto%3Agood%2Cfl_progressive%3Asteep%2Fhttps%253A%252F%252Fsubstack-post-media.s3.amazonaws.com%252Fpublic%252Fimages%252Fc5dd02be-a26d-4399-9060-e07160d09730_1024x1536.png" data-component-name="Image2ToDOM"><div class="image2-inset"><picture><source type="image/webp" srcset="https://substackcdn.com/image/fetch/$s_!3FIF!,w_424,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fc5dd02be-a26d-4399-9060-e07160d09730_1024x1536.png 424w, https://substackcdn.com/image/fetch/$s_!3FIF!,w_848,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fc5dd02be-a26d-4399-9060-e07160d09730_1024x1536.png 848w, https://substackcdn.com/image/fetch/$s_!3FIF!,w_1272,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fc5dd02be-a26d-4399-9060-e07160d09730_1024x1536.png 1272w, https://substackcdn.com/image/fetch/$s_!3FIF!,w_1456,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fc5dd02be-a26d-4399-9060-e07160d09730_1024x1536.png 1456w" sizes="auto, 100vw"><img src="iframe.php?url=https%3A%2F%2Fsubstackcdn.com%2Fimage%2Ffetch%2F%24s_%213FIF%21%2Cw_1456%2Cc_limit%2Cf_auto%2Cq_auto%3Agood%2Cfl_progressive%3Asteep%2Fhttps%253A%252F%252Fsubstack-post-media.s3.amazonaws.com%252Fpublic%252Fimages%252Fc5dd02be-a26d-4399-9060-e07160d09730_1024x1536.png" width="1024" height="1536" 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srcset="https://substackcdn.com/image/fetch/$s_!3FIF!,w_424,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fc5dd02be-a26d-4399-9060-e07160d09730_1024x1536.png 424w, https://substackcdn.com/image/fetch/$s_!3FIF!,w_848,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fc5dd02be-a26d-4399-9060-e07160d09730_1024x1536.png 848w, https://substackcdn.com/image/fetch/$s_!3FIF!,w_1272,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fc5dd02be-a26d-4399-9060-e07160d09730_1024x1536.png 1272w, https://substackcdn.com/image/fetch/$s_!3FIF!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fc5dd02be-a26d-4399-9060-e07160d09730_1024x1536.png 1456w" sizes="auto, 100vw" loading="lazy"></picture><div class="image-link-expand"><div class="pencraft pc-display-flex pc-gap-8 pc-reset"><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container restack-image buttonBase-GK1x3M"><svg aria-hidden="true" width="20" height="20" viewBox="0 0 20 20" fill="none" stroke-width="1.5" stroke="var(--color-fg-primary)" stroke-linecap="round" stroke-linejoin="round" xmlns="http://www.w3.org/2000/svg" class="icon-noB79L"><g><path d="M2.53001 7.81595C3.49179 4.73911 6.43281 2.5 9.91173 2.5C13.1684 2.5 15.9537 4.46214 17.0852 7.23684L17.6179 8.67647M17.6179 8.67647L18.5002 4.26471M17.6179 8.67647L13.6473 6.91176M17.4995 12.1841C16.5378 15.2609 13.5967 17.5 10.1178 17.5C6.86118 17.5 4.07589 15.5379 2.94432 12.7632L2.41165 11.3235M2.41165 11.3235L1.5293 15.7353M2.41165 11.3235L6.38224 13.0882"></path></g></svg></button><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container view-image buttonBase-GK1x3M"><svg xmlns="http://www.w3.org/2000/svg" width="20" height="20" viewBox="0 0 24 24" fill="none" stroke="currentColor" stroke-width="2" stroke-linecap="round" stroke-linejoin="round" class="lucide lucide-maximize2 lucide-maximize-2 icon-noB79L"><polyline points="15 3 21 3 21 9"></polyline><polyline points="9 21 3 21 3 15"></polyline><line x1="21" x2="14" y1="3" y2="10"></line><line x1="3" x2="10" y1="21" y2="14"></line></svg></button></div></div></div></a></figure></div><p><strong><span>PROLOGUE</span></strong></p><p><em><span>Lake Como, Present Day</span></em></p><p><span>They say a man remembers two things as he grows older: the women he loved&#8230; and the lies he told himself to survive.</span></p><p><span>I remember both. Too vividly.</span></p><p><span>My name is Alexander Moretti.<br>Lex, to most.</span></p><p><span>I&#8217;m 47 years old.<br>I own four passports, a dozen tailored suits,<br>a villa that feels more like a memory than a home,<br>and a past I&#8217;ve been running from longer than I care to admit.</span></p><p><span>I&#8217;ve been called a charmer, a bastard, a dream, a mistake. I&#8217;ve been the best night of someone&#8217;s life&#8230; and the ghost that never left their bed.</span></p><p><span>Right now, I&#8217;m sitting at a marble desk in my bedroom overlooking Lake Como, a glass of Amarone in one hand, this pen in the other. It&#8217;s past midnight. The lake is still. And for once, I&#8217;m not pretending.</span></p><p><span>This is the story of a man who had everything.<br>Everything but peace.</span></p><p><span>A week ago, a letter arrived. The kind no one sends anymore; paper, ink, the edges curled like an old scar. The handwriting was jagged, fading.</span></p><p><span>It was from </span><em><span>Elijah Saint</span></em><span>. A jazzman-turned-preacher. The man who once found me face-down in a gutter in New Orleans and dragged me into a church where the only thing louder than my heartbeat was the saxophone bleeding from his hands.</span></p><p><span>His letter was only eight words long.</span></p><p><span>&#8220;Lex, the clock is louder than the music now.&#8221;</span></p><p><span>I read it five times. Then I lit a cigar I was saving for never, poured wine, and pulled out the journal I buried at the bottom of a drawer I hadn&#8217;t opened in ten years.</span></p><p><span>This journal has seen things.<br>Midnight tears. Bloody knuckles. A lipstick stain from a woman whose name I still whisper in my sleep.<br>It&#8217;s where I wrote everything I couldn&#8217;t say out loud.</span></p><p><span>And now, I&#8217;m writing again; not because I want to but because I must.</span></p><p><span>Because when the women are gone and the music fades, you&#8217;re left with nothing but your own voice echoing through the dark. And I can&#8217;t lie to myself anymore. Not here. Not now.</span></p><p><span>You see, people think they know men like me.</span></p><p><span>They think we&#8217;re made of velvet and vice. They see the tailored suits, the smile that lands like a sin, the passport stamped with secrets, and they assume we live in pleasure.</span></p><p><span>They never stop to ask what it cost.</span></p><p><span>They don&#8217;t see the night I stood on a penthouse balcony in Manhattan with my wrists bleeding and my phone on airplane mode.</span></p><p><span>They don&#8217;t know about Mina Liu, the painter from Kyoto who once told me I was the most beautiful kind of hollow she&#8217;d ever seen.</span></p><p><span>They don&#8217;t see Amara, the only woman who ever looked me in the eye and didn&#8217;t flinch. The one I left before she could leave me.</span></p><p><span>They don&#8217;t know what it&#8217;s like to stand in a room filled with 200 people and still feel like you&#8217;re choking on air.</span></p><p><span>I was born in Lagos, the son of a Nigerian oil baron and an Italian opera singer. A fire and a song. My mother left when I was eight. My father was present in the way war is present: loud, unpredictable, and lethal.</span></p><p><span>At ten, I was shipped off to boarding school in Switzerland, where boys with names like Benedict and Sebastian taught me three things: never show weakness, learn how to lie without blinking, and screw before you&#8217;re screwed.</span></p><p><span>By twenty, I was fluent in five languages and broken in six.<br>By twenty-five, I was a whispered legend in Monaco and Milan.</span></p><p><span>They called me </span><em><span>the man who made women forget themselves</span></em><span>.</span></p><p><span>It was never about sex. Not really.<br>It was about being needed.<br>Worshipped. Wanted so badly that they&#8217;d forgive the inevitable ending.</span></p><p><span>Because I always left.<br>Always.</span></p><p><span>And if you&#8217;re reading this expecting redemption, let me save you the trouble: I&#8217;m not writing to be forgiven. I&#8217;m writing because something inside me is cracking. Not a clean break. A slow, splintering fracture, the kind you feel in your bones before a storm.</span></p><p><span>There was a woman once, Sofia Carbone, who whispered in my ear, </span><em><span>&#8220;You don&#8217;t love women, Lex. You collect them.&#8221;</span></em><span><br>And she was right.</span></p><p><span>I collected hearts like watches.<br>Loved them in flashes. Left before dawn.</span></p><p><span>And yet, I can tell you the scent of their necks, the cadence of their laughter, the exact way their eyes closed just before they came undone in my arms.</span></p><p><span>I wasn&#8217;t careless. I was selfish.<br>There&#8217;s a difference.</span></p><p><span>I built an empire on charm, secrets, and expensive wine. I invested in a modelling agency in New York, a club in Dubai, and a vineyard in Tuscany. I watched a man die in my hotel suite in Cartagena. I once paid two million dollars for silence and regretted not paying more.</span></p><p><span>There was a year I don&#8217;t remember.<br>Then there was </span><em><span>her</span></em><span>. The one that cut through the noise.</span></p><p><span>Amara Okonkwo.<br>A name that still makes my chest tighten like a noose.</span></p><p><span>She didn&#8217;t fall for the act. She peeled it off. Slowly. Brutally. Beautifully.<br>And when she saw what was underneath, she stayed.</span></p><p><span>Until I ran.</span></p><p><span>But I&#8217;m getting ahead of myself.<br>This story isn&#8217;t linear. Neither is regret.</span></p><p><span>This is the story of how a man becomes a myth, and how a myth becomes a memory. It&#8217;s the story of choices made in bedrooms, backseats, boardrooms, and airports. Of the moments we think mean nothing&#8230; until they define us.</span></p><p><span>This isn&#8217;t a book. It&#8217;s a confession booth.<br>And you&#8217;re inside with me now.</span></p><p><span>I&#8217;ll tell you about the night Alejandro Serrano and I buried a secret in Barcelona.<br>About the girl in Havana who might be my daughter.<br>About the time I saw my father cry, and wished he hadn&#8217;t.<br>About the lies I told Amara.<br>About the truths I told myself.</span></p><p><span>This journal is a mirror.<br>And I hate what I see in it.</span></p><p><span>But Elijah is right. The clock </span><em><span>is</span></em><span> louder than the music now.<br>And before it stops completely, I want to be naked in the only way that matters.</span></p><p><span>Stripped of glamour.<br>Stripped of seduction.<br>Stripped of the lies.</span></p><p><span>This is the diary of a playboy.<br>And this&#8230; this is how it begins.</span></p><p>Thank you for reading.</p><p>If you&#8217;re new here, welcome to <strong>The Diary of a Playboy</strong>...</p><p>...Until next time,</p><p><strong>Martins Itua</strong></p><div class="subscription-widget-wrap-editor" data-attrs="{&quot;url&quot;:&quot;https://thediaryofaplayboy.substack.com/subscribe?&quot;,&quot;text&quot;:&quot;Subscribe&quot;,&quot;language&quot;:&quot;en&quot;}" data-component-name="SubscribeWidgetToDOM"><div class="subscription-widget show-subscribe"><div class="preamble"><p class="cta-caption">The Diary of a Playboy is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.</p></div><form class="subscription-widget-subscribe"><input type="email" class="email-input" name="email" placeholder="Type your email&#8230;" tabindex="-1"><input type="submit" class="button primary" value="Subscribe"><div class="fake-input-wrapper"><div class="fake-input"></div><div class="fake-button"></div></div></form></div></div>]]></content:encoded></item><item><title><![CDATA[Why Some Families Stay Poor for Generations]]></title><description><![CDATA[Every family passes something down.]]></description><link>https://thediaryofaplayboy.substack.com/p/why-some-families-stay-poor-for-generations</link><guid isPermaLink="false">https://thediaryofaplayboy.substack.com/p/why-some-families-stay-poor-for-generations</guid><dc:creator><![CDATA[Martins Itua]]></dc:creator><pubDate>Tue, 28 Jul 2026 18:27:05 GMT</pubDate><enclosure url="iframe.php?url=https%3A%2F%2Fsubstackcdn.com%2Fimage%2Ffetch%2F%24s_%21ZFyP%21%2Cf_auto%2Cq_auto%3Agood%2Cfl_progressive%3Asteep%2Fhttps%253A%252F%252Fsubstack-post-media.s3.amazonaws.com%252Fpublic%252Fimages%252F376189f6-1ebb-4ca4-8b59-a1b424e05e1c_1024x1536.png" length="0" type="image/jpeg"/><content:encoded><![CDATA[<p>Every family passes something down.</p><p>For some, it is land.</p><div class="subscription-widget-wrap-editor" data-attrs="{&quot;url&quot;:&quot;https://thediaryofaplayboy.substack.com/subscribe?&quot;,&quot;text&quot;:&quot;Subscribe&quot;,&quot;language&quot;:&quot;en&quot;}" data-component-name="SubscribeWidgetToDOM"><div class="subscription-widget show-subscribe"><div class="preamble"><p class="cta-caption">The Diary of a Playboy is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.</p></div><form class="subscription-widget-subscribe"><input type="email" class="email-input" name="email" placeholder="Type your email&#8230;" tabindex="-1"><input type="submit" class="button primary" value="Subscribe"><div class="fake-input-wrapper"><div class="fake-input"></div><div class="fake-button"></div></div></form></div></div><p>For others, it is a thriving business, a respected name, or a network of relationships that quietly opens doors long before an introduction is made.</p><p>Some inherit recipes that become restaurants. Some inherit books that become libraries. Some inherit values that become legacies.</p><p>But there are families that seem to pass down something else.</p><p>Scarcity.</p><p>Generation after generation, they work hard. They wake before sunrise. They sacrifice. They pray. They dream that their children will have the life they never had.</p><p>Yet somehow, when one generation leaves, the next arrives carrying the same burdens.</p><p>The same financial struggles.</p><p>The same fears.</p><p>The same limitations.</p><p>It is as though poverty has become an heirloom, handed from parent to child as faithfully as a family name.</p><p>Why does this happen?</p><p>Is poverty really inherited?</p><p>Or is something else being passed down that we mistake for destiny?</p><p>This is not an article about blaming poor people for being poor. Nor is it an attempt to ignore the realities of corruption, inequality, poor governance, conflict, or the countless structural barriers that trap millions of people despite their best efforts.</p><p>Those realities matter.</p><p>They shape lives in profound ways.</p><p>But they do not tell the whole story.</p><p>Because if they did, no one would ever escape poverty.</p><p>Yet many do.</p><p>And if some families find a way to break the cycle while others remain trapped in it for generations, then perhaps the inheritance we should examine is not simply money.</p><p>Perhaps families pass down beliefs.</p><p>Habits.</p><p>Relationships.</p><p>Expectations.</p><p>Ways of thinking.</p><p>Ways of responding to opportunity.</p><p>Ways of seeing the world.</p><p>Invisible inheritances that shape a person&#8217;s future long before they earn their first salary.</p><p>The greatest inheritance a family leaves behind is rarely found in a will.</p><p>It is found in the way the next generation thinks.</p><p>And perhaps that is where we should begin.</p><div class="captioned-image-container"><figure><a class="image-link image2 is-viewable-img" target="_blank" href="iframe.php?url=https%3A%2F%2Fsubstackcdn.com%2Fimage%2Ffetch%2F%24s_%21ZFyP%21%2Cf_auto%2Cq_auto%3Agood%2Cfl_progressive%3Asteep%2Fhttps%253A%252F%252Fsubstack-post-media.s3.amazonaws.com%252Fpublic%252Fimages%252F376189f6-1ebb-4ca4-8b59-a1b424e05e1c_1024x1536.png" data-component-name="Image2ToDOM"><div class="image2-inset"><picture><source type="image/webp" srcset="https://substackcdn.com/image/fetch/$s_!ZFyP!,w_424,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F376189f6-1ebb-4ca4-8b59-a1b424e05e1c_1024x1536.png 424w, https://substackcdn.com/image/fetch/$s_!ZFyP!,w_848,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F376189f6-1ebb-4ca4-8b59-a1b424e05e1c_1024x1536.png 848w, https://substackcdn.com/image/fetch/$s_!ZFyP!,w_1272,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F376189f6-1ebb-4ca4-8b59-a1b424e05e1c_1024x1536.png 1272w, https://substackcdn.com/image/fetch/$s_!ZFyP!,w_1456,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F376189f6-1ebb-4ca4-8b59-a1b424e05e1c_1024x1536.png 1456w" sizes="auto, 100vw"><img src="iframe.php?url=https%3A%2F%2Fsubstackcdn.com%2Fimage%2Ffetch%2F%24s_%21ZFyP%21%2Cw_1456%2Cc_limit%2Cf_auto%2Cq_auto%3Agood%2Cfl_progressive%3Asteep%2Fhttps%253A%252F%252Fsubstack-post-media.s3.amazonaws.com%252Fpublic%252Fimages%252F376189f6-1ebb-4ca4-8b59-a1b424e05e1c_1024x1536.png" width="1024" height="1536" data-attrs="{&quot;src&quot;:&quot;https://substack-post-media.s3.amazonaws.com/public/images/376189f6-1ebb-4ca4-8b59-a1b424e05e1c_1024x1536.png&quot;,&quot;srcNoWatermark&quot;:null,&quot;fullscreen&quot;:null,&quot;imageSize&quot;:null,&quot;height&quot;:1536,&quot;width&quot;:1024,&quot;resizeWidth&quot;:null,&quot;bytes&quot;:2205490,&quot;alt&quot;:null,&quot;title&quot;:null,&quot;type&quot;:&quot;image/png&quot;,&quot;href&quot;:null,&quot;belowTheFold&quot;:true,&quot;topImage&quot;:false,&quot;internalRedirect&quot;:&quot;https://thediaryofaplayboy.substack.com/i/208867275?img=https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F376189f6-1ebb-4ca4-8b59-a1b424e05e1c_1024x1536.png&quot;,&quot;isProcessing&quot;:false,&quot;align&quot;:null,&quot;offset&quot;:false}" class="sizing-normal" alt="" srcset="https://substackcdn.com/image/fetch/$s_!ZFyP!,w_424,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F376189f6-1ebb-4ca4-8b59-a1b424e05e1c_1024x1536.png 424w, https://substackcdn.com/image/fetch/$s_!ZFyP!,w_848,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F376189f6-1ebb-4ca4-8b59-a1b424e05e1c_1024x1536.png 848w, https://substackcdn.com/image/fetch/$s_!ZFyP!,w_1272,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F376189f6-1ebb-4ca4-8b59-a1b424e05e1c_1024x1536.png 1272w, https://substackcdn.com/image/fetch/$s_!ZFyP!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F376189f6-1ebb-4ca4-8b59-a1b424e05e1c_1024x1536.png 1456w" sizes="auto, 100vw" loading="lazy"></picture><div class="image-link-expand"><div class="pencraft pc-display-flex pc-gap-8 pc-reset"><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container restack-image buttonBase-GK1x3M"><svg aria-hidden="true" width="20" height="20" viewBox="0 0 20 20" fill="none" stroke-width="1.5" stroke="var(--color-fg-primary)" stroke-linecap="round" stroke-linejoin="round" xmlns="http://www.w3.org/2000/svg" class="icon-noB79L"><g><path d="M2.53001 7.81595C3.49179 4.73911 6.43281 2.5 9.91173 2.5C13.1684 2.5 15.9537 4.46214 17.0852 7.23684L17.6179 8.67647M17.6179 8.67647L18.5002 4.26471M17.6179 8.67647L13.6473 6.91176M17.4995 12.1841C16.5378 15.2609 13.5967 17.5 10.1178 17.5C6.86118 17.5 4.07589 15.5379 2.94432 12.7632L2.41165 11.3235M2.41165 11.3235L1.5293 15.7353M2.41165 11.3235L6.38224 13.0882"></path></g></svg></button><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container view-image buttonBase-GK1x3M"><svg xmlns="http://www.w3.org/2000/svg" width="20" height="20" viewBox="0 0 24 24" fill="none" stroke="currentColor" stroke-width="2" stroke-linecap="round" stroke-linejoin="round" class="lucide lucide-maximize2 lucide-maximize-2 icon-noB79L"><polyline points="15 3 21 3 21 9"></polyline><polyline points="9 21 3 21 3 15"></polyline><line x1="21" x2="14" y1="3" y2="10"></line><line x1="3" x2="10" y1="21" y2="14"></line></svg></button></div></div></div></a></figure></div><p>One of the greatest misconceptions about poverty is that it is simply the absence of money.</p><p>If that were true, solving poverty would be relatively straightforward.</p><p>Give people money.</p><p>Yet history tells a far more complicated story.</p><p>People win lotteries and return to bankruptcy.</p><p>Athletes earn millions only to lose everything within a decade.</p><p>Businesses receive grants and still collapse.</p><p>Families inherit wealth and squander it within a generation.</p><p>At the same time, others begin with almost nothing and slowly build fortunes that endure for decades.</p><p>Clearly, money is part of the story.</p><p>But it is not the whole story.</p><p>Poverty is rarely just an economic condition.</p><p>More often, it becomes a way of thinking, a way of making decisions, and eventually, a way of life.</p><p>Over time, it begins to shape how a family sees the world.</p><p>What they believe is possible.</p><p>What they believe people like them can achieve.</p><p>The risks they are willing to take.</p><p>The opportunities they overlook because no one around them has ever taken them before.</p><p>Children absorb these lessons long before anyone sits them down to teach them.</p><p>A child who grows up hearing, <em>&#8220;People like us never get ahead,&#8221;</em> is not simply hearing a sentence.</p><p>They are inheriting a worldview.</p><p>A child who constantly hears that wealthy people are dishonest, that education changes nothing, that success belongs to other families, is being handed an invisible script.</p><p>And invisible scripts often become visible lives.</p><p>That is why two children can grow up in the same neighbourhood, attend the same schools, and yet imagine completely different futures.</p><p>One sees obstacles.</p><p>The other sees possibilities.</p><p>Neither perspective appeared overnight.</p><p>Both were inherited long before they became conscious choices.</p><p>This is why poverty can survive even when circumstances improve.</p><p>A family may move into a bigger house yet continue making decisions from a mindset shaped by generations of scarcity.</p><p>Because escaping poverty is not only about changing your income.</p><p>Sometimes, it requires changing the story your family has been telling itself for generations.</p><p>And perhaps that is the hardest inheritance of all.</p><p><strong>One of the most powerful classrooms a child will ever sit in is not a school.</strong></p><p>It is the dinner table.</p><p>It is the conversations overheard in the living room.</p><p>It is the arguments about money after the children have supposedly gone to bed.</p><p>It is the way parents react when someone in the neighbourhood buys a new car, starts a business or sends a child abroad.</p><p>Children are always listening.</p><p>Long before they understand economics, they understand emotion.</p><p>They notice whether money is always spoken about with fear.</p><p>Whether success is admired or quietly resented.</p><p>Whether education is treated as an investment or merely an obligation.</p><p>Whether every setback becomes someone else&#8217;s fault or an opportunity to learn.</p><p>These conversations become more than memories.</p><p>They become a child&#8217;s operating system.</p><p>Years later, as adults, people believe they are making independent decisions.</p><p>Often, they are simply acting out beliefs they absorbed before they were old enough to question them.</p><p>That is why two people can be presented with the very same opportunity and respond in completely different ways.</p><p>One sees possibility.</p><p>The other sees danger.</p><p>One asks, <em>What if this works?</em></p><p>The other asks, <em>What if I lose everything?</em></p><p>Neither question was born in that moment.</p><p>Both have a history.</p><p><strong>There is something else families pass down.</strong></p><p>Patterns.</p><p>The way they respond to disappointment.</p><p>The way they handle money.</p><p>The way they speak about education.</p><p>The way they react to opportunity.</p><p>The way they solve problems.</p><p>The way they think about tomorrow.</p><p>These things are rarely taught in a formal lesson.</p><p>They are absorbed through observation.</p><p>A child watches how a parent responds when money is scarce.</p><p>They notice whether the response is panic or planning.</p><p>Whether failure becomes an excuse to give up or a lesson to grow.</p><p>Whether success is celebrated or viewed with suspicion.</p><p>Whether reading is a habit or a punishment.</p><p>Whether dreams are encouraged or quietly dismissed as unrealistic.</p><p>None of these moments seem particularly significant on their own.</p><p>But over time, they become patterns.</p><p>And patterns become habits.</p><p>Habits become decisions.</p><p>Decisions become lives.</p><p>This is why breaking the cycle of poverty is about far more than earning a higher income.</p><p>It is about changing the patterns that quietly shaped the generations before you.</p><p>The inheritance that matters most is often invisible.</p><p>And because it is invisible, many families never realize they are passing it on.</p><p><strong>None of this is written to blame our parents or our grandparents.</strong></p><p>Most of them gave us everything they had.</p><p>Many carried burdens we will never fully understand. They worked hard, sacrificed endlessly and hoped their children would have opportunities they never did.</p><p>But they could only pass on what they themselves had received.</p><p>That is true of every generation.</p><p>Which also means every generation has the opportunity to leave a different inheritance.</p><p>Perhaps that is where real change begins.</p><p>Not with a lottery ticket.</p><p>Not with sudden wealth.</p><p>But with one person who decides that the patterns will end with them.</p><p>One person who chooses curiosity over fear.</p><p>Learning over limitation.</p><p>Planning over survival.</p><p>Possibility over resignation.</p><p>Every family passes something down.</p><p>The question is never whether there will be an inheritance.</p><p>The question is what that inheritance will be.</p><p>Money can be lost.</p><p>Property can change hands.</p><p>Businesses can fail.</p><p>But the values, beliefs and habits we pass to the next generation can shape lives long after we are gone.</p><p>Perhaps the greatest gift we can leave our children is not a larger bank account.</p><p>Perhaps it is a larger way of seeing the world.</p><p>Because somewhere in every family tree is the person who changes the direction of the branches.</p><p>Perhaps that person is you.</p><p>Thank you for reading.</p><p>If you&#8217;re new here, welcome to <strong>The Diary of a Playboy</strong>, where we explore the ideas, stories and quiet truths that shape our lives, our relationships and the legacy we leave behind.</p><p>And to those who keep returning, thank you. Your thoughtful comments, reflections and conversations continue to make this more than a newsletter. They make it a community.</p><p>If this article resonated with you, I&#8217;d love to hear your thoughts.</p><p><strong>What is one belief, habit or lesson your family passed down that has shaped your life for better or for worse?</strong></p><p>Leave a comment below. I read every one.</p><p>Until next time,</p><p><strong>Martins Itua</strong></p><div class="subscription-widget-wrap-editor" data-attrs="{&quot;url&quot;:&quot;https://thediaryofaplayboy.substack.com/subscribe?&quot;,&quot;text&quot;:&quot;Subscribe&quot;,&quot;language&quot;:&quot;en&quot;}" data-component-name="SubscribeWidgetToDOM"><div class="subscription-widget show-subscribe"><div class="preamble"><p class="cta-caption">The Diary of a Playboy is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.</p></div><form class="subscription-widget-subscribe"><input type="email" class="email-input" name="email" placeholder="Type your email&#8230;" tabindex="-1"><input type="submit" class="button primary" value="Subscribe"><div class="fake-input-wrapper"><div class="fake-input"></div><div class="fake-button"></div></div></form></div></div>]]></content:encoded></item><item><title><![CDATA[What to Do When the Person You Love Doesn't Love You Back]]></title><description><![CDATA[There are few pains more confusing than loving someone who does not love you the same way.The Diary of a Playboy is a reader-supported publication.]]></description><link>https://thediaryofaplayboy.substack.com/p/what-to-do-when-the-person-you-love</link><guid isPermaLink="false">https://thediaryofaplayboy.substack.com/p/what-to-do-when-the-person-you-love</guid><dc:creator><![CDATA[Martins Itua]]></dc:creator><pubDate>Fri, 10 Jul 2026 17:37:46 GMT</pubDate><enclosure url="iframe.php?url=https%3A%2F%2Fsubstackcdn.com%2Fimage%2Ffetch%2F%24s_%21C7Li%21%2Cf_auto%2Cq_auto%3Agood%2Cfl_progressive%3Asteep%2Fhttps%253A%252F%252Fsubstack-post-media.s3.amazonaws.com%252Fpublic%252Fimages%252Fa275e6d4-b5a9-4813-bd71-8d859efa1049_1024x1536.png" length="0" type="image/jpeg"/><content:encoded><![CDATA[<div class="captioned-image-container"><figure><a class="image-link image2 is-viewable-img" target="_blank" href="iframe.php?url=https%3A%2F%2Fsubstackcdn.com%2Fimage%2Ffetch%2F%24s_%21C7Li%21%2Cf_auto%2Cq_auto%3Agood%2Cfl_progressive%3Asteep%2Fhttps%253A%252F%252Fsubstack-post-media.s3.amazonaws.com%252Fpublic%252Fimages%252Fa275e6d4-b5a9-4813-bd71-8d859efa1049_1024x1536.png" data-component-name="Image2ToDOM"><div class="image2-inset"><picture><source type="image/webp" srcset="https://substackcdn.com/image/fetch/$s_!C7Li!,w_424,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fa275e6d4-b5a9-4813-bd71-8d859efa1049_1024x1536.png 424w, https://substackcdn.com/image/fetch/$s_!C7Li!,w_848,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fa275e6d4-b5a9-4813-bd71-8d859efa1049_1024x1536.png 848w, https://substackcdn.com/image/fetch/$s_!C7Li!,w_1272,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fa275e6d4-b5a9-4813-bd71-8d859efa1049_1024x1536.png 1272w, https://substackcdn.com/image/fetch/$s_!C7Li!,w_1456,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fa275e6d4-b5a9-4813-bd71-8d859efa1049_1024x1536.png 1456w" sizes="100vw"><img src="iframe.php?url=https%3A%2F%2Fsubstackcdn.com%2Fimage%2Ffetch%2F%24s_%21C7Li%21%2Cw_1456%2Cc_limit%2Cf_auto%2Cq_auto%3Agood%2Cfl_progressive%3Asteep%2Fhttps%253A%252F%252Fsubstack-post-media.s3.amazonaws.com%252Fpublic%252Fimages%252Fa275e6d4-b5a9-4813-bd71-8d859efa1049_1024x1536.png" width="1024" height="1536" data-attrs="{&quot;src&quot;:&quot;https://substack-post-media.s3.amazonaws.com/public/images/a275e6d4-b5a9-4813-bd71-8d859efa1049_1024x1536.png&quot;,&quot;srcNoWatermark&quot;:null,&quot;fullscreen&quot;:null,&quot;imageSize&quot;:null,&quot;height&quot;:1536,&quot;width&quot;:1024,&quot;resizeWidth&quot;:null,&quot;bytes&quot;:2284524,&quot;alt&quot;:null,&quot;title&quot;:null,&quot;type&quot;:&quot;image/png&quot;,&quot;href&quot;:null,&quot;belowTheFold&quot;:false,&quot;topImage&quot;:true,&quot;internalRedirect&quot;:&quot;https://thediaryofaplayboy.substack.com/i/206472880?img=https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fa275e6d4-b5a9-4813-bd71-8d859efa1049_1024x1536.png&quot;,&quot;isProcessing&quot;:false,&quot;align&quot;:null,&quot;offset&quot;:false}" class="sizing-normal" alt="" srcset="https://substackcdn.com/image/fetch/$s_!C7Li!,w_424,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fa275e6d4-b5a9-4813-bd71-8d859efa1049_1024x1536.png 424w, https://substackcdn.com/image/fetch/$s_!C7Li!,w_848,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fa275e6d4-b5a9-4813-bd71-8d859efa1049_1024x1536.png 848w, https://substackcdn.com/image/fetch/$s_!C7Li!,w_1272,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fa275e6d4-b5a9-4813-bd71-8d859efa1049_1024x1536.png 1272w, https://substackcdn.com/image/fetch/$s_!C7Li!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fa275e6d4-b5a9-4813-bd71-8d859efa1049_1024x1536.png 1456w" sizes="100vw" fetchpriority="high"></picture><div class="image-link-expand"><div class="pencraft pc-display-flex pc-gap-8 pc-reset"><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container restack-image buttonBase-GK1x3M"><svg aria-hidden="true" width="20" height="20" viewBox="0 0 20 20" fill="none" stroke-width="1.5" stroke="var(--color-fg-primary)" stroke-linecap="round" stroke-linejoin="round" xmlns="http://www.w3.org/2000/svg" class="icon-noB79L"><g><path d="M2.53001 7.81595C3.49179 4.73911 6.43281 2.5 9.91173 2.5C13.1684 2.5 15.9537 4.46214 17.0852 7.23684L17.6179 8.67647M17.6179 8.67647L18.5002 4.26471M17.6179 8.67647L13.6473 6.91176M17.4995 12.1841C16.5378 15.2609 13.5967 17.5 10.1178 17.5C6.86118 17.5 4.07589 15.5379 2.94432 12.7632L2.41165 11.3235M2.41165 11.3235L1.5293 15.7353M2.41165 11.3235L6.38224 13.0882"></path></g></svg></button><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container view-image buttonBase-GK1x3M"><svg xmlns="http://www.w3.org/2000/svg" width="20" height="20" viewBox="0 0 24 24" fill="none" stroke="currentColor" stroke-width="2" stroke-linecap="round" stroke-linejoin="round" class="lucide lucide-maximize2 lucide-maximize-2 icon-noB79L"><polyline points="15 3 21 3 21 9"></polyline><polyline points="9 21 3 21 3 15"></polyline><line x1="21" x2="14" y1="3" y2="10"></line><line x1="3" x2="10" y1="21" y2="14"></line></svg></button></div></div></div></a></figure></div><p></p><p>There are few pains more confusing than loving someone who does not love you the same way.</p><div class="subscription-widget-wrap-editor" data-attrs="{&quot;url&quot;:&quot;https://thediaryofaplayboy.substack.com/subscribe?&quot;,&quot;text&quot;:&quot;Subscribe&quot;,&quot;language&quot;:&quot;en&quot;}" data-component-name="SubscribeWidgetToDOM"><div class="subscription-widget show-subscribe"><div class="preamble"><p class="cta-caption">The Diary of a Playboy is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.</p></div><form class="subscription-widget-subscribe"><input type="email" class="email-input" name="email" placeholder="Type your email&#8230;" tabindex="-1"><input type="submit" class="button primary" value="Subscribe"><div class="fake-input-wrapper"><div class="fake-input"></div><div class="fake-button"></div></div></form></div></div><p>Not because they hate you.</p><p>Not because they wish you harm.</p><p>Simply because their heart has chosen a different direction.</p><p>For many of us, this experience begins long before adulthood.</p><p>A boy who cannot stop thinking about a girl who barely notices he exists.</p><p>A girl who waits endlessly for someone who never calls.</p><p>A university student convinced that if they are patient enough, kind enough, or loving enough, one day they will finally be chosen.</p><p>For some, that pattern never really ends.</p><p>Only the faces change.</p><p>The longing remains.</p><p>If you live long enough, you will almost certainly love someone who cannot love you back.</p><p>That is part of being human.</p><p>The real question is not whether it will happen.</p><p>The real question is what you do when it does.</p><p>Because unrequited love has a way of making us negotiate with reality.</p><p>We tell ourselves they just need more time.</p><p>That if we love harder, they will eventually see us.</p><p>That if we become more successful, more attractive, more patient, or more understanding, something inside them will suddenly change.</p><p>Sometimes it does.</p><p>Most times it doesn&#8217;t.</p><p>And somewhere between hope and denial, we begin to lose something far more important than the relationship we never had.</p><p>We begin to lose ourselves.</p><div class="native-video-embed" data-component-name="VideoPlaceholder" data-attrs="{&quot;mediaUploadId&quot;:&quot;ec090d9a-870f-480d-9c6d-fca8552f4906&quot;,&quot;duration&quot;:null}"></div><p></p><p>I suspect almost everyone reading this has lived some version of this story.</p><p>Perhaps you were the teenager who waited endlessly for someone who never noticed you.</p><p>Perhaps you spent years trying to convince someone to choose you.</p><p>Perhaps you eventually discovered that the person you had been waiting for was never coming, and that the only person you really needed to find again was yourself.</p><p>If that is your story, I&#8217;d love to hear it.</p><p>Not because there is any joy in reopening old wounds, but because someone reading your experience today may find the courage they need to begin healing tomorrow.</p><p>How did you handle unrequited love?</p><p>What did it teach you?</p><p>What advice would you give someone who is struggling to let go of a person who doesn&#8217;t love them back?</p><p>Leave a comment below. If your story is too personal to share publicly, you&#8217;re welcome to send me an email instead.</p><p><em><strong>Sometimes the greatest gift we can give another person is the reminder that they are not alone.</strong></em></p><p>Thank you for reading.</p><p>If you&#8217;re new here, welcome to <strong>The Diary of a Playboy</strong>, where we explore the complexities of life, love, relationships, and the quiet lessons that shape who we become.</p><p>And to everyone who keeps returning, thank you for walking this journey with me. Your thoughts, stories, and reflections continue to make this space richer than I ever imagined.</p><p>Until next time, take care of your heart.</p><p><strong>Martins Itua</strong></p><div class="subscription-widget-wrap-editor" data-attrs="{&quot;url&quot;:&quot;https://thediaryofaplayboy.substack.com/subscribe?&quot;,&quot;text&quot;:&quot;Subscribe&quot;,&quot;language&quot;:&quot;en&quot;}" data-component-name="SubscribeWidgetToDOM"><div class="subscription-widget show-subscribe"><div class="preamble"><p class="cta-caption">The Diary of a Playboy is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.</p></div><form class="subscription-widget-subscribe"><input type="email" class="email-input" name="email" placeholder="Type your email&#8230;" tabindex="-1"><input type="submit" class="button primary" value="Subscribe"><div class="fake-input-wrapper"><div class="fake-input"></div><div class="fake-button"></div></div></form></div></div>]]></content:encoded></item><item><title><![CDATA[How To Have Difficult Conversations in Relationships]]></title><description><![CDATA[A Practical Guide to Saying the Hard Things Without Breaking Trust.]]></description><link>https://thediaryofaplayboy.substack.com/p/how-to-have-difficult-conversations-65a</link><guid isPermaLink="false">https://thediaryofaplayboy.substack.com/p/how-to-have-difficult-conversations-65a</guid><dc:creator><![CDATA[Martins Itua]]></dc:creator><pubDate>Mon, 29 Jun 2026 18:40:51 GMT</pubDate><enclosure url="iframe.php?url=https%3A%2F%2Fapi.substack.com%2Ffeed%2Fpodcast%2F204158191%2F2e7c96174294175ccd0bbff55c6a3a6a.mp3" length="0" type="audio/mpeg"/><content:encoded><![CDATA[<p>Some conversations change relationships forever.</p><p>Others end them before they ever had a chance.</p><p>If you&#8217;ve ever struggled to say the right thing at the right time, or wished a difficult conversation had gone differently, this guide is for you.</p><p>You can get your copy using the payment link below.</p><p><a href="iframe.php?url=https%3A%2F%2Fbuy.stripe.com%2F5kQ7sMgqkdRA5rY5P6e3e00"><span data-color="#ff5600" style="color: rgb(255, 86, 0);">Get the Guide Here</span></a></p><p><strong>Martins Itua</strong></p><p>#thediaryofaplayboy #relationships #communication #marriage #love #meotionalintelligence #conflictresolution #personalgrowth #selfawareness #psychology</p>]]></content:encoded></item><item><title><![CDATA[HOW TO HAVE DIFFICULT CONVERSATIONS IN RELATIONSHIPS ]]></title><description><![CDATA[A Practical Guide to Saying the Hard Things Without Breaking Trust]]></description><link>https://thediaryofaplayboy.substack.com/p/how-to-have-difficult-conversations-c35</link><guid isPermaLink="false">https://thediaryofaplayboy.substack.com/p/how-to-have-difficult-conversations-c35</guid><dc:creator><![CDATA[Martins Itua]]></dc:creator><pubDate>Sun, 28 Jun 2026 10:05:33 GMT</pubDate><enclosure url="iframe.php?url=https%3A%2F%2Fsubstackcdn.com%2Fimage%2Ffetch%2F%24s_%21uUCF%21%2Cf_auto%2Cq_auto%3Agood%2Cfl_progressive%3Asteep%2Fhttps%253A%252F%252Fsubstack-post-media.s3.amazonaws.com%252Fpublic%252Fimages%252F2172e39c-6930-4561-ba19-14c7f32e94bc_1800x2700.png" length="0" type="image/jpeg"/><content:encoded><![CDATA[<div class="captioned-image-container"><figure><a class="image-link image2 is-viewable-img" target="_blank" href="iframe.php?url=https%3A%2F%2Fsubstackcdn.com%2Fimage%2Ffetch%2F%24s_%21uUCF%21%2Cf_auto%2Cq_auto%3Agood%2Cfl_progressive%3Asteep%2Fhttps%253A%252F%252Fsubstack-post-media.s3.amazonaws.com%252Fpublic%252Fimages%252F2172e39c-6930-4561-ba19-14c7f32e94bc_1800x2700.png" data-component-name="Image2ToDOM"><div class="image2-inset"><picture><source type="image/webp" srcset="https://substackcdn.com/image/fetch/$s_!uUCF!,w_424,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F2172e39c-6930-4561-ba19-14c7f32e94bc_1800x2700.png 424w, https://substackcdn.com/image/fetch/$s_!uUCF!,w_848,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F2172e39c-6930-4561-ba19-14c7f32e94bc_1800x2700.png 848w, https://substackcdn.com/image/fetch/$s_!uUCF!,w_1272,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F2172e39c-6930-4561-ba19-14c7f32e94bc_1800x2700.png 1272w, https://substackcdn.com/image/fetch/$s_!uUCF!,w_1456,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F2172e39c-6930-4561-ba19-14c7f32e94bc_1800x2700.png 1456w" sizes="100vw"><img src="iframe.php?url=https%3A%2F%2Fsubstackcdn.com%2Fimage%2Ffetch%2F%24s_%21uUCF%21%2Cw_1456%2Cc_limit%2Cf_auto%2Cq_auto%3Agood%2Cfl_progressive%3Asteep%2Fhttps%253A%252F%252Fsubstack-post-media.s3.amazonaws.com%252Fpublic%252Fimages%252F2172e39c-6930-4561-ba19-14c7f32e94bc_1800x2700.png" width="1456" height="2184" data-attrs="{&quot;src&quot;:&quot;https://substack-post-media.s3.amazonaws.com/public/images/2172e39c-6930-4561-ba19-14c7f32e94bc_1800x2700.png&quot;,&quot;srcNoWatermark&quot;:null,&quot;fullscreen&quot;:null,&quot;imageSize&quot;:null,&quot;height&quot;:2184,&quot;width&quot;:1456,&quot;resizeWidth&quot;:null,&quot;bytes&quot;:3873998,&quot;alt&quot;:null,&quot;title&quot;:null,&quot;type&quot;:&quot;image/png&quot;,&quot;href&quot;:null,&quot;belowTheFold&quot;:false,&quot;topImage&quot;:true,&quot;internalRedirect&quot;:&quot;https://thediaryofaplayboy.substack.com/i/203941738?img=https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F2172e39c-6930-4561-ba19-14c7f32e94bc_1800x2700.png&quot;,&quot;isProcessing&quot;:false,&quot;align&quot;:null,&quot;offset&quot;:false}" class="sizing-normal" alt="" srcset="https://substackcdn.com/image/fetch/$s_!uUCF!,w_424,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F2172e39c-6930-4561-ba19-14c7f32e94bc_1800x2700.png 424w, https://substackcdn.com/image/fetch/$s_!uUCF!,w_848,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F2172e39c-6930-4561-ba19-14c7f32e94bc_1800x2700.png 848w, https://substackcdn.com/image/fetch/$s_!uUCF!,w_1272,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F2172e39c-6930-4561-ba19-14c7f32e94bc_1800x2700.png 1272w, https://substackcdn.com/image/fetch/$s_!uUCF!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F2172e39c-6930-4561-ba19-14c7f32e94bc_1800x2700.png 1456w" sizes="100vw" fetchpriority="high"></picture><div class="image-link-expand"><div class="pencraft pc-display-flex pc-gap-8 pc-reset"><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container restack-image buttonBase-GK1x3M"><svg aria-hidden="true" width="20" height="20" viewBox="0 0 20 20" fill="none" stroke-width="1.5" stroke="var(--color-fg-primary)" stroke-linecap="round" stroke-linejoin="round" xmlns="http://www.w3.org/2000/svg" class="icon-noB79L"><g><path d="M2.53001 7.81595C3.49179 4.73911 6.43281 2.5 9.91173 2.5C13.1684 2.5 15.9537 4.46214 17.0852 7.23684L17.6179 8.67647M17.6179 8.67647L18.5002 4.26471M17.6179 8.67647L13.6473 6.91176M17.4995 12.1841C16.5378 15.2609 13.5967 17.5 10.1178 17.5C6.86118 17.5 4.07589 15.5379 2.94432 12.7632L2.41165 11.3235M2.41165 11.3235L1.5293 15.7353M2.41165 11.3235L6.38224 13.0882"></path></g></svg></button><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container view-image buttonBase-GK1x3M"><svg xmlns="http://www.w3.org/2000/svg" width="20" height="20" viewBox="0 0 24 24" fill="none" stroke="currentColor" stroke-width="2" stroke-linecap="round" stroke-linejoin="round" class="lucide lucide-maximize2 lucide-maximize-2 icon-noB79L"><polyline points="15 3 21 3 21 9"></polyline><polyline points="9 21 3 21 3 15"></polyline><line x1="21" x2="14" y1="3" y2="10"></line><line x1="3" x2="10" y1="21" y2="14"></line></svg></button></div></div></div></a></figure></div><p>Nobody teaches us how to have difficult conversations.</p><p>Not in school.</p><p>Not at home.</p><p>Yet life eventually puts all of us in situations where the right conversation can save a relationship, and the wrong one can destroy it.</p><p>Some relationships don&#8217;t end because people stop loving each other.</p><p>They end because they stop talking.</p><p>Or worse, every difficult conversation becomes another argument, another misunderstanding, or another wound.</p><p>Learning how to have difficult conversations is one of the most valuable relationship skills you&#8217;ll ever develop. It can save a marriage, strengthen a friendship, repair a family, or simply help two people understand each other again.</p><p>That&#8217;s why I wrote <strong>How to Have Difficult Conversations in Relationships</strong>.</p><p>If you&#8217;ve ever walked away from a conversation thinking, <em>&#8220;That&#8217;s not what I meant,&#8221;</em> this guide is for you.</p><p><a href="iframe.php?url=https%3A%2F%2Fbuy.stripe.com%2F5kQ7sMgqkdRA5rY5P6e3e00">Get the Guide Here</a></p><p>I hope it helps you have the conversations that matter most.</p><p><strong>Martins Itua</strong></p>]]></content:encoded></item><item><title><![CDATA[The First Person Who Ever Called Me Daddy]]></title><description><![CDATA[Fatherhood comes with no guarantees. Which is why its greatest rewards are often the ones money cannot buy.]]></description><link>https://thediaryofaplayboy.substack.com/p/the-first-person-who-ever-called</link><guid isPermaLink="false">https://thediaryofaplayboy.substack.com/p/the-first-person-who-ever-called</guid><dc:creator><![CDATA[Martins Itua]]></dc:creator><pubDate>Sun, 21 Jun 2026 17:08:08 GMT</pubDate><enclosure url="iframe.php?url=https%3A%2F%2Fsubstackcdn.com%2Fimage%2Ffetch%2F%24s_%21zJpi%21%2Cw_256%2Cc_limit%2Cf_auto%2Cq_auto%3Agood%2Cfl_progressive%3Asteep%2Fhttps%253A%252F%252Fsubstack-post-media.s3.amazonaws.com%252Fpublic%252Fimages%252F3bc0642f-a38f-4158-a45e-047c9a73c998_1024x1024.png" length="0" type="image/jpeg"/><content:encoded><![CDATA[<p>My phone rang on Father&#8217;s Day.</p><p>It was my daughter.</p><div class="subscription-widget-wrap-editor" data-attrs="{&quot;url&quot;:&quot;https://thediaryofaplayboy.substack.com/subscribe?&quot;,&quot;text&quot;:&quot;Subscribe&quot;,&quot;language&quot;:&quot;en&quot;}" data-component-name="SubscribeWidgetToDOM"><div class="subscription-widget show-subscribe"><div class="preamble"><p class="cta-caption">The Diary of a Playboy is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.</p></div><form class="subscription-widget-subscribe"><input type="email" class="email-input" name="email" placeholder="Type your email&#8230;" tabindex="-1"><input type="submit" class="button primary" value="Subscribe"><div class="fake-input-wrapper"><div class="fake-input"></div><div class="fake-button"></div></div></form></div></div><p>She is now a university student.</p><p>The little girl who once needed help crossing the road is becoming a woman.</p><p>A capable one.</p><p>A thoughtful one.</p><p>A determined one.</p><p>She called to wish me a Happy Father&#8217;s Day.</p><p>As we spoke, I found myself telling her something I had never said quite this way before.</p><p>I told her that I would always be grateful that she was the first person who ever called me Daddy.</p><p>She laughed.</p><p>But I meant every word.</p><p>Of all the titles I have carried in my life, that one remains the most important.</p><p>Not Managing Director.</p><p>Not Chairman.</p><p>Not Author.</p><p>Not any professional title that appears on a business card.</p><p>Daddy.</p><p>That was the title that changed everything.</p><p>During the conversation, she shared her second year university results with me.</p><p>She had done very well.</p><p>Very well.</p><p>And as I listened to her speak, I felt something every parent will recognize.</p><p>Pride.</p><p>Not the loud kind.</p><p>Not the boastful kind.</p><p>The quiet kind.</p><p>The kind that sits in your chest and reminds you that some things matter more than money, status, or success.</p><p>I told her how proud I was of her.</p><p>I told her she was becoming an extraordinary young woman.</p><p>I told her she would go on to do record breaking things in the world.</p><p>And then I told her something else.</p><p>I told her to remember those words.</p><p>Always.</p><p>Because there will come a time when life becomes difficult.</p><p>A time when she questions herself.</p><p>A time when someone tells her she cannot do something.</p><p>And when that day comes, I want her to remember what her father saw in her long before the world did.</p><p>Eventually, the conversation ended the way many conversations between parents and children do.</p><p>Simple words.</p><p>Words we often say without fully appreciating them.</p><p>&#8220;I love you forever.&#8221;</p><p>&#8220;I love you, too, Dad.&#8221;</p><p>Then the call ended.</p><p>And I sat there for a moment thinking about fatherhood.</p><p>Because fatherhood is one of the strangest journeys a person can undertake.</p><p>You spend years giving.</p><p>Years worrying.</p><p>Years sacrificing.</p><p>Years teaching lessons that seem to go unheard.</p><p>Years paying bills.</p><p>Years making decisions.</p><p>Years hoping you got more things right than wrong.</p><p>And all the while, there is no guarantee of anything in return.</p><p>No contract.</p><p>No certainty.</p><p>No promise.</p><p>Nothing.</p><p>Only faith.</p><p>Faith that the seeds you are planting today will someday grow into something beautiful.</p><p>And that may be what makes fatherhood unique.</p><p>It is one of the few investments where the return is never guaranteed.</p><div class="native-video-embed" data-component-name="VideoPlaceholder" data-attrs="{&quot;mediaUploadId&quot;:&quot;d073939e-065d-4ede-b06d-8428116c4841&quot;,&quot;duration&quot;:null}"></div><p><strong>A friend shared an observation about fatherhood with me today and it stayed with me.</strong></p><p>He called it &#8220;psychic income.&#8221;</p><p>The rewards that cannot be measured.</p><p>The returns that never appear on a bank statement.</p><p>The profits that exist only in the heart.</p><p>The older I get, the more I think he was right.</p><p>Because fatherhood comes with no guarantees.</p><p>None.</p><p>A man can neglect his children and still find himself loved, respected, cared for, and celebrated by them later in life.</p><p>Another man can sacrifice everything.</p><p>His sleep.</p><p>His comfort.</p><p>His ambitions.</p><p>His money.</p><p>His peace of mind.</p><p>And still find himself distant from the very children he devoted his life to raising.</p><p>Life is strange that way.</p><p>Love is not accounting.</p><p>Parenthood is not mathematics.</p><p>The equation does not always balance.</p><p>That may be one of the hardest truths fathers eventually learn.</p><p>You cannot parent for the reward.</p><p>You cannot love your children because you expect repayment.</p><p>You cannot sacrifice because you are guaranteed appreciation.</p><p>Because there are no guarantees.</p><p>And perhaps there shouldn&#8217;t be.</p><p>Children are not investment portfolios.</p><p>They are human beings.</p><p>They arrive carrying their own personalities, choices, strengths, weaknesses, dreams, wounds, and destinies.</p><p>Every parent influences them.</p><p>No parent controls them.</p><p>That distinction matters.</p><p>I have met fathers who measure their success entirely by outcomes.</p><p>Did the child become wealthy?</p><p>Did the child become successful?</p><p>Did the child become famous?</p><p>Did the child make them proud?</p><p>But the older I get, the less convinced I am that these are the right questions.</p><p>Because success has many fathers.</p><p>So does failure.</p><p>Some wonderful parents raise troubled children.</p><p>Some troubled parents raise remarkable children.</p><p>And most families exist somewhere in between.</p><p>The real miracle of fatherhood is not control.</p><p>It is influence.</p><p>It is the privilege of helping shape another human being while knowing that one day they must leave your hands and make their own way in the world.</p><p>That is not easy.</p><p>In fact, it may be one of the most difficult assignments life gives us.</p><p>You spend years teaching.</p><p>Then life starts teaching them too.</p><p>You spend years protecting them.</p><p>Then eventually you cannot.</p><p>You spend years making decisions for them.</p><p>Then one day they begin making decisions for themselves.</p><p>And all you can do is hope that something of what you taught them remains.</p><p>Hope that your values survive the journey.</p><p>Hope that your love survives the distance.</p><p>Hope that your voice remains in their heads long after they stop needing your permission.</p><p>I think that is why my daughter&#8217;s call affected me so deeply.</p><p>It was not really about Father&#8217;s Day.</p><p>It was not even about her results.</p><p>It was the realization that the little girl who once held my hand is becoming exactly what every father secretly hopes for.</p><p>Not perfect.</p><p>Not famous.</p><p>Not wealthy.</p><p>But capable.</p><p>Thoughtful.</p><p>Responsible.</p><p>Kind.</p><p>Someone who is building her own life with purpose and determination.</p><p>And in that moment, I understood something many fathers discover only with time.</p><p>The greatest reward of fatherhood is not what your children give back to you.</p><p>It is who they become.</p><p>Because one day, if you are fortunate, you stop seeing the child you raised.</p><p>And you begin seeing the adult they are becoming.</p><p>There are few moments more beautiful than that.</p><p><strong>Perhaps that is why fatherhood is unlike any other role we will ever play.</strong></p><p>Because so much of it happens in the dark.</p><p>The world celebrates outcomes.</p><p>Fathers live with uncertainty.</p><p>Nobody sees the prayers.</p><p>Nobody sees the worries.</p><p>Nobody sees the sleepless nights.</p><p>Nobody sees the sacrifices.</p><p>Nobody sees the quiet calculations.</p><p>The opportunities postponed.</p><p>The risks taken.</p><p>The burdens carried.</p><p>The fears hidden.</p><p>Most of fatherhood happens without applause.</p><p>And yet fathers continue.</p><p>Not because they are guaranteed gratitude.</p><p>Not because they are guaranteed affection.</p><p>Not because they are guaranteed recognition.</p><p>They continue because love rarely asks for guarantees.</p><p>I have come to believe that one of the most important things a father gives a child is belief.</p><p>Before the world tells them who they are.</p><p>Before success confirms it.</p><p>Before achievement validates it.</p><p>A father has the opportunity to plant something extraordinary.</p><p>Confidence.</p><p>Courage.</p><p>Conviction.</p><p>The belief that they can do difficult things.</p><p>The belief that they are capable.</p><p>The belief that they matter.</p><p>That is why the words we speak to our children are so important.</p><p>Years from now, my daughter may not remember this Father&#8217;s Day conversation exactly as it happened.</p><p>She may not remember every sentence.</p><p>She may not remember every detail.</p><p>But I hope she remembers the certainty.</p><p>The certainty with which her father told her that she was capable of extraordinary things.</p><p>Many of us are still living on confidence someone gave us years ago.</p><p>A teacher.</p><p>A mother.</p><p>A father.</p><p>Someone who saw something in us before we could see it ourselves.</p><p>The opposite is also true.</p><p>Many people spend their adult lives trying to recover from words that were never spoken.</p><p>Encouragement never given.</p><p>Belief never expressed.</p><p>Potential never acknowledged.</p><p>Because life will eventually test that belief.</p><p>Life tests everyone.</p><p>There will be setbacks.</p><p>Failures.</p><p>Disappointments.</p><p>Moments of doubt.</p><p>Moments when the world appears unconvinced.</p><p>And on those days, I hope she remembers what I saw in her.</p><p>Not because fathers are always right.</p><p>But because sometimes a parent&#8217;s belief becomes the foundation upon which a child builds their own.</p><p>That may be one of the greatest gifts we ever leave behind.</p><p>Not money.</p><p>Not property.</p><p>Not achievements.</p><p>But belief.</p><p>The belief that allows another human being to become fully themselves.</p><p>And perhaps that is what I was really celebrating when my phone rang on Father&#8217;s Day.</p><p>Not a title.</p><p>Not a tradition.</p><p>Not even a relationship.</p><p>But the privilege of witnessing a life unfold.</p><p>The privilege of watching a little girl become a young woman.</p><p>The privilege of knowing that some small part of who I am may travel with her long after I am gone.</p><p>When I told her I would always be grateful that she was the first person who ever called me Daddy, I wasn&#8217;t talking about a word.</p><p>I was talking about a journey.</p><p>A responsibility.</p><p>A blessing.</p><p>A privilege.</p><p>And if fatherhood has taught me anything, it is this:</p><p>The greatest rewards in life are rarely the ones you can measure.</p><p>They are the ones you feel.</p><p>A phone call.</p><p>A conversation.</p><p>A moment of pride.</p><p>A simple &#8220;I love you.&#8221;</p><p>The knowledge that someone you once carried in your arms is now carrying themselves through the world.</p><p>And carrying themselves well.</p><p>For every father reading this today, I hope the lines have fallen in pleasant places for you.</p><p>And for those still waiting for their rewards, may you never underestimate the seeds you have planted.</p><p>Because the most beautiful returns often arrive quietly.</p><p>Sometimes years later.</p><p>Sometimes in a phone call.</p><p>Sometimes in a child who makes you realize that all those years of loving, teaching, worrying, and hoping were never wasted after all.</p><p>Happy Father&#8217;s Day.</p><p>Until next time,</p><p><strong>Martins</strong></p><p><em>The Diary of a Playboy</em></p><div class="subscription-widget-wrap-editor" data-attrs="{&quot;url&quot;:&quot;https://thediaryofaplayboy.substack.com/subscribe?&quot;,&quot;text&quot;:&quot;Subscribe&quot;,&quot;language&quot;:&quot;en&quot;}" data-component-name="SubscribeWidgetToDOM"><div class="subscription-widget show-subscribe"><div class="preamble"><p class="cta-caption">The Diary of a Playboy is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.</p></div><form class="subscription-widget-subscribe"><input type="email" class="email-input" name="email" placeholder="Type your email&#8230;" tabindex="-1"><input type="submit" class="button primary" value="Subscribe"><div class="fake-input-wrapper"><div class="fake-input"></div><div class="fake-button"></div></div></form></div></div>]]></content:encoded></item><item><title><![CDATA[What Happens When the Life You Planned Never Arrives]]></title><description><![CDATA[The hardest grief is often for a future that never happened.]]></description><link>https://thediaryofaplayboy.substack.com/p/what-happens-when-the-life-you-planned</link><guid isPermaLink="false">https://thediaryofaplayboy.substack.com/p/what-happens-when-the-life-you-planned</guid><dc:creator><![CDATA[Martins Itua]]></dc:creator><pubDate>Sat, 20 Jun 2026 16:39:13 GMT</pubDate><enclosure url="iframe.php?url=https%3A%2F%2Fsubstackcdn.com%2Fimage%2Ffetch%2F%24s_%21OIH2%21%2Cf_auto%2Cq_auto%3Agood%2Cfl_progressive%3Asteep%2Fhttps%253A%252F%252Fsubstack-post-media.s3.amazonaws.com%252Fpublic%252Fimages%252F728fb2bc-43c6-4dd2-bd6b-5c4613cd943a_1024x1536.png" length="0" type="image/jpeg"/><content:encoded><![CDATA[<p>She sat alone on her fortieth birthday.</p><p>Not because nobody loved her.</p><div class="subscription-widget-wrap-editor" data-attrs="{&quot;url&quot;:&quot;https://thediaryofaplayboy.substack.com/subscribe?&quot;,&quot;text&quot;:&quot;Subscribe&quot;,&quot;language&quot;:&quot;en&quot;}" data-component-name="SubscribeWidgetToDOM"><div class="subscription-widget show-subscribe"><div class="preamble"><p class="cta-caption">The Diary of a Playboy is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.</p></div><form class="subscription-widget-subscribe"><input type="email" class="email-input" name="email" placeholder="Type your email&#8230;" tabindex="-1"><input type="submit" class="button primary" value="Subscribe"><div class="fake-input-wrapper"><div class="fake-input"></div><div class="fake-button"></div></div></form></div></div><p>Not because she was broken.</p><p>Not because she had failed.</p><p>In fact, by most measures, her life looked fine.</p><p>She had a good job.</p><p>A comfortable home.</p><p>Close friends.</p><p>Enough money to pay her bills and occasionally travel.</p><p>From the outside, there was very little to complain about.</p><p>Yet as she sat there that evening, staring at a cake she had bought for herself, she found herself crying.</p><p>Not because of what she had.</p><p>Because of what she didn&#8217;t.</p><p>When she was twenty, forty looked very different.</p><p>There would be a husband.</p><p>There would be children.</p><p>There would be family vacations and Christmas photographs and school runs and all the ordinary moments she had spent decades imagining.</p><p>That life had felt so certain that she never questioned it.</p><p>It wasn&#8217;t a dream.</p><p>It was a plan.</p><p>A timeline.</p><p>A future she expected to arrive the same way people expect summer after spring.</p><p>And yet here she was.</p><p>Forty.</p><p>Alone.</p><p>Not devastated.</p><p>Not hopeless.</p><p>Just standing in the uncomfortable space between the life she imagined and the life she actually lived.</p><p><em><strong><span data-color="#ff6719" style="color: rgb(255, 103, 25);">The truth is that almost everyone knows this feeling.</span></strong></em></p><p>The details change.</p><p>The feeling does not.</p><p>The man who thought he would be wealthy by now.</p><p>The entrepreneur who thought the business would succeed.</p><p>The couple who thought they would have children.</p><p>The graduate who believed a degree certificate alone would open doors.</p><p>The athlete whose body gave out too soon.</p><p>The immigrant who thought a new country would solve old problems.</p><p>The parent who imagined a different future for their child.</p><p>Most of us carry an invisible picture of how life is supposed to unfold.</p><p>Then reality arrives.</p><p>And reality rarely asks for permission.</p><p>Nobody prepares us for that.</p><p>We are taught how to set goals.</p><p>How to plan.</p><p>How to dream.</p><p>How to work.</p><p>How to strive.</p><p>But we are very rarely taught what to do when life ignores the script.</p><p>What happens when the marriage never comes?</p><p>What happens when the promotion never arrives?</p><p>What happens when the business fails?</p><p>What happens when the family falls apart?</p><p>What happens when the future you spent years preparing for simply never materializes?</p><p>Because that is not just disappointment.</p><p>It is grief.</p><p>And grief is not limited to people who die.</p><p>Sometimes we grieve possibilities.</p><p>Sometimes we grieve futures.</p><p>Sometimes we grieve versions of ourselves that never got the chance to exist.</p><p>And that grief can last for years without us even recognizing it.</p><div class="captioned-image-container"><figure><a class="image-link image2 is-viewable-img" target="_blank" href="iframe.php?url=https%3A%2F%2Fsubstackcdn.com%2Fimage%2Ffetch%2F%24s_%21OIH2%21%2Cf_auto%2Cq_auto%3Agood%2Cfl_progressive%3Asteep%2Fhttps%253A%252F%252Fsubstack-post-media.s3.amazonaws.com%252Fpublic%252Fimages%252F728fb2bc-43c6-4dd2-bd6b-5c4613cd943a_1024x1536.png" data-component-name="Image2ToDOM"><div class="image2-inset"><picture><source type="image/webp" srcset="https://substackcdn.com/image/fetch/$s_!OIH2!,w_424,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F728fb2bc-43c6-4dd2-bd6b-5c4613cd943a_1024x1536.png 424w, https://substackcdn.com/image/fetch/$s_!OIH2!,w_848,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F728fb2bc-43c6-4dd2-bd6b-5c4613cd943a_1024x1536.png 848w, https://substackcdn.com/image/fetch/$s_!OIH2!,w_1272,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F728fb2bc-43c6-4dd2-bd6b-5c4613cd943a_1024x1536.png 1272w, https://substackcdn.com/image/fetch/$s_!OIH2!,w_1456,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F728fb2bc-43c6-4dd2-bd6b-5c4613cd943a_1024x1536.png 1456w" sizes="auto, 100vw"><img src="iframe.php?url=https%3A%2F%2Fsubstackcdn.com%2Fimage%2Ffetch%2F%24s_%21OIH2%21%2Cw_1456%2Cc_limit%2Cf_auto%2Cq_auto%3Agood%2Cfl_progressive%3Asteep%2Fhttps%253A%252F%252Fsubstack-post-media.s3.amazonaws.com%252Fpublic%252Fimages%252F728fb2bc-43c6-4dd2-bd6b-5c4613cd943a_1024x1536.png" width="1024" height="1536" data-attrs="{&quot;src&quot;:&quot;https://substack-post-media.s3.amazonaws.com/public/images/728fb2bc-43c6-4dd2-bd6b-5c4613cd943a_1024x1536.png&quot;,&quot;srcNoWatermark&quot;:null,&quot;fullscreen&quot;:null,&quot;imageSize&quot;:null,&quot;height&quot;:1536,&quot;width&quot;:1024,&quot;resizeWidth&quot;:null,&quot;bytes&quot;:2526883,&quot;alt&quot;:null,&quot;title&quot;:null,&quot;type&quot;:&quot;image/png&quot;,&quot;href&quot;:null,&quot;belowTheFold&quot;:true,&quot;topImage&quot;:false,&quot;internalRedirect&quot;:&quot;https://thediaryofaplayboy.substack.com/i/202857281?img=https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F728fb2bc-43c6-4dd2-bd6b-5c4613cd943a_1024x1536.png&quot;,&quot;isProcessing&quot;:false,&quot;align&quot;:null,&quot;offset&quot;:false}" class="sizing-normal" alt="" srcset="https://substackcdn.com/image/fetch/$s_!OIH2!,w_424,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F728fb2bc-43c6-4dd2-bd6b-5c4613cd943a_1024x1536.png 424w, https://substackcdn.com/image/fetch/$s_!OIH2!,w_848,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F728fb2bc-43c6-4dd2-bd6b-5c4613cd943a_1024x1536.png 848w, https://substackcdn.com/image/fetch/$s_!OIH2!,w_1272,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F728fb2bc-43c6-4dd2-bd6b-5c4613cd943a_1024x1536.png 1272w, https://substackcdn.com/image/fetch/$s_!OIH2!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F728fb2bc-43c6-4dd2-bd6b-5c4613cd943a_1024x1536.png 1456w" sizes="auto, 100vw" loading="lazy"></picture><div class="image-link-expand"><div class="pencraft pc-display-flex pc-gap-8 pc-reset"><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container restack-image buttonBase-GK1x3M"><svg aria-hidden="true" width="20" height="20" viewBox="0 0 20 20" fill="none" stroke-width="1.5" stroke="var(--color-fg-primary)" stroke-linecap="round" stroke-linejoin="round" xmlns="http://www.w3.org/2000/svg" class="icon-noB79L"><g><path d="M2.53001 7.81595C3.49179 4.73911 6.43281 2.5 9.91173 2.5C13.1684 2.5 15.9537 4.46214 17.0852 7.23684L17.6179 8.67647M17.6179 8.67647L18.5002 4.26471M17.6179 8.67647L13.6473 6.91176M17.4995 12.1841C16.5378 15.2609 13.5967 17.5 10.1178 17.5C6.86118 17.5 4.07589 15.5379 2.94432 12.7632L2.41165 11.3235M2.41165 11.3235L1.5293 15.7353M2.41165 11.3235L6.38224 13.0882"></path></g></svg></button><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container view-image buttonBase-GK1x3M"><svg xmlns="http://www.w3.org/2000/svg" width="20" height="20" viewBox="0 0 24 24" fill="none" stroke="currentColor" stroke-width="2" stroke-linecap="round" stroke-linejoin="round" class="lucide lucide-maximize2 lucide-maximize-2 icon-noB79L"><polyline points="15 3 21 3 21 9"></polyline><polyline points="9 21 3 21 3 15"></polyline><line x1="21" x2="14" y1="3" y2="10"></line><line x1="3" x2="10" y1="21" y2="14"></line></svg></button></div></div></div></a></figure></div><p><strong><span data-color="#ff6719" style="color: rgb(255, 103, 25);">The first mistake most people make is believing that disappointment means they did something wrong.</span></strong></p><p>Sometimes it does.</p><p>Sometimes poor decisions have consequences.</p><p>Sometimes we ignore warning signs.</p><p>Sometimes we stay too long.</p><p>Sometimes we quit too early.</p><p>Sometimes we sabotage ourselves.</p><p>But not everything that goes wrong is the result of failure.</p><p>That is one of the most important lessons adulthood teaches.</p><p>You can do everything right and still lose.</p><p>You can be a good spouse and still get divorced.</p><p>You can be a good parent and still watch your child struggle.</p><p>You can work hard and still be passed over.</p><p>You can build carefully and still watch everything collapse.</p><p>Life is not a vending machine where good behaviour guarantees the desired outcome.</p><p>And much of our suffering begins when we refuse to accept that reality.</p><p>We keep asking questions that have no answers.</p><p>Why me?</p><p>Why now?</p><p>Why did this happen?</p><p>What did I do wrong?</p><p>Sometimes there is an answer.</p><p>Often there isn&#8217;t.</p><p><strong><span data-color="#ff6719" style="color: rgb(255, 103, 25);">The second mistake is even more painful.</span></strong></p><p>We continue living in a future that no longer exists.</p><p>The woman who expected marriage at thirty is now forty five.</p><p>Yet part of her is still emotionally waiting for the life she imagined twenty years ago.</p><p>The entrepreneur whose company failed five years ago still measures every day against the success he expected.</p><p>The divorced man continues comparing reality to the marriage he thought he would have.</p><p>The parent whose child took a different path keeps grieving the future they planned instead of seeing the person standing in front of them.</p><p>This happens more often than people realize.</p><p>The future becomes a ghost.</p><p>And ghosts are difficult to let go of.</p><p>Not because they are real.</p><p>But because they once felt real.</p><p>The problem is that every moment spent arguing with reality is a moment we cannot fully live.</p><p>I once knew a man who spent twenty years talking about a business opportunity that failed.</p><p>Twenty years.</p><p>Every conversation eventually returned to it.</p><p>Every setback traced back to it.</p><p>Every disappointment connected to it.</p><p>He wasn&#8217;t living in the present.</p><p>He was living inside an alternate timeline.</p><p>A life that never happened.</p><p>And that is the hidden danger.</p><p>Many people never recover from disappointment because they never stop negotiating with the past.</p><p>They keep trying to rewrite a chapter that has already been printed.</p><p>What makes this especially difficult is that society constantly reinforces it.</p><p>At twenty five, people ask when you will get married.</p><p>At thirty five, they ask when you will have children.</p><p>At forty, they ask why you haven&#8217;t.</p><p>Success has timelines.</p><p>Relationships have timelines.</p><p>Careers have timelines.</p><p>Life has timelines.</p><p>Or so we are told.</p><p>What nobody mentions is that life rarely follows schedules.</p><p>Some people find love at twenty.</p><p>Others at sixty.</p><p>Some people become successful at thirty.</p><p>Others at seventy.</p><p>Some dreams arrive late.</p><p>Some arrive differently.</p><p>Some never arrive at all.</p><p>And perhaps that is the hardest truth of all.</p><p>Not every dream comes true.</p><p>Not every plan succeeds.</p><p>Not every prayer is answered the way we hoped.</p><p>Not every story ends the way we imagined.</p><p>For many people, that sentence feels unbearable.</p><p>Because we are taught to believe that persistence guarantees outcomes.</p><p>That if we want something badly enough, work hard enough, sacrifice enough, eventually life will cooperate.</p><p>Sometimes it does.</p><p>Sometimes it doesn&#8217;t.</p><p>The older I get, the more I realize that maturity is not learning how to get everything you want.</p><p>It is learning how to live when you don&#8217;t.</p><p>That sounds pessimistic.</p><p>It isn&#8217;t.</p><p>In fact, it may be one of the most liberating truths in the world.</p><p>Because the moment you stop demanding that life match your expectations, something unexpected happens.</p><p>You become available to the life that is actually unfolding.</p><p>And sometimes that life contains possibilities you could never have planned.</p><p>Not because disappointment is beautiful.</p><p>Not because loss is a gift.</p><p><em><strong><span data-color="#ff6719" style="color: rgb(255, 103, 25);">But because reality can only begin where fantasy ends.</span></strong></em></p><p><strong>Perhaps the deepest pain is not what happened.</strong></p><p>It is what never happened.</p><p>There is a difference.</p><p>A woman can survive a divorce.</p><p>What haunts her for years is often not the divorce itself.</p><p>It is the family she thought she would still have.</p><p>The Christmas mornings she imagined.</p><p>The growing old together she expected.</p><p>The future she had quietly built inside her mind.</p><p>A man can survive losing a business.</p><p>What keeps him awake at night is often not the financial loss.</p><p>It is the life he had already spent years living in his imagination.</p><p>The house.</p><p>The freedom.</p><p>The success.</p><p>The version of himself he expected to become.</p><p>The loss happened once.</p><p>The imagined future dies a thousand times.</p><p>And that is why some disappointments linger for decades.</p><p>The event ended.</p><p>The expectation did not.</p><p>Most people do not realize this.</p><p>They think they are grieving reality.</p><p>Often they are grieving imagination.</p><p>A future that felt so certain it became part of their identity.</p><p>A future they never considered might not arrive.</p><p>That is why letting go can feel so impossible.</p><p>Because letting go is not just releasing a dream.</p><p>It is releasing a version of yourself.</p><p>The mother you expected to be.</p><p>The husband you expected to become.</p><p>The entrepreneur you thought you would be.</p><p>The life you assumed was waiting around the corner.</p><p>And there is no funeral for those losses.</p><p>Nobody sends flowers.</p><p>Nobody checks in.</p><p>Nobody says:</p><p>&#8220;I am sorry for the future you never got.&#8221;</p><p>Yet those losses can be devastating.</p><p>I once met a man who spent most of his life trying to become a professional athlete.</p><p>Everything revolved around it.</p><p>His identity.</p><p>His friendships.</p><p>His ambitions.</p><p>His sense of purpose.</p><p>Then an injury ended the possibility forever.</p><p>Not temporarily.</p><p>Forever.</p><p>Years later, he still spoke about it.</p><p>Not because he wanted sympathy.</p><p>Because part of him never left that moment.</p><p>Part of him was still standing at the edge of a life that never happened.</p><p>Waiting.</p><p>Many people do the same thing.</p><p>They are physically present but emotionally elsewhere.</p><p>Still waiting for the call.</p><p>The promotion.</p><p>The apology.</p><p>The marriage.</p><p>The opportunity.</p><p>The breakthrough.</p><p>The version of life they expected.</p><p>The problem is that while they are waiting for the life they lost, they miss the life they have.</p><p><strong><span data-color="#ff6719" style="color: rgb(255, 103, 25);">And that may be the greatest tragedy of all.</span></strong></p><p>Not that the dream died.</p><p>But that reality never got a chance.</p><p>Because reality is imperfect.</p><p>Reality rarely looks like the vision board.</p><p>Reality arrives with compromises.</p><p>Detours.</p><p>Surprises.</p><p>Heartbreaks.</p><p>Unexpected turns.</p><p>Reality is messier than the life we planned.</p><p>But it is also the only place where life can actually be lived.</p><p>At some point, every person faces a question that no one can answer for them.</p><p>How long will you wait for a future that is no longer coming?</p><p>Not because hope is bad.</p><p>Hope is essential.</p><p>But because there is a difference between hope and attachment.</p><p>Hope looks forward.</p><p>Attachment keeps looking back.</p><p>And sometimes healing begins when we stop asking why life did not give us the story we wanted.</p><p>And start asking what story is still possible from here.</p><p>That question changes everything.</p><p>Because it shifts our attention from what was lost to what remains.</p><p>From what never happened to what still can.</p><p>From grief to possibility.</p><p><em><strong><span data-color="#ff6719" style="color: rgb(255, 103, 25);">And that is often where a new life begins.</span></strong></em></p><p>Maybe that is what growing older really is.</p><p>Not accumulating answers.</p><p>Not achieving every goal.</p><p>Not arriving at the life you imagined when you were twenty.</p><p>Perhaps it is learning how to love the life that arrived instead.</p><p>The older I get, the more I realize that almost everyone is carrying an invisible grief.</p><p>The career that never happened.</p><p>The marriage that ended.</p><p>The child that never came.</p><p>The dream that quietly slipped away.</p><p>The future that looked certain until it wasn&#8217;t.</p><p>Some people spend their entire lives fighting reality because reality failed to follow the plan.</p><p>Others eventually discover something profound.</p><p>Life is not asking us to approve of everything that happened.</p><p>Life is asking us to live anyway.</p><p>To find meaning anyway.</p><p>To love anyway.</p><p>To hope anyway.</p><p>To build anyway.</p><p>Because while some futures never arrive, others cannot begin until we stop waiting for the first one.</p><p>And perhaps that is the hidden gift inside disappointment.</p><p>Not that it feels good.</p><p>Not that it makes sense.</p><p>But that it forces us to meet life as it is, not as we imagined it would be.</p><p>And sometimes the life waiting on the other side of acceptance is richer, deeper, and more meaningful than the one we originally planned.</p><p><strong><span data-color="#ff6719" style="color: rgb(255, 103, 25);">Not because it is perfect.</span></strong></p><p><strong><span data-color="#ff6719" style="color: rgb(255, 103, 25);">But because it is real.</span></strong></p><p>If this resonated with you, share it with someone who may be grieving a future that never arrived.</p><p>Someone learning to make peace with the gap between expectation and reality.</p><p>Someone who needs to know they are not alone.</p><p>And if these are the kinds of conversations you wish more people were having, subscribe and join us.</p><p>The Diary of a Playboy is a space for exploring the hidden forces that shape our relationships, decisions, families, beliefs, careers, and lives.</p><p>Finally, if this piece made you pause, reflect, or see your own story differently, consider buying the author a coffee.</p><p>It helps support the writing and keeps these conversations alive.</p><p>Until next time,</p><p><strong>Martins</strong></p><p><em>The Diary of a Playboy</em></p><div class="subscription-widget-wrap-editor" data-attrs="{&quot;url&quot;:&quot;https://thediaryofaplayboy.substack.com/subscribe?&quot;,&quot;text&quot;:&quot;Subscribe&quot;,&quot;language&quot;:&quot;en&quot;}" data-component-name="SubscribeWidgetToDOM"><div class="subscription-widget show-subscribe"><div class="preamble"><p class="cta-caption">The Diary of a Playboy is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.</p></div><form class="subscription-widget-subscribe"><input type="email" class="email-input" name="email" placeholder="Type your email&#8230;" tabindex="-1"><input type="submit" class="button primary" value="Subscribe"><div class="fake-input-wrapper"><div class="fake-input"></div><div class="fake-button"></div></div></form></div></div>]]></content:encoded></item><item><title><![CDATA[What People Call Ancestral Curses Are Often Inherited Patterns]]></title><description><![CDATA[The most dangerous things passed down through generations are not spirits. They are beliefs, behaviours, fears, and stories nobody ever thought to question.]]></description><link>https://thediaryofaplayboy.substack.com/p/what-people-call-ancestral-curses</link><guid isPermaLink="false">https://thediaryofaplayboy.substack.com/p/what-people-call-ancestral-curses</guid><dc:creator><![CDATA[Martins Itua]]></dc:creator><pubDate>Sun, 14 Jun 2026 14:51:27 GMT</pubDate><enclosure url="iframe.php?url=https%3A%2F%2Fsubstackcdn.com%2Fimage%2Ffetch%2F%24s_%21cWjm%21%2Cf_auto%2Cq_auto%3Agood%2Cfl_progressive%3Asteep%2Fhttps%253A%252F%252Fsubstack-post-media.s3.amazonaws.com%252Fpublic%252Fimages%252F2ef108bf-e3fd-4f74-82dd-cd82a457194a_1024x1536.png" length="0" type="image/jpeg"/><content:encoded><![CDATA[<p>A woman came to see me years ago.</p><p>She was convinced there was a curse on her family.</p><div class="subscription-widget-wrap-editor" data-attrs="{&quot;url&quot;:&quot;https://thediaryofaplayboy.substack.com/subscribe?&quot;,&quot;text&quot;:&quot;Subscribe&quot;,&quot;language&quot;:&quot;en&quot;}" data-component-name="SubscribeWidgetToDOM"><div class="subscription-widget show-subscribe"><div class="preamble"><p class="cta-caption">The Diary of a Playboy is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.</p></div><form class="subscription-widget-subscribe"><input type="email" class="email-input" name="email" placeholder="Type your email&#8230;" tabindex="-1"><input type="submit" class="button primary" value="Subscribe"><div class="fake-input-wrapper"><div class="fake-input"></div><div class="fake-button"></div></div></form></div></div><p>Her mother had her first child at sixteen.</p><p>She had her first child at fifteen.</p><p>Now her daughter was pregnant at fourteen.</p><p>Three generations.</p><p>The same story.</p><p>The same outcome.</p><p>The same heartbreak.</p><p>&#8220;If that isn&#8217;t a curse,&#8221; she asked, &#8220;what else could it be?&#8221;</p><p>It is a fair question.</p><p>After all, how many times does something have to happen before it stops looking like coincidence and starts looking like destiny?</p><p>Most of us have seen families like this.</p><p>The family where every marriage fails.</p><p>The family where alcoholism passes from one generation to the next.</p><p>The family where fathers disappear.</p><p>The family where daughters keep choosing the same kind of man.</p><p>The family where money comes in but never stays.</p><p>The family where everyone seems trapped in the same cycle despite their best intentions.</p><p>And whenever these patterns repeat long enough, someone eventually says the words.</p><p>&#8220;There is a curse on this family.&#8221;</p><p>Perhaps.</p><p>But what if there is another explanation?</p><p>What if the thing we are calling a curse is often something far more ordinary and far more dangerous?</p><p>What if children inherit more than their parents&#8217; eyes, height, or skin colour?</p><p>What if they inherit beliefs?</p><p>What if they inherit fears?</p><p>What if they inherit habits?</p><p>What if they inherit emotional wounds?</p><p>What if they inherit stories about what is possible, what is normal, what is expected, and what kind of life people like them are supposed to live?</p><p>And what if those things are powerful enough to shape generations?</p><p>Because here is an uncomfortable truth.</p><p>Human beings have always attributed to God, the devil, fate, destiny, luck, and curses the things they could not explain.</p><p>Sometimes that explanation is correct.</p><p>But sometimes it is simply easier.</p><p>It is easier to blame a curse than to confront a pattern.</p><p>Easier to blame the devil than to examine a behaviour.</p><p>Easier to pray against a problem than to understand it.</p><p>Because understanding often comes with something many people would rather avoid.</p><p>Responsibility.</p><p>And responsibility changes everything.</p><p>Because a curse requires deliverance.</p><p>A pattern requires awareness.</p><p>A curse requires rescue.</p><p>A pattern requires change.</p><p>And those are very different conversations.</p><p>This article is about one of them.</p><div class="captioned-image-container"><figure><a class="image-link image2 is-viewable-img" target="_blank" href="iframe.php?url=https%3A%2F%2Fsubstackcdn.com%2Fimage%2Ffetch%2F%24s_%21cWjm%21%2Cf_auto%2Cq_auto%3Agood%2Cfl_progressive%3Asteep%2Fhttps%253A%252F%252Fsubstack-post-media.s3.amazonaws.com%252Fpublic%252Fimages%252F2ef108bf-e3fd-4f74-82dd-cd82a457194a_1024x1536.png" data-component-name="Image2ToDOM"><div class="image2-inset"><picture><source type="image/webp" srcset="https://substackcdn.com/image/fetch/$s_!cWjm!,w_424,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F2ef108bf-e3fd-4f74-82dd-cd82a457194a_1024x1536.png 424w, https://substackcdn.com/image/fetch/$s_!cWjm!,w_848,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F2ef108bf-e3fd-4f74-82dd-cd82a457194a_1024x1536.png 848w, https://substackcdn.com/image/fetch/$s_!cWjm!,w_1272,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F2ef108bf-e3fd-4f74-82dd-cd82a457194a_1024x1536.png 1272w, https://substackcdn.com/image/fetch/$s_!cWjm!,w_1456,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F2ef108bf-e3fd-4f74-82dd-cd82a457194a_1024x1536.png 1456w" sizes="auto, 100vw"><img src="iframe.php?url=https%3A%2F%2Fsubstackcdn.com%2Fimage%2Ffetch%2F%24s_%21cWjm%21%2Cw_1456%2Cc_limit%2Cf_auto%2Cq_auto%3Agood%2Cfl_progressive%3Asteep%2Fhttps%253A%252F%252Fsubstack-post-media.s3.amazonaws.com%252Fpublic%252Fimages%252F2ef108bf-e3fd-4f74-82dd-cd82a457194a_1024x1536.png" width="1024" height="1536" 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srcset="https://substackcdn.com/image/fetch/$s_!cWjm!,w_424,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F2ef108bf-e3fd-4f74-82dd-cd82a457194a_1024x1536.png 424w, https://substackcdn.com/image/fetch/$s_!cWjm!,w_848,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F2ef108bf-e3fd-4f74-82dd-cd82a457194a_1024x1536.png 848w, https://substackcdn.com/image/fetch/$s_!cWjm!,w_1272,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F2ef108bf-e3fd-4f74-82dd-cd82a457194a_1024x1536.png 1272w, https://substackcdn.com/image/fetch/$s_!cWjm!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F2ef108bf-e3fd-4f74-82dd-cd82a457194a_1024x1536.png 1456w" sizes="auto, 100vw" loading="lazy"></picture><div class="image-link-expand"><div class="pencraft pc-display-flex pc-gap-8 pc-reset"><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container restack-image buttonBase-GK1x3M"><svg aria-hidden="true" width="20" height="20" viewBox="0 0 20 20" fill="none" stroke-width="1.5" stroke="var(--color-fg-primary)" stroke-linecap="round" stroke-linejoin="round" xmlns="http://www.w3.org/2000/svg" class="icon-noB79L"><g><path d="M2.53001 7.81595C3.49179 4.73911 6.43281 2.5 9.91173 2.5C13.1684 2.5 15.9537 4.46214 17.0852 7.23684L17.6179 8.67647M17.6179 8.67647L18.5002 4.26471M17.6179 8.67647L13.6473 6.91176M17.4995 12.1841C16.5378 15.2609 13.5967 17.5 10.1178 17.5C6.86118 17.5 4.07589 15.5379 2.94432 12.7632L2.41165 11.3235M2.41165 11.3235L1.5293 15.7353M2.41165 11.3235L6.38224 13.0882"></path></g></svg></button><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container view-image buttonBase-GK1x3M"><svg xmlns="http://www.w3.org/2000/svg" width="20" height="20" viewBox="0 0 24 24" fill="none" stroke="currentColor" stroke-width="2" stroke-linecap="round" stroke-linejoin="round" class="lucide lucide-maximize2 lucide-maximize-2 icon-noB79L"><polyline points="15 3 21 3 21 9"></polyline><polyline points="9 21 3 21 3 15"></polyline><line x1="21" x2="14" y1="3" y2="10"></line><line x1="3" x2="10" y1="21" y2="14"></line></svg></button></div></div></div></a></figure></div><p>The idea of a curse is strangely comforting.</p><p>That may sound absurd, but think about it.</p><p>If a curse is responsible, then you are not.</p><p>If an evil force is responsible, then there is nothing you could have done differently.</p><p>If fate is responsible, then failure was inevitable.</p><p>The moment we assign responsibility to something outside ourselves, we also surrender power to something outside ourselves.</p><p>And that is where many people get stuck.</p><p>Years ago, I became fascinated by something people rarely discuss.</p><p>Not the dramatic stories.</p><p>The ordinary ones.</p><p>The families where the same mistakes seemed to repeat themselves for decades.</p><p>The father who never expressed affection.</p><p>His son grows up feeling unseen.</p><p>That son becomes a father himself.</p><p>He loves his children deeply but struggles to express it.</p><p>His children grow up feeling unseen.</p><p>Three generations.</p><p>Same wound.</p><p>Different faces.</p><p>Nobody planned it.</p><p>Nobody intended it.</p><p>Yet there it is.</p><p>A pattern so consistent that from a distance it begins to look supernatural.</p><p>Consider the family where every man drinks.</p><p>The grandfather drank.</p><p>The father drank.</p><p>The son drinks.</p><p>By the time the grandson starts drinking, someone eventually says:</p><p>&#8220;The men in this family are cursed.&#8221;</p><p>But let us ask a different question.</p><p>What if the grandson learned that alcohol is how men deal with pain?</p><p>What if every difficult emotion he ever witnessed was managed with a bottle?</p><p>What if nobody taught him another way?</p><p>The behaviour appears inevitable.</p><p>The outcome appears inevitable.</p><p>The pattern appears inevitable.</p><p>And inevitability is often mistaken for destiny.</p><p>The same thing happens with relationships.</p><p>A woman grows up watching her mother tolerate neglect, infidelity, disrespect, or emotional unavailability.</p><p>As a child, she hates it.</p><p>She promises herself she will never accept such treatment.</p><p>Then twenty years later she finds herself with a man who behaves exactly like the father she swore she would never marry.</p><p>People watching from the outside are bewildered.</p><p>She is bewildered.</p><p>How did this happen?</p><p>Because what we consciously reject and what we unconsciously normalize are often two different things.</p><p>Children do not simply inherit what their parents say.</p><p>They inherit what their parents demonstrate.</p><p>They inherit what their parents tolerate.</p><p>They inherit what their parents reward.</p><p>They inherit what their parents fear.</p><p>Most importantly, they inherit what their parents consider normal.</p><p>And normal is one of the most powerful forces on earth.</p><p>A child raised in chaos does not experience chaos as chaos.</p><p>They experience it as life.</p><p>A child raised around shouting does not necessarily see shouting as dysfunction.</p><p>They see it as communication.</p><p>A child raised around emotional neglect may spend decades confusing emotional neglect with love.</p><p>Because normal does not announce itself.</p><p>Normal simply becomes invisible.</p><p>This is why so many inherited patterns survive.</p><p>Nobody sees them.</p><p>People only see the outcome.</p><p>The failed marriage.</p><p>The addiction.</p><p>The debt.</p><p>The poverty.</p><p>The broken relationship.</p><p>The family conflict.</p><p>And because they cannot see the invisible forces producing the outcome, they search for another explanation.</p><p>A curse.</p><p>Bad luck.</p><p>Destiny.</p><p>Anything except the possibility that the pattern itself is the problem.</p><p>This is where the conversation becomes uncomfortable.</p><p>Because if inherited patterns exist, then every family must ask difficult questions.</p><p>What beliefs have we inherited without examining?</p><p>What fears have we inherited without challenging?</p><p>What habits have we inherited without questioning?</p><p>What stories have we inherited without testing?</p><p>What if the greatest inheritance many families pass down is not wealth or property, but assumptions?</p><p>Assumptions about money.</p><p>Assumptions about marriage.</p><p>Assumptions about success.</p><p>Assumptions about gender.</p><p>Assumptions about suffering.</p><p>Assumptions about what is possible.</p><p>And perhaps the most dangerous assumption of all:</p><p>&#8220;This is just how we are.&#8221;</p><p>Those six words have imprisoned generations.</p><p>Because the moment a pattern becomes identity, change becomes betrayal.</p><p>The person who challenges it becomes the problem.</p><p>The daughter who questions tradition becomes rebellious.</p><p>The son who refuses the family script becomes difficult.</p><p>The family member who chooses a different path becomes the outlier.</p><p>Every system resists change.</p><p>Even dysfunctional ones.</p><p>Especially dysfunctional ones.</p><p>And that is why patterns survive for generations.</p><p>Not because they are true.</p><p>Not because they are inevitable.</p><p>But because they are familiar.</p><p><em>And familiarity is often mistaken for truth.</em></p><p><strong>But perhaps the most important patterns are not behaviours.</strong></p><p>They are beliefs.</p><p>Because behaviours are visible.</p><p>Beliefs are not.</p><p>A man can see that he drinks too much.</p><p>It is harder to see that he believes vulnerability is weakness.</p><p>A woman can see that she keeps choosing the wrong partners.</p><p>It is harder to see that she believes love must be earned.</p><p>A family can see that they struggle financially.</p><p>It is harder to see that they have spent generations teaching their children that wealth belongs to other people.</p><p>This is where inherited patterns become truly dangerous.</p><p>Because most people do not inherit instructions.</p><p>They inherit assumptions.</p><p>Assumptions about what is normal.</p><p>Assumptions about what is possible.</p><p>Assumptions about who they are.</p><p>Assumptions about who they can become.</p><p>And assumptions are powerful because they rarely feel like beliefs.</p><p>They feel like reality.</p><p>A child grows up hearing:</p><p>&#8220;People like us don&#8217;t become rich.&#8221;</p><p>Nobody calls it a curse.</p><p>Yet thirty years later that child is turning down opportunities, avoiding risks, and sabotaging success without realizing why.</p><p>A boy grows up hearing:</p><p>&#8220;Men don&#8217;t cry.&#8221;</p><p>Nobody calls it a curse.</p><p>Yet forty years later he cannot express grief, intimacy, vulnerability, or love.</p><p>A girl grows up hearing:</p><p>&#8220;A good woman endures.&#8221;</p><p>Nobody calls it a curse.</p><p>Yet she spends twenty years tolerating things she should have walked away from long ago.</p><p>Different stories.</p><p>Same mechanism.</p><p>An inherited belief quietly shaping an entire life.</p><p>The older I get, the more convinced I become that the most powerful inheritance is not what your parents leave you.</p><p>It is what they teach you is normal.</p><p>Because normal becomes invisible.</p><p>And invisible things are difficult to challenge.</p><p>Think about it.</p><p>How many beliefs do you hold that you consciously chose?</p><p>How many opinions are truly yours?</p><p>How many fears belong to you?</p><p>How many ambitions belong to you?</p><p>How many of your convictions were carefully examined before you accepted them?</p><p>And how many simply arrived through repetition?</p><p>Family.</p><p>Religion.</p><p>Culture.</p><p>Community.</p><p>School.</p><p>Friends.</p><p>Tradition.</p><p>The voices around us become the voices within us.</p><p>Then one day we wake up and call those voices our identity.</p><p>That is why questioning inherited beliefs feels so uncomfortable.</p><p>It feels personal.</p><p>It feels disloyal.</p><p>It feels like betraying your family, your culture, your faith, your community, or your history.</p><p>But every generation faces the same choice.</p><p>Will I continue this pattern?</p><p>Or will I examine it?</p><p>Because not everything old is wisdom.</p><p>Not everything inherited is truth.</p><p>Not everything repeated deserves to survive.</p><p>Some traditions preserve life.</p><p>Others preserve suffering.</p><p>Some beliefs create freedom.</p><p>Others create prisons.</p><p>And one of the responsibilities of adulthood is learning the difference.</p><p>This is the point where many people become uncomfortable.</p><p>Because if inherited patterns are real, then some of the things we call destiny may actually be decisions.</p><p>Not conscious decisions.</p><p>Inherited decisions.</p><p>Repeated decisions.</p><p>Unquestioned decisions.</p><p>The kind that survive simply because nobody stopped long enough to ask:</p><p>&#8220;Why?&#8221;</p><p>And that question changes everything.</p><p>Because the moment you ask why, you begin to see the pattern.</p><p>The moment you see the pattern, you can interrupt it.</p><p>And the moment you interrupt it, something extraordinary happens.</p><p>What looked like fate begins to look like a choice.</p><p>What looked like a curse begins to look like a habit.</p><p>What looked like destiny begins to look like a story that can be rewritten.</p><p><em>And that realization may be one of the most liberating discoveries a human being can make.</em></p><p><strong>Perhaps some curses are real.</strong></p><p>Perhaps some things exist beyond our understanding.</p><p>I am humble enough to admit that human beings do not know everything.</p><p>But I am also convinced that many of the things we call curses are simply patterns that have survived long enough to become invisible.</p><p>Patterns of fear.</p><p>Patterns of addiction.</p><p>Patterns of poverty.</p><p>Patterns of silence.</p><p>Patterns of violence.</p><p>Patterns of self sabotage.</p><p>Patterns of belief.</p><p>Patterns passed from one generation to the next until nobody remembers where they began.</p><p>The tragedy is not that these patterns exist.</p><p>The tragedy is that many people mistake them for destiny.</p><p>They stop questioning them.</p><p>Stop challenging them.</p><p>Stop imagining another possibility.</p><p>And so the pattern continues.</p><p>Not because it is powerful.</p><p>But because it is familiar.</p><p>That is why responsibility matters.</p><p>Not responsibility for what happened to you.</p><p>Not responsibility for the family you were born into.</p><p>Not responsibility for the beliefs you inherited as a child.</p><p>A child does not choose those things.</p><p>But every adult eventually faces a different question.</p><p>What will I do with them?</p><p>Because there comes a moment in every life when inheritance becomes choice.</p><p>You can continue the pattern.</p><p>Or interrupt it.</p><p>You can pass it on.</p><p>Or let it end with you.</p><p>You can teach your children the same fears.</p><p>Or teach them courage.</p><p>You can hand down the same wounds.</p><p>Or begin the work of healing them.</p><p>The older I get, the less interested I become in assigning blame.</p><p>And the more interested I become in understanding responsibility.</p><p>Blame looks backward.</p><p>Responsibility looks forward.</p><p>Blame asks:</p><p>&#8220;Whose fault is this?&#8221;</p><p>Responsibility asks:</p><p>&#8220;What do we do now?&#8221;</p><p>And perhaps that is the most important question of all.</p><p>Not whether your family was cursed.</p><p>Not whether your ancestors got something wrong.</p><p>Not whether life has treated you unfairly.</p><p>But whether you are willing to become the person who breaks the pattern.</p><p>Because the opposite of a curse is not a miracle.</p><p>The opposite of a curse is awareness.</p><p>The moment you can see a pattern, you can challenge it.</p><p>The moment you can challenge it, you can change it.</p><p>And the moment you change it, what looked like destiny becomes a decision.</p><p>Perhaps that is what healing really is.</p><p>Not escaping your inheritance.</p><p>But refusing to pass on everything you received.</p><p>And maybe that is how curses end.</p><p>Not with deliverance.</p><p><em><strong>But with someone deciding that it stops here.</strong></em></p><p>If this article resonated with you, share it with someone who may need to read it.</p><p>Someone trying to understand their family.</p><p>Someone trying to understand themselves.</p><p>Someone carrying a pattern they have mistaken for destiny.</p><p>And if these are the kinds of conversations you wish more people were having, subscribe and join us.</p><p>The Diary of a Playboy is a space for exploring the hidden forces that shape our relationships, decisions, families, careers, beliefs, and lives.</p><p>Finally, if this piece made you pause, reflect, question an old assumption, or see your story differently, consider buying the author a coffee.</p><p>It helps support the writing and keeps these conversations alive.</p><p>Until next time,</p><p><strong>Martins</strong></p><p><em>The Diary of a Playboy</em></p><div class="subscription-widget-wrap-editor" data-attrs="{&quot;url&quot;:&quot;https://thediaryofaplayboy.substack.com/subscribe?&quot;,&quot;text&quot;:&quot;Subscribe&quot;,&quot;language&quot;:&quot;en&quot;}" data-component-name="SubscribeWidgetToDOM"><div class="subscription-widget show-subscribe"><div class="preamble"><p class="cta-caption">The Diary of a Playboy is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.</p></div><form class="subscription-widget-subscribe"><input type="email" class="email-input" name="email" placeholder="Type your email&#8230;" tabindex="-1"><input type="submit" class="button primary" value="Subscribe"><div class="fake-input-wrapper"><div class="fake-input"></div><div class="fake-button"></div></div></form></div></div>]]></content:encoded></item><item><title><![CDATA[Why Smart People Stay Where They Are Unhappy]]></title><description><![CDATA[The hidden forces that keep intelligent people trapped in relationships they know are hurting them.]]></description><link>https://thediaryofaplayboy.substack.com/p/why-smart-people-stay-where-they</link><guid isPermaLink="false">https://thediaryofaplayboy.substack.com/p/why-smart-people-stay-where-they</guid><dc:creator><![CDATA[Martins Itua]]></dc:creator><pubDate>Thu, 11 Jun 2026 17:10:08 GMT</pubDate><enclosure url="iframe.php?url=https%3A%2F%2Fsubstackcdn.com%2Fimage%2Ffetch%2F%24s_%21l5mY%21%2Cf_auto%2Cq_auto%3Agood%2Cfl_progressive%3Asteep%2Fhttps%253A%252F%252Fsubstack-post-media.s3.amazonaws.com%252Fpublic%252Fimages%252Ff07baed0-3ffc-436b-a3f5-f5ba036e576e_1024x1536.png" length="0" type="image/jpeg"/><content:encoded><![CDATA[<p>A woman sat across from me one evening and described, in extraordinary detail, how her boyfriend manipulated her.</p><p>She knew when he was lying.</p><div class="subscription-widget-wrap-editor" data-attrs="{&quot;url&quot;:&quot;https://thediaryofaplayboy.substack.com/subscribe?&quot;,&quot;text&quot;:&quot;Subscribe&quot;,&quot;language&quot;:&quot;en&quot;}" data-component-name="SubscribeWidgetToDOM"><div class="subscription-widget show-subscribe"><div class="preamble"><p class="cta-caption">The Diary of a Playboy is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.</p></div><form class="subscription-widget-subscribe"><input type="email" class="email-input" name="email" placeholder="Type your email&#8230;" tabindex="-1"><input type="submit" class="button primary" value="Subscribe"><div class="fake-input-wrapper"><div class="fake-input"></div><div class="fake-button"></div></div></form></div></div><p>She knew when he was gaslighting her.</p><p>She knew when he was trying to make her doubt her own memory.</p><p>She knew he had cheated before.</p><p>She knew he would probably cheat again.</p><p>She knew her friends disliked him.</p><p>She knew her family wanted her to leave.</p><p>She knew she was unhappy.</p><p>Then she looked at me and said something I have never forgotten.</p><p>&#8220;I know all of that. So why can&#8217;t I leave?&#8221;</p><p>It is one of the most fascinating questions in human behaviour.</p><p>Because the woman was not stupid.</p><p>Far from it.</p><p>She had a graduate degree.</p><p>A successful career.</p><p>She managed teams, negotiated contracts, solved complex problems, and made decisions affecting hundreds of people every day.</p><p>Yet she could not explain why she remained in a relationship that was slowly destroying her peace.</p><p>And she is not alone.</p><p>Some of the smartest people you will ever meet are trapped in the worst relationships.</p><p>Doctors.</p><p>Lawyers.</p><p>Professors.</p><p>Entrepreneurs.</p><p>Executives.</p><p>People capable of solving problems that would intimidate most of us.</p><p>Yet somehow unable to solve the one unfolding in their own lives.</p><p>For years, I believed intelligence protected people from bad decisions.</p><p>Then I started paying attention.</p><p>What I discovered changed how I think about relationships forever.</p><p>Because people rarely stay in bad relationships for the reasons outsiders imagine.</p><p>It is usually not weakness.</p><p>It is usually not stupidity.</p><p>And it is almost never as simple as love.</p><p>The real reasons are far more uncomfortable.</p><p>And if we are honest, many of us will recognize ourselves in them.</p><div class="captioned-image-container"><figure><a class="image-link image2 is-viewable-img" target="_blank" href="iframe.php?url=https%3A%2F%2Fsubstackcdn.com%2Fimage%2Ffetch%2F%24s_%21l5mY%21%2Cf_auto%2Cq_auto%3Agood%2Cfl_progressive%3Asteep%2Fhttps%253A%252F%252Fsubstack-post-media.s3.amazonaws.com%252Fpublic%252Fimages%252Ff07baed0-3ffc-436b-a3f5-f5ba036e576e_1024x1536.png" data-component-name="Image2ToDOM"><div class="image2-inset"><picture><source type="image/webp" 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class="image-link-expand"><div class="pencraft pc-display-flex pc-gap-8 pc-reset"><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container restack-image buttonBase-GK1x3M"><svg aria-hidden="true" width="20" height="20" viewBox="0 0 20 20" fill="none" stroke-width="1.5" stroke="var(--color-fg-primary)" stroke-linecap="round" stroke-linejoin="round" xmlns="http://www.w3.org/2000/svg" class="icon-noB79L"><g><path d="M2.53001 7.81595C3.49179 4.73911 6.43281 2.5 9.91173 2.5C13.1684 2.5 15.9537 4.46214 17.0852 7.23684L17.6179 8.67647M17.6179 8.67647L18.5002 4.26471M17.6179 8.67647L13.6473 6.91176M17.4995 12.1841C16.5378 15.2609 13.5967 17.5 10.1178 17.5C6.86118 17.5 4.07589 15.5379 2.94432 12.7632L2.41165 11.3235M2.41165 11.3235L1.5293 15.7353M2.41165 11.3235L6.38224 13.0882"></path></g></svg></button><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container view-image buttonBase-GK1x3M"><svg xmlns="http://www.w3.org/2000/svg" width="20" height="20" viewBox="0 0 24 24" fill="none" stroke="currentColor" stroke-width="2" stroke-linecap="round" stroke-linejoin="round" class="lucide lucide-maximize2 lucide-maximize-2 icon-noB79L"><polyline points="15 3 21 3 21 9"></polyline><polyline points="9 21 3 21 3 15"></polyline><line x1="21" x2="14" y1="3" y2="10"></line><line x1="3" x2="10" y1="21" y2="14"></line></svg></button></div></div></div></a></figure></div><p>The obvious answer is love.</p><p>That is what most people assume.</p><p>They stay because they love the person.</p><p>But love explains far less than we think.</p><p>After all, many people leave relationships they still love.</p><p>And many people remain in relationships that make them miserable.</p><p>So if love is not the whole story, what is?</p><p>Over the years, I have come to believe that people stay for reasons they often do not fully understand themselves.</p><p>The relationship becomes a meeting point for childhood wounds, fears, hopes, identities, habits, expectations, and emotional needs.</p><p>From the outside, the decision makes no sense.</p><p>From the inside, it often feels inevitable.</p><p>The hidden forces are rarely obvious.</p><p>But once you see them, you begin to understand why so many intelligent people remain trapped in relationships they know are hurting them.</p><p>The first clue is something most people mistake for chemistry.</p><p>A woman once told me she had spent twenty years dating the same man.</p><p>Not literally.</p><p>The names were different.</p><p>The faces were different.</p><p>The careers were different.</p><p>But the relationship was always the same.</p><p>The men were emotionally distant.</p><p>Difficult to read.</p><p>Difficult to reach.</p><p>Generous with attention one week and unavailable the next.</p><p>Every relationship left her feeling as though she had to earn love instead of simply receiving it.</p><p>For years she blamed bad luck.</p><p>Then one day she said something that stopped me.</p><p>&#8220;My father loved me,&#8221; she said. &#8220;But I spent my entire childhood trying to get his attention.&#8221;</p><p>Her father was not abusive.</p><p>He worked hard.</p><p>Provided for the family.</p><p>Showed up when it mattered.</p><p>But emotionally, he lived somewhere she could never quite reach.</p><p>And without realizing it, she spent the next twenty years choosing men who felt exactly the same way.</p><p>Not because she wanted pain.</p><p>Because she recognized it.</p><p>There is a difference.</p><p>One of the most uncomfortable truths about human beings is that we are not always attracted to what is healthy.</p><p>We are often attracted to what feels familiar.</p><p>Even when familiarity hurts us.</p><p>A person raised around criticism may feel strangely uncomfortable with kindness.</p><p>A person raised around emotional distance may mistake emotional distance for strength.</p><p>A person who spent childhood earning affection may spend adulthood earning it again and again.</p><p>What outsiders call a bad relationship often feels completely normal to the person inside it.</p><p>That is why intelligence is not enough.</p><p>Logic can identify a pattern.</p><p>It cannot always break one.</p><p>Especially when the pattern feels like home.</p><p>And home is a powerful thing.</p><p>Even when it hurts.</p><p>Perhaps especially when it hurts.</p><p>But familiarity is only part of the story.</p><p>If it were the whole story, people would leave the moment they recognized the pattern.</p><p>Most don&#8217;t.</p><p>Because another force quietly enters the relationship.</p><p>Hope.</p><p>Hope is one of the most beautiful things human beings possess.</p><p>It is also one of the most dangerous.</p><p>A man lies.</p><p>He apologizes.</p><p>Things improve for a while.</p><p>A woman feels neglected.</p><p>She finally raises the issue.</p><p>For a few weeks, her partner becomes attentive again.</p><p>A husband cheats.</p><p>His wife discovers it.</p><p>He cries.</p><p>Promises change.</p><p>Becomes the man she always wanted him to be.</p><p>For three months.</p><p>Then six.</p><p>Then the old behaviour returns.</p><p>People often imagine bad relationships as a constant state of misery.</p><p>Most are not.</p><p>If they were, leaving would be easier.</p><p>The problem is that unhealthy relationships often contain just enough happiness to keep hope alive.</p><p>The good days become evidence.</p><p>The apologies become evidence.</p><p>The promises become evidence.</p><p>The brief moments of tenderness become evidence.</p><p>Evidence that things are changing.</p><p>Evidence that the person you need them to become is finally emerging.</p><p>And so people stay.</p><p>Not because of who their partner is.</p><p>But because of who they believe their partner could become.</p><p>I have seen intelligent people spend years in relationships with potential.</p><p>Potential is seductive.</p><p>Potential asks for patience.</p><p>Potential asks for understanding.</p><p>Potential asks for one more chance.</p><p>Potential always lives in the future.</p><p>The problem is that relationships are lived in the present.</p><p>One woman told me she stayed with a man for twelve years because she knew what he was capable of becoming.</p><p>Twelve years.</p><p>Imagine spending twelve years loving someone&#8217;s future while being neglected by their present.</p><p>Eventually she realized something painful.</p><p>She was in a relationship with a version of him that existed only in her imagination.</p><p>And she is not alone.</p><p>Many people are not dating who is standing in front of them.</p><p>They are dating a possibility.</p><p>A prediction.</p><p>A dream.</p><p>And dreams are very difficult to break up with.</p><p>Then there is another force people rarely talk about.</p><p>Fear.</p><p>Not fear of the relationship.</p><p>Fear of life after the relationship.</p><p>Leaving sounds courageous in theory.</p><p>In reality, it can feel terrifying.</p><p>Especially when you have invested years.</p><p>Sometimes decades.</p><p>A woman in her forties wonders whether she will ever find love again.</p><p>A man in his fifties wonders whether starting over is worth it.</p><p>Someone else worries about their children.</p><p>Someone worries about finances.</p><p>Someone worries about loneliness.</p><p>Someone worries about becoming the person everyone whispers about at family gatherings.</p><p>The fear is not always visible.</p><p>But it sits quietly in the background.</p><p>Influencing decisions.</p><p>Shaping behaviour.</p><p>Convincing people to remain where they are unhappy because uncertainty feels even worse.</p><p>I once met a man who admitted something most people are unwilling to say out loud.</p><p>&#8220;I am not staying because I&#8217;m happy,&#8221; he said.</p><p>&#8220;I&#8217;m staying because I don&#8217;t know who I am without this relationship.&#8221;</p><p>That sentence stayed with me.</p><p>Because for many people, relationships become identities.</p><p>You are no longer simply yourself.</p><p>You become someone&#8217;s husband.</p><p>Someone&#8217;s wife.</p><p>Someone&#8217;s partner.</p><p>Someone&#8217;s future.</p><p>Someone&#8217;s family.</p><p>The relationship becomes woven into your sense of self.</p><p>And when that happens, leaving feels less like ending a relationship and more like losing part of your identity.</p><p>People talk about heartbreak.</p><p>They rarely talk about identity loss.</p><p>But identity loss can be just as devastating.</p><p>Who are you if the relationship ends?</p><p>Who are you if the future you imagined disappears?</p><p>Who are you if the role you built your life around no longer exists?</p><p>Those questions frighten people.</p><p>Sometimes enough to keep them where they are.</p><p>Which brings us to perhaps the most uncomfortable truth of all.</p><p>Intelligence is not always a solution.</p><p>Sometimes it becomes part of the problem.</p><p>Because intelligent people are exceptionally good at explaining things.</p><p>Explaining behaviour.</p><p>Explaining mistakes.</p><p>Explaining patterns.</p><p>Explaining why someone acted the way they did.</p><p>Explaining why things will be different next time.</p><p>Explaining why they should stay.</p><p>A friend once described this perfectly.</p><p>He said some people become defence attorneys for the people hurting them.</p><p>They build brilliant cases.</p><p>Present compelling arguments.</p><p>Identify mitigating circumstances.</p><p>Explain the childhood trauma.</p><p>Explain the stress.</p><p>Explain the pressure.</p><p>Explain everything except the simple fact that they are unhappy.</p><p>The truth is that intelligence helps us understand behaviour.</p><p>But understanding behaviour is not the same as changing it.</p><p>You can understand exactly why someone hurts you and still keep giving them access to your life.</p><p>You can recognize every red flag and still stay.</p><p>You can see the pattern and still repeat it.</p><p>Because relationships are not governed by logic alone.</p><p>They are governed by attachment.</p><p>Memory.</p><p>Identity.</p><p>Fear.</p><p>Hope.</p><p>History.</p><p>And all the invisible forces that make human beings wonderfully complicated and occasionally self destructive.</p><p>Which is why some of the smartest people you will ever meet remain trapped in relationships that everyone else can see are hurting them.</p><p>Not because they cannot see the problem.</p><p>But because seeing the problem is often the easiest part.</p><p>The harder question is this:</p><p>If the relationship ended tomorrow, what part of you would have to change with it?</p><p>And that is the question many people spend years avoiding.</p><p>At this point, it is tempting to think this article is about relationships.</p><p>It isn&#8217;t.</p><p>At least not entirely.</p><p>Relationships are simply where these hidden forces become visible.</p><p>The real story is much bigger.</p><p>A woman spends twenty years chasing emotionally unavailable men.</p><p>A man spends twenty years trying to earn the approval of people who will never give it.</p><p>Someone stays in a miserable job because they are afraid to start over.</p><p>Someone else remains trapped in a friendship that no longer serves them.</p><p>Another spends years trying to prove their worth through money, success, status, or achievement.</p><p>Different situations.</p><p>Same pattern.</p><p>The human being is remarkably consistent.</p><p>We keep returning to unfinished business.</p><p>Not consciously.</p><p>But relentlessly.</p><p>The woman who keeps choosing unavailable partners may not be searching for love.</p><p>She may be trying to finally receive the affection she never received as a child.</p><p>The man obsessed with success may not be chasing wealth.</p><p>He may be chasing validation.</p><p>The employee who cannot leave a toxic workplace may not be afraid of unemployment.</p><p>They may be afraid of discovering who they are without the title.</p><p>The relationship is rarely the relationship.</p><p>The job is rarely the job.</p><p>The money is rarely the money.</p><p>Beneath almost every recurring struggle is a deeper question trying to be answered.</p><p>Am I enough?</p><p>Am I lovable?</p><p>Am I worthy?</p><p>Do I matter?</p><p>Will someone choose me?</p><p>Will someone stay?</p><p>Most people spend their lives trying to answer those questions through other people.</p><p>Through relationships.</p><p>Through careers.</p><p>Through achievement.</p><p>Through sacrifice.</p><p>Through approval.</p><p>Through status.</p><p>Through being needed.</p><p>Through being wanted.</p><p>The tragedy is that no person can permanently answer a question that was never theirs to answer in the first place.</p><p>That is why intelligent people often remain stuck.</p><p>They are trying to solve an emotional problem with a logical mind.</p><p>Trying to solve a childhood wound with an adult relationship.</p><p>Trying to solve a self worth problem with another person&#8217;s behaviour.</p><p>And no relationship can carry that weight forever.</p><p>The moment I understood this, I started seeing people differently.</p><p>The woman staying with a man who repeatedly disappoints her.</p><p>The executive who cannot walk away from a career that is destroying his health.</p><p>The friend who keeps returning to people who only call when they need something.</p><p>The parent desperately trying to earn love from children who have already grown distant.</p><p>All of them are asking some version of the same question.</p><p>Not:</p><p>&#8220;Should I stay?&#8221;</p><p>But:</p><p>&#8220;What am I really afraid of losing if I leave?&#8221;</p><p>And that question changes everything.</p><p>Because sometimes the answer is not the person.</p><p>Sometimes it is the hope.</p><p>The identity.</p><p>The dream.</p><p>The future you imagined.</p><p>The wound you hoped they would heal.</p><p>And once you see that, you are no longer looking at a relationship.</p><p>You are looking at yourself.</p><p>The woman from the beginning of this article was asking the wrong question.</p><p>Not because she lacked intelligence.</p><p>Because most of us ask the wrong question.</p><p>We ask:</p><p>&#8220;Why can&#8217;t I leave?&#8221;</p><p>When perhaps the better question is:</p><p>&#8220;What is keeping me here?&#8221;</p><p>Those are not the same question.</p><p>One focuses on the relationship.</p><p>The other focuses on the hidden forces beneath it.</p><p>And that distinction changes everything.</p><p>Because the day you identify what is really keeping you there is the day you begin to reclaim your freedom.</p><p>Sometimes it is love.</p><p>But often it is fear.</p><p>Fear of loneliness.</p><p>Fear of failure.</p><p>Fear of starting over.</p><p>Fear of discovering that the future you imagined is never coming.</p><p>Sometimes it is hope.</p><p>Hope that this time will be different.</p><p>Hope that they will finally change.</p><p>Hope that one more conversation, one more chance, one more year will somehow produce a different outcome.</p><p>Sometimes it is identity.</p><p>You have spent so many years being someone&#8217;s partner that you no longer know who you are without them.</p><p>And sometimes it is something even deeper.</p><p>The quiet belief that if this person finally loves you the way you need to be loved, it will somehow heal something much older.</p><p>Something they did not create.</p><p>And something they were never capable of fixing.</p><p>That realization can be painful.</p><p>But it can also be liberating.</p><p>Because once you understand what is really happening, you stop making decisions from confusion.</p><p>You stop calling familiarity love.</p><p>You stop calling hope evidence.</p><p>You stop calling fear commitment.</p><p>You stop calling self abandonment loyalty.</p><p>And you begin to see the relationship for what it is.</p><p>Not what you wish it would become.</p><p>Not what it once was.</p><p>Not what it promises to be.</p><p>What it is.</p><p>Today.</p><p>Right now.</p><p>In this moment.</p><p>The truth is that intelligent people do not stay in bad relationships because they are unintelligent.</p><p>They stay because they are human.</p><p>And being human means carrying history into the present.</p><p>It means dragging old wounds into new relationships.</p><p>It means mistaking familiar pain for destiny.</p><p>It means believing that if we can just solve one more puzzle, endure one more disappointment, love a little harder, sacrifice a little more, everything will finally make sense.</p><p>Sometimes it does.</p><p>Often it doesn&#8217;t.</p><p>The hardest lesson adulthood teaches is that not every wound can be healed by another person.</p><p>Some wounds require understanding.</p><p>Some require acceptance.</p><p>Some require boundaries.</p><p>And some require letting go.</p><p>So let me leave you with the same question I wish someone had asked the woman at the beginning of this story.</p><p>If this relationship ended tomorrow, what would you actually lose?</p><p>The person?</p><p>Or the hope?</p><p>The identity?</p><p>The dream?</p><p>The future you imagined?</p><p>The wound you hoped they would heal?</p><p>Sit with that question.</p><p>Because your answer may reveal more about your life than your relationship.</p><p>If this article resonated with you, share it with someone who may need to read it.</p><p>And if these are the kinds of conversations you wish more people were having, subscribe and join us.</p><p>Until next time,</p><p><strong>Martins</strong></p><p>The Diary of a Playboy</p><p><em><strong>P.S. If this piece made you pause, reflect, or see yourself a little more clearly, consider buying the author a coffee. It helps keep these conversations alive.</strong></em></p><div class="subscription-widget-wrap-editor" data-attrs="{&quot;url&quot;:&quot;https://thediaryofaplayboy.substack.com/subscribe?&quot;,&quot;text&quot;:&quot;Subscribe&quot;,&quot;language&quot;:&quot;en&quot;}" data-component-name="SubscribeWidgetToDOM"><div class="subscription-widget show-subscribe"><div class="preamble"><p class="cta-caption">The Diary of a Playboy is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.</p></div><form class="subscription-widget-subscribe"><input type="email" class="email-input" name="email" placeholder="Type your email&#8230;" tabindex="-1"><input type="submit" class="button primary" value="Subscribe"><div class="fake-input-wrapper"><div class="fake-input"></div><div class="fake-button"></div></div></form></div></div>]]></content:encoded></item><item><title><![CDATA[10 Dating Rules for Women Over 35]]></title><description><![CDATA[She sat in her car staring at the restaurant entrance.]]></description><link>https://thediaryofaplayboy.substack.com/p/10-dating-rules-for-women-over-35</link><guid isPermaLink="false">https://thediaryofaplayboy.substack.com/p/10-dating-rules-for-women-over-35</guid><dc:creator><![CDATA[Martins Itua]]></dc:creator><pubDate>Sat, 06 Jun 2026 19:09:26 GMT</pubDate><enclosure url="iframe.php?url=https%3A%2F%2Fsubstackcdn.com%2Fimage%2Ffetch%2F%24s_%21_KB-%21%2Cf_auto%2Cq_auto%3Agood%2Cfl_progressive%3Asteep%2Fhttps%253A%252F%252Fsubstack-post-media.s3.amazonaws.com%252Fpublic%252Fimages%252F3231908f-1b5a-4027-b612-581a9a09b805_1024x1536.png" length="0" type="image/jpeg"/><content:encoded><![CDATA[<p>She sat in her car staring at the restaurant entrance.</p><p>It was only a date.</p><div class="subscription-widget-wrap-editor" data-attrs="{&quot;url&quot;:&quot;https://thediaryofaplayboy.substack.com/subscribe?&quot;,&quot;text&quot;:&quot;Subscribe&quot;,&quot;language&quot;:&quot;en&quot;}" data-component-name="SubscribeWidgetToDOM"><div class="subscription-widget show-subscribe"><div class="preamble"><p class="cta-caption">The Diary of a Playboy is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.</p></div><form class="subscription-widget-subscribe"><input type="email" class="email-input" name="email" placeholder="Type your email&#8230;" tabindex="-1"><input type="submit" class="button primary" value="Subscribe"><div class="fake-input-wrapper"><div class="fake-input"></div><div class="fake-button"></div></div></form></div></div><p>At least that is what she kept telling herself.</p><p>Ten years earlier, she would have walked in without thinking twice. But ten years earlier, she was married.</p><p>Ten years earlier, she believed she had already found her person.</p><p>Now she was 43.</p><p>Divorced.</p><p>A mother of two.</p><p>And sitting alone in a parking lot wondering whether she still remembered how to date.</p><p>The last few years had been consumed by survival.</p><p>School runs.</p><p>Work.</p><p>Bills.</p><p>Lawyers.</p><p>Heartbreak.</p><p>Learning how to sleep alone.</p><p>Learning how to stop checking her phone.</p><p>Learning how to stop wondering what she could have done differently.</p><p>A friend had finally convinced her to try again.</p><p>&#8220;Just one date,&#8221; her friend had said.</p><p>&#8220;What is the worst that could happen?&#8221;</p><p>Now, as she checked her reflection in the rearview mirror for the fifth time, she realized exactly what could happen.</p><p>Hope.</p><p>Hope was the dangerous thing.</p><p>The man seemed kind.</p><p>They had spoken for weeks.</p><p>He was funny.</p><p>Attentive.</p><p>Consistent.</p><p>For the first time in years, she found herself looking forward to hearing from someone.</p><p>Then her phone buzzed.</p><p>&#8220;Running a little late.&#8221;</p><p>Twenty minutes later, another message arrived.</p><p>&#8220;So sorry. Something came up. Rain check?&#8221;</p><p>She stared at the screen.</p><p>No explanation.</p><p>No phone call.</p><p>No attempt to reschedule.</p><p>Nothing.</p><p>She put the phone down.</p><p>Started the engine.</p><p>And drove home.</p><p>The tears surprised her.</p><p>Not because a stranger had stood her up.</p><p>But because she had finally found the courage to try again.</p><p>And life had reminded her why she had stopped.</p><p>The truth is that dating after 35 is different.</p><p>Not because older women are less attractive.</p><p>Not because there are no good men left.</p><p>And not because love becomes impossible.</p><p>Dating is different because the stakes are higher.</p><p>At 22, a bad relationship might cost you a year.</p><p>At 42, it can cost you peace.</p><p>Your finances.</p><p>Your children.</p><p>Your confidence.</p><p>Your ability to trust again.</p><p>Many women over 35 are not entering the dating world for the first time.</p><p>They are returning to it.</p><p>After divorce.</p><p>After widowhood.</p><p>After betrayal.</p><p>After years spent building careers, raising children, caring for family members, and creating lives that no longer revolve around romance.</p><p>The world they left no longer exists.</p><p>People meet through apps instead of introductions.</p><p>Conversations happen through screens instead of across tables.</p><p>Ghosting has replaced honesty.</p><p>And many people are more connected than ever while feeling more alone than ever.</p><p>That is why this article is not about finding a man.</p><p>It is about protecting your peace while remaining open to love.</p><p>It is about avoiding mistakes that cost years.</p><p>It is about recognizing the difference between attention and commitment, chemistry and compatibility, loneliness and love.</p><p>Most importantly, it is about understanding that starting over is not failure.</p><p>Sometimes it is wisdom.</p><p>And if you are going to start again, you might as well do it with your eyes open.</p><div class="captioned-image-container"><figure><a class="image-link image2 is-viewable-img" target="_blank" href="iframe.php?url=https%3A%2F%2Fsubstackcdn.com%2Fimage%2Ffetch%2F%24s_%21_KB-%21%2Cf_auto%2Cq_auto%3Agood%2Cfl_progressive%3Asteep%2Fhttps%253A%252F%252Fsubstack-post-media.s3.amazonaws.com%252Fpublic%252Fimages%252F3231908f-1b5a-4027-b612-581a9a09b805_1024x1536.png" data-component-name="Image2ToDOM"><div class="image2-inset"><picture><source type="image/webp" srcset="https://substackcdn.com/image/fetch/$s_!_KB-!,w_424,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F3231908f-1b5a-4027-b612-581a9a09b805_1024x1536.png 424w, https://substackcdn.com/image/fetch/$s_!_KB-!,w_848,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F3231908f-1b5a-4027-b612-581a9a09b805_1024x1536.png 848w, https://substackcdn.com/image/fetch/$s_!_KB-!,w_1272,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F3231908f-1b5a-4027-b612-581a9a09b805_1024x1536.png 1272w, https://substackcdn.com/image/fetch/$s_!_KB-!,w_1456,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F3231908f-1b5a-4027-b612-581a9a09b805_1024x1536.png 1456w" sizes="auto, 100vw"><img src="iframe.php?url=https%3A%2F%2Fsubstackcdn.com%2Fimage%2Ffetch%2F%24s_%21_KB-%21%2Cw_1456%2Cc_limit%2Cf_auto%2Cq_auto%3Agood%2Cfl_progressive%3Asteep%2Fhttps%253A%252F%252Fsubstack-post-media.s3.amazonaws.com%252Fpublic%252Fimages%252F3231908f-1b5a-4027-b612-581a9a09b805_1024x1536.png" width="1024" height="1536" 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srcset="https://substackcdn.com/image/fetch/$s_!_KB-!,w_424,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F3231908f-1b5a-4027-b612-581a9a09b805_1024x1536.png 424w, https://substackcdn.com/image/fetch/$s_!_KB-!,w_848,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F3231908f-1b5a-4027-b612-581a9a09b805_1024x1536.png 848w, https://substackcdn.com/image/fetch/$s_!_KB-!,w_1272,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F3231908f-1b5a-4027-b612-581a9a09b805_1024x1536.png 1272w, https://substackcdn.com/image/fetch/$s_!_KB-!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F3231908f-1b5a-4027-b612-581a9a09b805_1024x1536.png 1456w" sizes="auto, 100vw" loading="lazy"></picture><div class="image-link-expand"><div class="pencraft pc-display-flex pc-gap-8 pc-reset"><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container restack-image buttonBase-GK1x3M"><svg aria-hidden="true" width="20" height="20" viewBox="0 0 20 20" fill="none" stroke-width="1.5" stroke="var(--color-fg-primary)" stroke-linecap="round" stroke-linejoin="round" xmlns="http://www.w3.org/2000/svg" class="icon-noB79L"><g><path d="M2.53001 7.81595C3.49179 4.73911 6.43281 2.5 9.91173 2.5C13.1684 2.5 15.9537 4.46214 17.0852 7.23684L17.6179 8.67647M17.6179 8.67647L18.5002 4.26471M17.6179 8.67647L13.6473 6.91176M17.4995 12.1841C16.5378 15.2609 13.5967 17.5 10.1178 17.5C6.86118 17.5 4.07589 15.5379 2.94432 12.7632L2.41165 11.3235M2.41165 11.3235L1.5293 15.7353M2.41165 11.3235L6.38224 13.0882"></path></g></svg></button><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container view-image buttonBase-GK1x3M"><svg xmlns="http://www.w3.org/2000/svg" width="20" height="20" viewBox="0 0 24 24" fill="none" stroke="currentColor" stroke-width="2" stroke-linecap="round" stroke-linejoin="round" class="lucide lucide-maximize2 lucide-maximize-2 icon-noB79L"><polyline points="15 3 21 3 21 9"></polyline><polyline points="9 21 3 21 3 15"></polyline><line x1="21" x2="14" y1="3" y2="10"></line><line x1="3" x2="10" y1="21" y2="14"></line></svg></button></div></div></div></a></figure></div><h2>Rule 1: Do Not Date Potential</h2><p>At 27, a woman can afford to fall in love with potential.</p><p>At 37, she cannot.</p><p>I once met a woman who spent seven years waiting for a man to become who he promised he would be.</p><p>Every year brought a new explanation.</p><p>He was starting a business.</p><p>He was finding himself.</p><p>He was not ready.</p><p>He was working through something.</p><p>He just needed more time.</p><p>By the time she realized she had fallen in love with a future version of him that did not exist, she was 42.</p><p>Potential is one of the most expensive addictions in the dating world.</p><p>Date who people are.</p><p>Not who they might become.</p><p>Not who they were.</p><p>Not who they say they will be.</p><p>Who they are.</p><p>Today.</p><h2>Rule 2: Never Let Loneliness Choose for You</h2><p>Loneliness is one of the worst matchmakers on earth.</p><p>A widow once told me that after losing her husband, the silence became unbearable.</p><p>She missed having someone to talk to.</p><p>Someone to eat with.</p><p>Someone to call.</p><p>When she eventually met a man who gave her attention, she convinced herself she was falling in love.</p><p>She wasn&#8217;t.</p><p>She was falling in relief.</p><p>There is a difference.</p><p>Love says, &#8220;I choose you.&#8221;</p><p>Loneliness says, &#8220;Anyone will do.&#8221;</p><p>Many women over 35 are not looking for love.</p><p>They are looking for relief.</p><p>Be careful.</p><p>The two can feel remarkably similar in the beginning.</p><h2>Rule 3: Chemistry Is Overrated</h2><p>Chemistry is exciting.</p><p>Compatibility is useful.</p><p>One starts relationships.</p><p>The other sustains them.</p><p>A woman once described a man as &#8220;the most exciting person I have ever met.&#8221;</p><p>The relationship lasted eighteen months.</p><p>Every week contained drama.</p><p>Jealousy.</p><p>Arguments.</p><p>Breakups.</p><p>Reconciliations.</p><p>Passion.</p><p>Chaos.</p><p>She thought she was in love.</p><p>What she was actually experiencing was emotional volatility.</p><p>The man she eventually married was different.</p><p>Less exciting.</p><p>More dependable.</p><p>More consistent.</p><p>More peaceful.</p><p>&#8220;With him,&#8221; she said, &#8220;I sleep better.&#8221;</p><p>Never underestimate the value of sleeping peacefully.</p><h2>Rule 4: Watch How They Handle Disappointment</h2><p>Anyone can be charming when life is going well.</p><p>The real person appears when things do not go their way.</p><p>Pay attention to how they treat waiters.</p><p>How they speak about exes.</p><p>How they handle rejection.</p><p>How they react when frustrated.</p><p>How they behave when nobody is watching.</p><p>Character reveals itself under pressure.</p><p>Charm does not.</p><h2>Rule 5: Do Not Ignore Red Flags Because Time Is Running Out</h2><p>Many women over 35 feel a quiet pressure.</p><p>Some want marriage.</p><p>Some want companionship.</p><p>Some want children.</p><p>Some simply do not want to start over again.</p><p>That pressure can become dangerous.</p><p>It causes people to negotiate with reality.</p><p>&#8220;He isn&#8217;t perfect.&#8221;</p><p>&#8220;Nobody is perfect.&#8221;</p><p>&#8220;He&#8217;ll change.&#8221;</p><p>&#8220;Maybe I&#8217;m being too picky.&#8221;</p><p>That is how people talk themselves into future heartbreak.</p><p>The red flags you ignore in the beginning rarely disappear.</p><p>They usually become the reasons the relationship ends.</p><h2>Rule 6: Learn the Difference Between Being Wanted and Being Valued</h2><p>Many men will want you.</p><p>Far fewer will value you.</p><p>Being wanted is easy.</p><p>Being valued is different.</p><p>A man may desire your body and ignore your dreams.</p><p>Desire your company and ignore your boundaries.</p><p>Desire your attention and disappear when you need support.</p><p>Value shows up differently.</p><p>Value respects.</p><p>Value listens.</p><p>Value protects.</p><p>Value stays.</p><p>Do not confuse attention with investment.</p><h2>Rule 7: Stop Trying to Earn Love</h2><p>One of the saddest things I see is women trying to become lovable enough.</p><p>More accommodating.</p><p>More patient.</p><p>More understanding.</p><p>More forgiving.</p><p>More available.</p><p>More useful.</p><p>Love is not a university degree.</p><p>You do not earn it through performance.</p><p>The right relationship does not require you to audition indefinitely.</p><h2>Rule 8: Ask Hard Questions Early</h2><p>One of the advantages of being over 35 is that you no longer need to waste time pretending.</p><p>Ask questions.</p><p>What do you want?</p><p>Why did your last relationship end?</p><p>How do you handle conflict?</p><p>Do you want marriage?</p><p>Children?</p><p>Commitment?</p><p>Many people avoid these conversations because they fear appearing too serious.</p><p>The irony is that avoiding them usually creates bigger problems later.</p><p>Clarity saves time.</p><h2>Rule 9: Build a Life That Does Not Depend on a Relationship</h2><p>The happiest people I know are not the ones who found love.</p><p>They are the ones who built meaningful lives.</p><p>Some are married.</p><p>Some are single.</p><p>Some are dating.</p><p>Some are not.</p><p>But all of them have lives that extend beyond romance.</p><p>Friends.</p><p>Purpose.</p><p>Hobbies.</p><p>Faith.</p><p>Family.</p><p>Work.</p><p>Community.</p><p>A relationship should enhance your life.</p><p>It should not become your life.</p><h2>Rule 10: Choose Peace</h2><p>When I was younger, I thought love was supposed to feel like fireworks.</p><p>Now I suspect it feels more like coming home.</p><p>The older you get, the more valuable peace becomes.</p><p>Not boredom.</p><p>Not indifference.</p><p>Peace.</p><p>The kind that allows you to be yourself.</p><p>The kind that allows you to exhale.</p><p>The kind that makes your life larger instead of smaller.</p><p>The kind that helps you become more of who you are.</p><p>Many women spend years searching for excitement.</p><p>The wiser ones eventually start searching for peace.</p><p>And when they find it, they rarely let it go.</p><h2>A Final Thought</h2><p>A few years ago, I asked a woman what she had learned from divorce.</p><p>I expected her to say something profound about men.</p><p>Or marriage.</p><p>Or heartbreak.</p><p>Instead, she smiled and said:</p><p>&#8220;I learned that being chosen is not the same thing as being loved.&#8221;</p><p>Then she paused.</p><p>&#8220;And being alone is not the same thing as being lonely.&#8221;</p><p>I have never forgotten those words.</p><p>Many women over 35 carry invisible scars.</p><p>Some were left.</p><p>Some were betrayed.</p><p>Some buried the love of their lives.</p><p>Some spent years building relationships that never became what they hoped they would become.</p><p>Others spent so long taking care of everyone else that they forgot to take care of themselves.</p><p>If that is your story, let me tell you something.</p><p>You are not behind.</p><p>You are not damaged.</p><p>You are not too old.</p><p>And you are certainly not running out of time.</p><p>The goal is not to find someone.</p><p>The goal is to find someone worthy of what life has taught you.</p><p>Someone who appreciates the wisdom that came from your failures.</p><p>Someone who values the strength that emerged from your pain.</p><p>Someone who understands that love is not merely a feeling.</p><p>It is a responsibility.</p><p>A choice.</p><p>A commitment.</p><p>A daily act of care.</p><p>And if you never find that person?</p><p>Build a life so rich, meaningful, joyful, and peaceful that love becomes a beautiful addition rather than a desperate necessity.</p><p>Because the healthiest relationships are not built by two people trying to complete each other.</p><p>They are built by two people who have already learned how to stand on their own.</p><p>The truth is that dating after 35 is not harder because there are fewer good people.</p><p>It is harder because you finally understand the cost of choosing the wrong one.</p><p>And perhaps that is not a disadvantage at all.</p><p>Perhaps that is wisdom.</p><p>If this article resonated with you, share it with a woman who may need to read it.</p><p>And if you enjoyed it, consider subscribing and joining the conversation.</p><p>Until next time.</p><p><strong>Martins</strong></p><p>The Diary of a Playboy</p><p>P.S. If this piece made you think, smile, reflect, or see your own journey a little differently, you can always buy the author a coffee. It helps keep these conversations alive.</p><p><em>If you enjoyed this article, you may also like:</em></p><p><a href="iframe.php?url=https%3A%2F%2Fthediaryofaplayboy.substack.com%2Fp%2Fcan-cheating-save-a-marriage">Can Cheating Save a Marriage?</a></p><p><a href="iframe.php?url=https%3A%2F%2Fthediaryofaplayboy.substack.com%2Fp%2Fdont-be-with-people-who-dont-want">don't Be With People Who Don't Want You</a></p><p><a href="iframe.php?url=https%3A%2F%2Fthediaryofaplayboy.substack.com%2Fp%2Fhow-to-have-difficult-conversations">HOW TO HAVE DIFFICULT CONVERSATIONS IN A RELATIONSHIP</a></p><p><a href="iframe.php?url=https%3A%2F%2Fthediaryofaplayboy.substack.com%2Fp%2Fwhy-does-cheating-hit-men-so-hard">Why Does Cheating Hit Men So Hard?</a></p><div class="subscription-widget-wrap-editor" data-attrs="{&quot;url&quot;:&quot;https://thediaryofaplayboy.substack.com/subscribe?&quot;,&quot;text&quot;:&quot;Subscribe&quot;,&quot;language&quot;:&quot;en&quot;}" data-component-name="SubscribeWidgetToDOM"><div class="subscription-widget show-subscribe"><div class="preamble"><p class="cta-caption">The Diary of a Playboy is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.</p></div><form class="subscription-widget-subscribe"><input type="email" class="email-input" name="email" placeholder="Type your email&#8230;" tabindex="-1"><input type="submit" class="button primary" value="Subscribe"><div class="fake-input-wrapper"><div class="fake-input"></div><div class="fake-button"></div></div></form></div></div>]]></content:encoded></item><item><title><![CDATA[Can Cheating Save a Marriage?]]></title><description><![CDATA[Before you answer, consider the woman who spent years eating dinner alone.]]></description><link>https://thediaryofaplayboy.substack.com/p/can-cheating-save-a-marriage</link><guid isPermaLink="false">https://thediaryofaplayboy.substack.com/p/can-cheating-save-a-marriage</guid><dc:creator><![CDATA[Martins Itua]]></dc:creator><pubDate>Mon, 01 Jun 2026 15:18:59 GMT</pubDate><enclosure url="iframe.php?url=https%3A%2F%2Fsubstackcdn.com%2Fimage%2Ffetch%2F%24s_%21vO95%21%2Cf_auto%2Cq_auto%3Agood%2Cfl_progressive%3Asteep%2Fhttps%253A%252F%252Fsubstack-post-media.s3.amazonaws.com%252Fpublic%252Fimages%252F90d17a39-70de-43c1-bde5-315194900f2a_1024x1536.png" length="0" type="image/jpeg"/><content:encoded><![CDATA[<p>Every evening at exactly 7:00 p.m., she set the table for two.</p><p>Not because her husband was home.</p><div class="subscription-widget-wrap-editor" data-attrs="{&quot;url&quot;:&quot;https://thediaryofaplayboy.substack.com/subscribe?&quot;,&quot;text&quot;:&quot;Subscribe&quot;,&quot;language&quot;:&quot;en&quot;}" data-component-name="SubscribeWidgetToDOM"><div class="subscription-widget show-subscribe"><div class="preamble"><p class="cta-caption">The Diary of a Playboy is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.</p></div><form class="subscription-widget-subscribe"><input type="email" class="email-input" name="email" placeholder="Type your email&#8230;" tabindex="-1"><input type="submit" class="button primary" value="Subscribe"><div class="fake-input-wrapper"><div class="fake-input"></div><div class="fake-button"></div></div></form></div></div><p>But because he said he would be.</p><p>Again.</p><p>The food would get cold.</p><p>The candles would burn out.</p><p>The excuses would arrive hours later.</p><p>A meeting.</p><p>A client.</p><p>Traffic.</p><p>An emergency.</p><p>Sometimes nothing at all.</p><p>She learned not to ask too many questions because the answers usually hurt more than the silence.</p><p>She saw the photographs.</p><p>The hotel bookings.</p><p>The suspicious transactions.</p><p>The holidays he somehow never mentioned.</p><p>The women who appeared too frequently in stories that never quite made sense.</p><p>Yet she stayed.</p><p>Not because she was weak.</p><p>Not because she lacked options.</p><p>But because life is rarely as simple as people on the internet pretend.</p><p>There were children.</p><p>Memories.</p><p>A mortgage.</p><p>A shared history.</p><p>And somewhere beneath the disappointment, there was still love. Or at least the memory of it.</p><p>So she waited.</p><p>She waited for him to come home.</p><p>She waited for him to choose her.</p><p>She waited for him to become the man he used to be.</p><p>And like many people trapped in unhappy marriages, she slowly built her entire emotional life around someone who had stopped showing up for it.</p><p>Then one day something changed.</p><p>Not in him.</p><p>In her.</p><p>She stopped waiting.</p><p>The arguments stopped.</p><p>The pleading stopped.</p><p>The investigations stopped.</p><p>The tears stopped.</p><p>She started having lunch with friends.</p><p>She started travelling.</p><p>She rediscovered old hobbies.</p><p>She went dancing.</p><p>She laughed more.</p><p>She smiled more.</p><p>And eventually, she met other men.</p><p>Some became friends.</p><p>Some became companions.</p><p>Some became lovers.</p><p>For the first time in years, her happiness no longer depended on whether her husband came home.</p><p>And that is where this story becomes uncomfortable.</p><p>Because the happier she became, the more interested her husband became.</p><p>The woman who had spent years begging for attention was suddenly no longer asking for it.</p><p>The woman he had taken for granted was suddenly alive again.</p><p>Which raises a question many people are afraid to ask out loud:</p><p>What if the affair was not the thing that destroyed the marriage?</p><p>What if the marriage had been dying for years already?</p><p>And what if what people call cheating was, in some cases, a desperate attempt to survive the loneliness that came first?</p><p>Before you answer, stay with me.</p><p>Because this conversation is not really about cheating.</p><p>It is about loneliness.</p><p>It is about neglect.</p><p>It is about loyalty.</p><p>It is about self respect.</p><p>And it is about the uncomfortable difference between being married and actually having a marriage.</p><div class="captioned-image-container"><figure><a class="image-link image2 is-viewable-img" target="_blank" href="iframe.php?url=https%3A%2F%2Fsubstackcdn.com%2Fimage%2Ffetch%2F%24s_%21vO95%21%2Cf_auto%2Cq_auto%3Agood%2Cfl_progressive%3Asteep%2Fhttps%253A%252F%252Fsubstack-post-media.s3.amazonaws.com%252Fpublic%252Fimages%252F90d17a39-70de-43c1-bde5-315194900f2a_1024x1536.png" data-component-name="Image2ToDOM"><div class="image2-inset"><picture><source type="image/webp" srcset="https://substackcdn.com/image/fetch/$s_!vO95!,w_424,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F90d17a39-70de-43c1-bde5-315194900f2a_1024x1536.png 424w, https://substackcdn.com/image/fetch/$s_!vO95!,w_848,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F90d17a39-70de-43c1-bde5-315194900f2a_1024x1536.png 848w, https://substackcdn.com/image/fetch/$s_!vO95!,w_1272,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F90d17a39-70de-43c1-bde5-315194900f2a_1024x1536.png 1272w, https://substackcdn.com/image/fetch/$s_!vO95!,w_1456,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F90d17a39-70de-43c1-bde5-315194900f2a_1024x1536.png 1456w" sizes="auto, 100vw"><img src="iframe.php?url=https%3A%2F%2Fsubstackcdn.com%2Fimage%2Ffetch%2F%24s_%21vO95%21%2Cw_1456%2Cc_limit%2Cf_auto%2Cq_auto%3Agood%2Cfl_progressive%3Asteep%2Fhttps%253A%252F%252Fsubstack-post-media.s3.amazonaws.com%252Fpublic%252Fimages%252F90d17a39-70de-43c1-bde5-315194900f2a_1024x1536.png" width="1024" height="1536" 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srcset="https://substackcdn.com/image/fetch/$s_!vO95!,w_424,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F90d17a39-70de-43c1-bde5-315194900f2a_1024x1536.png 424w, https://substackcdn.com/image/fetch/$s_!vO95!,w_848,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F90d17a39-70de-43c1-bde5-315194900f2a_1024x1536.png 848w, https://substackcdn.com/image/fetch/$s_!vO95!,w_1272,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F90d17a39-70de-43c1-bde5-315194900f2a_1024x1536.png 1272w, https://substackcdn.com/image/fetch/$s_!vO95!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F90d17a39-70de-43c1-bde5-315194900f2a_1024x1536.png 1456w" sizes="auto, 100vw" loading="lazy"></picture><div class="image-link-expand"><div class="pencraft pc-display-flex pc-gap-8 pc-reset"><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container restack-image buttonBase-GK1x3M"><svg aria-hidden="true" width="20" height="20" viewBox="0 0 20 20" fill="none" stroke-width="1.5" stroke="var(--color-fg-primary)" stroke-linecap="round" stroke-linejoin="round" xmlns="http://www.w3.org/2000/svg" class="icon-noB79L"><g><path d="M2.53001 7.81595C3.49179 4.73911 6.43281 2.5 9.91173 2.5C13.1684 2.5 15.9537 4.46214 17.0852 7.23684L17.6179 8.67647M17.6179 8.67647L18.5002 4.26471M17.6179 8.67647L13.6473 6.91176M17.4995 12.1841C16.5378 15.2609 13.5967 17.5 10.1178 17.5C6.86118 17.5 4.07589 15.5379 2.94432 12.7632L2.41165 11.3235M2.41165 11.3235L1.5293 15.7353M2.41165 11.3235L6.38224 13.0882"></path></g></svg></button><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container view-image buttonBase-GK1x3M"><svg xmlns="http://www.w3.org/2000/svg" width="20" height="20" viewBox="0 0 24 24" fill="none" stroke="currentColor" stroke-width="2" stroke-linecap="round" stroke-linejoin="round" class="lucide lucide-maximize2 lucide-maximize-2 icon-noB79L"><polyline points="15 3 21 3 21 9"></polyline><polyline points="9 21 3 21 3 15"></polyline><line x1="21" x2="14" y1="3" y2="10"></line><line x1="3" x2="10" y1="21" y2="14"></line></svg></button></div></div></div></a></figure></div><h2>The Lie We Tell Ourselves About Cheating</h2><p>Most people think they know exactly when a marriage ends.</p><p>It ends when someone cheats.</p><p>Case closed.</p><p>But life is rarely that simple.</p><p>A husband spends five years ignoring his wife emotionally.</p><p>A wife spends ten years humiliating her husband publicly.</p><p>A husband repeatedly chooses work, friends, alcohol, or other women over his family.</p><p>A wife weaponizes affection and intimacy until it becomes a bargaining tool rather than an expression of love.</p><p>Nobody calls these affairs.</p><p>Yet every one of them involves giving something that belongs inside the marriage to something outside it.</p><p>Attention.</p><p>Affection.</p><p>Energy.</p><p>Desire.</p><p>Respect.</p><p>Presence.</p><p>The truth is that many marriages die long before anyone enters another person&#8217;s bedroom.</p><p>They die in silence.</p><p>They die in neglect.</p><p>They die in loneliness.</p><p>They die when one partner repeatedly says, &#8220;I need you,&#8221; and the other partner stops listening.</p><p>This is why the conversation around infidelity is often incomplete.</p><p>We focus on the final act.</p><p>We rarely examine the years that preceded it.</p><p>Imagine a woman who spends fifteen years feeling unwanted.</p><p>Her husband provides financially.</p><p>He is physically present.</p><p>He is technically faithful.</p><p>But he does not see her.</p><p>He does not notice when she cries.</p><p>He does not ask how she is doing.</p><p>He does not remember what matters to her.</p><p>He has not made her feel desired in years.</p><p>Now ask yourself a difficult question.</p><p>Is she in a healthy marriage?</p><p>Most people know the answer.</p><p>Yet because no sex occurred outside the marriage, society often treats the relationship as intact.</p><p>This is one of the greatest misconceptions about commitment.</p><p>Sexual fidelity is important.</p><p>But it is not the only form of fidelity.</p><p>You can be sexually faithful while being emotionally absent.</p><p>You can sleep in the same bed every night and still abandon your spouse.</p><p>You can remain legally married while becoming relationally unavailable.</p><p>Many people are shocked by affairs because they believe betrayal begins with sex.</p><p>In reality, sex is often the last chapter of a much longer story.</p><p>Sometimes the betrayal began years earlier.</p><p>The moment one partner stopped showing up.</p><p>The moment one partner stopped caring.</p><p>The moment one partner decided the marriage could survive indefinitely on crumbs.</p><p>None of this justifies infidelity.</p><p>But it does force us to ask harder questions.</p><p>Questions that are less comfortable than simply identifying a villain.</p><p>Questions like:</p><p>How much loneliness can a human being endure?</p><p>How many promises can be broken before a person breaks too?</p><p>How long should someone remain loyal to a marriage that has stopped being loyal to them?</p><p>Those questions have no easy answers.</p><p>And that is precisely why this conversation matters.</p><h2>So, Can Cheating Save a Marriage?</h2><p>The honest answer is that sometimes it does.</p><p>And sometimes it destroys it completely.</p><p>Some marriages survive affairs and emerge stronger because the affair exposed problems both partners had spent years avoiding.</p><p>Others collapse because the trust never returns.</p><p>Some people leave.</p><p>Some people stay.</p><p>Some forgive.</p><p>Some cannot.</p><p>Life is messy like that.</p><p>What I know is this:</p><p>Most people spend their energy arguing about whether cheating is right or wrong.</p><p>Far fewer spend time asking why so many people become vulnerable to it in the first place.</p><p>A starving person is not thinking about nutrition.</p><p>A drowning person is not thinking about swimming technique.</p><p>And a deeply lonely person is often not thinking as clearly as people imagine.</p><p>That does not excuse bad decisions.</p><p>But it helps explain them.</p><p>The real lesson is not that people should cheat.</p><p>The real lesson is that no marriage can survive indefinitely on duty alone.</p><p>Human beings need more than legal contracts.</p><p>They need attention.</p><p>Affection.</p><p>Respect.</p><p>Desire.</p><p>Friendship.</p><p>Presence.</p><p>And when those things disappear, something else eventually takes their place.</p><p>Sometimes it is resentment.</p><p>Sometimes it is depression.</p><p>Sometimes it is alcohol.</p><p>Sometimes it is work.</p><p>And sometimes it is another person.</p><p>That is why the most important question in this entire discussion is not:</p><p>&#8220;Would you forgive cheating?&#8221;</p><p>The more uncomfortable question is:</p><p>&#8220;What have you allowed to die in your marriage while focusing on everything else?&#8221;</p><p>Because long before people leave physically, they usually leave emotionally.</p><p>And by the time an affair appears, the story may have started years earlier.</p><p>So I will leave you with one final question.</p><p>If your spouse became emotionally alive, happy, confident, desirable, and independent tomorrow, would it strengthen your marriage?</p><p>Or would it expose how dependent the marriage has become on one person doing all the waiting?</p><p>Think carefully before you answer.</p><p>Because the answer may tell you more about your relationship than any affair ever could.</p><p><em>If this piece made you think, challenged your assumptions, or reminded you of a conversation someone needs to have, consider sharing it.</em></p><p>And if you enjoy thoughtful, uncomfortable, and deeply human conversations about love, relationships, self worth, heartbreak, healing, and what it means to be human, subscribe and join the community.</p><p>And if you would like to support the work and help keep these conversations going, you can always buy the author a coffee.</p><p>Until next time.</p><p>Martins<br>The Diary of a Playboy</p><div class="subscription-widget-wrap-editor" data-attrs="{&quot;url&quot;:&quot;https://thediaryofaplayboy.substack.com/subscribe?&quot;,&quot;text&quot;:&quot;Subscribe&quot;,&quot;language&quot;:&quot;en&quot;}" data-component-name="SubscribeWidgetToDOM"><div class="subscription-widget show-subscribe"><div class="preamble"><p class="cta-caption">The Diary of a Playboy is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.</p></div><form class="subscription-widget-subscribe"><input type="email" class="email-input" name="email" placeholder="Type your email&#8230;" tabindex="-1"><input type="submit" class="button primary" value="Subscribe"><div class="fake-input-wrapper"><div class="fake-input"></div><div class="fake-button"></div></div></form></div></div>]]></content:encoded></item><item><title><![CDATA[THE CRUELEST PEOPLE I KNOW CRY THE MOST]]></title><description><![CDATA[I once knew someone who cried at everything.]]></description><link>https://thediaryofaplayboy.substack.com/p/the-cruelest-people-i-know-cry-the</link><guid isPermaLink="false">https://thediaryofaplayboy.substack.com/p/the-cruelest-people-i-know-cry-the</guid><dc:creator><![CDATA[Martins Itua]]></dc:creator><pubDate>Tue, 26 May 2026 07:43:09 GMT</pubDate><enclosure url="iframe.php?url=https%3A%2F%2Fsubstackcdn.com%2Fimage%2Ffetch%2F%24s_%21dAdx%21%2Cf_auto%2Cq_auto%3Agood%2Cfl_progressive%3Asteep%2Fhttps%253A%252F%252Fsubstack-post-media.s3.amazonaws.com%252Fpublic%252Fimages%252F656da724-6a45-48b9-9718-37fd53300797_1023x1537.png" length="0" type="image/jpeg"/><content:encoded><![CDATA[<div class="captioned-image-container"><figure><a class="image-link image2 is-viewable-img" target="_blank" href="iframe.php?url=https%3A%2F%2Fsubstackcdn.com%2Fimage%2Ffetch%2F%24s_%21dAdx%21%2Cf_auto%2Cq_auto%3Agood%2Cfl_progressive%3Asteep%2Fhttps%253A%252F%252Fsubstack-post-media.s3.amazonaws.com%252Fpublic%252Fimages%252F656da724-6a45-48b9-9718-37fd53300797_1023x1537.png" data-component-name="Image2ToDOM"><div class="image2-inset"><picture><source type="image/webp" srcset="https://substackcdn.com/image/fetch/$s_!dAdx!,w_424,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F656da724-6a45-48b9-9718-37fd53300797_1023x1537.png 424w, https://substackcdn.com/image/fetch/$s_!dAdx!,w_848,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F656da724-6a45-48b9-9718-37fd53300797_1023x1537.png 848w, https://substackcdn.com/image/fetch/$s_!dAdx!,w_1272,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F656da724-6a45-48b9-9718-37fd53300797_1023x1537.png 1272w, https://substackcdn.com/image/fetch/$s_!dAdx!,w_1456,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F656da724-6a45-48b9-9718-37fd53300797_1023x1537.png 1456w" sizes="100vw"><img src="iframe.php?url=https%3A%2F%2Fsubstackcdn.com%2Fimage%2Ffetch%2F%24s_%21dAdx%21%2Cw_1456%2Cc_limit%2Cf_auto%2Cq_auto%3Agood%2Cfl_progressive%3Asteep%2Fhttps%253A%252F%252Fsubstack-post-media.s3.amazonaws.com%252Fpublic%252Fimages%252F656da724-6a45-48b9-9718-37fd53300797_1023x1537.png" width="1023" height="1537" data-attrs="{&quot;src&quot;:&quot;https://substack-post-media.s3.amazonaws.com/public/images/656da724-6a45-48b9-9718-37fd53300797_1023x1537.png&quot;,&quot;srcNoWatermark&quot;:null,&quot;fullscreen&quot;:null,&quot;imageSize&quot;:null,&quot;height&quot;:1537,&quot;width&quot;:1023,&quot;resizeWidth&quot;:null,&quot;bytes&quot;:1935213,&quot;alt&quot;:null,&quot;title&quot;:null,&quot;type&quot;:&quot;image/png&quot;,&quot;href&quot;:null,&quot;belowTheFold&quot;:false,&quot;topImage&quot;:true,&quot;internalRedirect&quot;:&quot;https://thediaryofaplayboy.substack.com/i/199294274?img=https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F656da724-6a45-48b9-9718-37fd53300797_1023x1537.png&quot;,&quot;isProcessing&quot;:false,&quot;align&quot;:null,&quot;offset&quot;:false}" class="sizing-normal" alt="" srcset="https://substackcdn.com/image/fetch/$s_!dAdx!,w_424,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F656da724-6a45-48b9-9718-37fd53300797_1023x1537.png 424w, https://substackcdn.com/image/fetch/$s_!dAdx!,w_848,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F656da724-6a45-48b9-9718-37fd53300797_1023x1537.png 848w, https://substackcdn.com/image/fetch/$s_!dAdx!,w_1272,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F656da724-6a45-48b9-9718-37fd53300797_1023x1537.png 1272w, https://substackcdn.com/image/fetch/$s_!dAdx!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F656da724-6a45-48b9-9718-37fd53300797_1023x1537.png 1456w" sizes="100vw" fetchpriority="high"></picture><div class="image-link-expand"><div class="pencraft pc-display-flex pc-gap-8 pc-reset"><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container restack-image buttonBase-GK1x3M"><svg aria-hidden="true" width="20" height="20" viewBox="0 0 20 20" fill="none" stroke-width="1.5" stroke="var(--color-fg-primary)" stroke-linecap="round" stroke-linejoin="round" xmlns="http://www.w3.org/2000/svg" class="icon-noB79L"><g><path d="M2.53001 7.81595C3.49179 4.73911 6.43281 2.5 9.91173 2.5C13.1684 2.5 15.9537 4.46214 17.0852 7.23684L17.6179 8.67647M17.6179 8.67647L18.5002 4.26471M17.6179 8.67647L13.6473 6.91176M17.4995 12.1841C16.5378 15.2609 13.5967 17.5 10.1178 17.5C6.86118 17.5 4.07589 15.5379 2.94432 12.7632L2.41165 11.3235M2.41165 11.3235L1.5293 15.7353M2.41165 11.3235L6.38224 13.0882"></path></g></svg></button><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container view-image buttonBase-GK1x3M"><svg xmlns="http://www.w3.org/2000/svg" width="20" height="20" viewBox="0 0 24 24" fill="none" stroke="currentColor" stroke-width="2" stroke-linecap="round" stroke-linejoin="round" class="lucide lucide-maximize2 lucide-maximize-2 icon-noB79L"><polyline points="15 3 21 3 21 9"></polyline><polyline points="9 21 3 21 3 15"></polyline><line x1="21" x2="14" y1="3" y2="10"></line><line x1="3" x2="10" y1="21" y2="14"></line></svg></button></div></div></div></a></figure></div><p>I once knew someone who cried at everything.</p><p>The news.<br>Wedding videos.<br>Children playing in the street.</p><div class="subscription-widget-wrap-editor" data-attrs="{&quot;url&quot;:&quot;https://thediaryofaplayboy.substack.com/subscribe?&quot;,&quot;text&quot;:&quot;Subscribe&quot;,&quot;language&quot;:&quot;en&quot;}" data-component-name="SubscribeWidgetToDOM"><div class="subscription-widget show-subscribe"><div class="preamble"><p class="cta-caption">The Diary of a Playboy is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.</p></div><form class="subscription-widget-subscribe"><input type="email" class="email-input" name="email" placeholder="Type your email&#8230;" tabindex="-1"><input type="submit" class="button primary" value="Subscribe"><div class="fake-input-wrapper"><div class="fake-input"></div><div class="fake-button"></div></div></form></div></div><p>People called her compassionate. A rare soul.</p><p>She was also the most quietly devastating person I have ever been close to.</p><p>Not loudly. She never raised her voice. But somehow, every difficult conversation ended with me apologizing for things I did not do. Every moment of vulnerability I offered somehow became about her feelings instead. Every time I said something feels off between us, she cried. And I would spend the next hour comforting her for the pain she caused me.</p><p>It took me years to understand what I was actually seeing.</p><p>Because feeling deeply is not the same thing as empathy.</p><p>And some of the most emotionally unavailable people you will ever meet are the ones who speak most beautifully about emotions.</p><p>That realization unsettled me deeply because for a long time, I thought empathy was about sensitivity. I thought the people who cried easily were naturally the safest people to love.</p><p>I was wrong.</p><p>Empathy is not measured by how emotional you are.</p><p>It is measured by how safe people feel bringing their emotions to you.</p><p>And the difference between those two things quietly destroys relationships every single day.</p><p>Most people do not realize how emotionally alone they feel until they try to explain their pain to someone who keeps turning the conversation back toward themselves.</p><p>You tell someone you feel lonely in the relationship.</p><p>Instead of asking why, they immediately begin listing everything they have done for you.</p><p>You tell someone you are overwhelmed.</p><p>Before you finish speaking, they start giving advice.</p><p>You try to explain why something hurt you.</p><p>They become defensive, emotional, withdrawn, or suddenly become the real victim in the conversation.</p><p>So now instead of processing your pain, you are managing theirs.</p><p>That exhaustion changes people.</p><p>It teaches people to stop speaking honestly.</p><p>It teaches people to emotionally shrink themselves to avoid triggering reactions.</p><p>It teaches people that vulnerability is unsafe.</p><p>And the frightening thing is that many emotionally unavailable people genuinely believe they are empathetic simply because they feel things intensely.</p><p>But emotion alone is not empathy.</p><p>Sometimes emotion is just self absorption with tears.</p><p>Real empathy requires presence.</p><p>Attention.</p><p>Curiosity.</p><p>The willingness to leave your own emotional experience long enough to fully enter someone else&#8217;s.</p><p>That is much harder than crying.</p><p>I learned this painfully in my own life.</p><p>There were moments people I loved did not need my solutions. They needed my attention.</p><p>But like many people, I confused fixing with caring.</p><p>Someone would tell me about a painful experience and before they even finished speaking, I was already trying to solve it. Reframing it. Offering perspective. Looking for the lesson. Looking for the positive side.</p><p>I thought I was helping.</p><p>What I was actually doing was trying to escape discomfort as quickly as possible.</p><p>Because sitting with another person&#8217;s pain without trying to control it requires emotional maturity many people simply never learned.</p><p>Including me.</p><p>And honestly, once you begin seeing this clearly, you notice it everywhere.</p><p>You see it in marriages where couples have not truly felt emotionally heard in years even though they talk every day.</p><p>You see it in parents who provide financially for their children but emotionally disappear whenever feelings become uncomfortable.</p><p>You see it in friendships where one person is always emotionally carrying the relationship while the other simply performs concern beautifully.</p><p>You see it in workplaces where managers ask &#8220;How are you?&#8221; but clearly do not want the real answer.</p><p>You see it online constantly.</p><p>People posting paragraphs about healing, softness, vulnerability, emotional intelligence, and self awareness while quietly leaving destruction behind them in private relationships.</p><p>And the truth is uncomfortable:</p><p>Some people use emotional expression the same way others use charm.</p><p>As performance.</p><p>As identity.</p><p>As social currency.</p><p>Not as connection.</p><p>That does not necessarily make them evil.</p><p>In fact, many of them are deeply wounded people.</p><p>People who learned very early in life that emotions were the only way to receive attention, safety, validation, or love.</p><p>People who were never taught how to stay emotionally present inside difficult conversations.</p><p>People who learned how to express feelings without ever learning how to hold someone else&#8217;s.</p><p>And that distinction changes everything.</p><p>Because there is a difference between someone who feels deeply and someone who can emotionally hold another human being safely.</p><p>One is emotional intensity.</p><p>The other is emotional availability.</p><p>They are not the same thing.</p><p>I think many people first learn emotional survival before they ever learn emotional connection.</p><p>A child cries and gets mocked for being dramatic.</p><p>A boy learns vulnerability makes him weak.</p><p>A girl learns her emotions only matter when they are pleasant for other people.</p><p>Someone grows up in a house where conflict becomes silence for days.</p><p>Someone else grows up around parents who never apologize, never explain, never repair emotional damage.</p><p>Children absorb these things quietly.</p><p>Then they become adults who desperately want intimacy while panicking the moment intimacy becomes emotionally real.</p><p>So they withdraw.</p><p>Deflect.</p><p>Over explain.</p><p>Fix.</p><p>Manipulate.</p><p>Disappear.</p><p>Cry.</p><p>Anything except remain emotionally present.</p><p>I realized this fully during my final conversation with Adaeze.</p><p>After years of confusion and emotional distance, I asked her something I had never asked before.</p><p>&#8220;Did anyone ever truly see you? Not your tears. Not your sensitivity. Just you.&#8221;</p><p>She was quiet for a very long time.</p><p>Then she said softly:</p><p>&#8220;I do not think I ever let anyone close enough to try.&#8221;</p><p>That answer stayed with me for years.</p><p>Because suddenly, everything made sense.</p><p>She was not emotionally withholding because she felt nothing.</p><p>She was emotionally unreachable because somewhere in life, vulnerability stopped feeling safe.</p><p>So instead of practicing connection, she practiced emotional performance.</p><p>Still, understanding someone&#8217;s wounds does not erase the damage they cause.</p><p>And this is important.</p><p>Because too many people stay trapped in painful relationships trying to psychoanalyze someone into becoming emotionally available.</p><p>Understanding pain and tolerating emotional harm are not the same thing.</p><p>Some people are not ready to love beyond their own survival patterns yet.</p><p>And no amount of patience can force emotional maturity onto someone who refuses to confront themselves honestly.</p><p>That realization hurts.</p><p>Especially when the person is not cruel.</p><p>Just unavailable.</p><p>Those are often the hardest people to leave.</p><p>Because there is enough goodness to keep you hoping.</p><p>Enough tenderness to confuse you.</p><p>Enough emotion to make you believe connection is happening.</p><p>While quietly, slowly, you continue feeling unseen.</p><p>And if we are honest, many of us have also been that person for others at different points in our lives.</p><p>That is the harder part of this conversation.</p><p>Not asking:<br>&#8220;Who failed to emotionally see me?&#8221;</p><p>But asking:<br>&#8220;Who feels emotionally unseen around me?&#8221;</p><p>Who stopped bringing things to you because your reactions never felt safe enough?</p><p>Who needed listening and received advice instead?</p><p>Who needed presence and received performance?</p><p>Who quietly gave up trying to emotionally reach you?</p><p>Those questions require a different kind of courage.</p><p>But that courage is where real empathy begins.</p><p>Not in tears.</p><p>Not in sensitivity.</p><p>Not in saying the right things.</p><p>But in developing the ability to remain emotionally present long enough for another human being to feel fully real beside you.</p><p>That is rare.</p><p>Rarer than people think.</p><p>And honestly, I believe it may be one of the purest forms of love left.</p><p><em>If this piece stayed with you, share it with someone who may need it too. And if these are the kinds of conversations you want more of, stay awhile.</em></p><p>And if this piece earned it, maybe buy the author coffee before you go.</p><div class="subscription-widget-wrap-editor" data-attrs="{&quot;url&quot;:&quot;https://thediaryofaplayboy.substack.com/subscribe?&quot;,&quot;text&quot;:&quot;Subscribe&quot;,&quot;language&quot;:&quot;en&quot;}" data-component-name="SubscribeWidgetToDOM"><div class="subscription-widget show-subscribe"><div class="preamble"><p class="cta-caption">The Diary of a Playboy is a reader-supported publication. 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