Dear Black Gay Men Podcast
Dear Black Gay Men Podcast

Dear Black Gay Men Podcast

Jai The Gentleman

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Episodes

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Dear Black Gay Men Weekly is your weekly dopeness reminder and your favorite content creator’s favorite content.

dearblackgaymen.substack.com

Recent Episodes

🎬 Diddy, Documentaries, and Dollars: The Black Gay Take on ‘Sean Combs: The Reckoning’
DEC 9, 2025
🎬 Diddy, Documentaries, and Dollars: The Black Gay Take on ‘Sean Combs: The Reckoning’
<p>On this episode of the <strong>Dear Black Gay Men Podcast</strong> where we dive into the explosive documentary, <em>Sean Combs: The Reckoning</em>. Join <strong>Jai the Gentleman</strong> as he unpacks the fall of a Black culture icon and asks the tough questions about integrity, business, and big visions.</p><p>🚨 The Reckoning: What the Doc Alleges</p><p>The four-part Netflix series, executive produced by Curtis “50 Cent” Jackson and directed by Alexandria Stapleton, chronicles Diddy’s career from his start at Uptown Records through his recent legal troubles. Jai and the chat discuss the shocking allegations that Diddy was involved in:</p><p>* The murders of Tupac and Biggie.</p><p>* The <strong>death and tragedy</strong> that allegedly fueled his superstardom, including the nine lives lost at a celebrity basketball game he promoted.</p><p>* The alleged sexual violation of countless women and men.</p><p>💡 Big Visions vs. Bad Business</p><p>The conversation shifts from celebrity scandals to lessons for the community. Jai emphasizes the importance of <strong>integrity in Black gay business</strong>. Citing Diddy and others, he stresses that success must be built on honesty:</p><p>* <strong>Pay people well and on time.</strong> Black businesses often struggle with poor practices, leading to talent leaving for better opportunities.</p><p>* <strong>Maintain integrity and avoid blurred lines.</strong> Jai points out that issues of abuse of power can play out even in Black queer spaces.</p><p>* <strong>Have a Big Vision!</strong> While Diddy and others were “fucked up how they pursued that vision,” they fundamentally aimed for something monumental, a mindset Jai encourages the Black gay community to adopt in business and in love.</p><p>💬 Hookup Culture Hot Take</p><p>Jai also sparks a viral debate on gay hookup protocol, asking: Should you log onto the apps <em>after</em> you’re fully prepped, or risk a wasted shower and a missed connection?</p><p><strong>Tune in</strong> for the full discussion on this monumental doc and what it teaches us about our culture, business practices, and relationships.</p><p><p>Dear Black Gay Men’s Substack is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.</p></p><p></p> <br/><br/>This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit <a href="https://dearblackgaymen.substack.com/subscribe?utm_medium=podcast&#38;utm_campaign=CTA_2">dearblackgaymen.substack.com/subscribe</a>
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65 MIN
Reacting to RACEPLAY & White People’s Trauma Olympics feat. Nico’s Aesthetics
DEC 3, 2025
Reacting to RACEPLAY & White People’s Trauma Olympics feat. Nico’s Aesthetics
<p>Jai the Gentleman dives deep into some challenging and necessary conversations, navigating the complexities of race, sexuality, and community with his trademark blend of honesty and fire. The episode, titled “White People S**t,” centers on the realities faced by Black gay men today.</p><p>The Comfort Conundrum</p><p>The show kicks off with a provocative question: Would you rather be the lone gay person in an <strong>all-Black hetero space</strong> (like a family Thanksgiving) or the lone Black face in an <strong>all-queer white space</strong>? The chat was split, leading to a crucial discussion about navigating predominantly straight Black environments versus predominately white queer ones. Jai shares how getting older gave him the confidence to stop shrinking and moving through life as a “one life gay” man—the same everywhere he goes.</p><p>Conversion and Kink: The Race Play Debacle</p><p>Jai then shifts to reacting to a reel featuring a white gay man who claims, “Jesus is all the man I need” and “No, I will not date a boy,” framing it as a modernized version of conversion ideology. He connects this to the problematic idea that Black people have historically been told they are “not good enough” unless they change.</p><p>The main story tackles the shocking case of “Big C,” a creator who built an OnlyFans empire on degrading Black and brown people through <strong>race play</strong> and racial slurs. Jai critiques insecure “doms” who confuse providing things with earning the right to lead, a flaw that leads to abuses of power, both in sexual scenes and real life.</p><p>Catch the full episode for more on these essential discussions, World AIDS Day observations, and a fun list of things the gays do that straights “just can’t handle”.</p><p><p>Dear Black Gay Men’s Substack is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.</p></p> <br/><br/>This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit <a href="https://dearblackgaymen.substack.com/subscribe?utm_medium=podcast&#38;utm_campaign=CTA_2">dearblackgaymen.substack.com/subscribe</a>
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78 MIN
Is the Dating Pool Trash, or Are We the Drama? 🤔
NOV 25, 2025
Is the Dating Pool Trash, or Are We the Drama? 🤔
<p>The latest episode of the <strong>Dear Black Gay Men Podcast</strong> tackles a question burning up the timelines: Is the dating pool really trash, or are we, the daters, the drama? Host <strong>Jai the Gentleman</strong> dives deep into this topic, reacting to the recent vlog, “32 and Dating is Trash,” by vlogger <a target="_blank" href="https://www.youtube.com/@deardondre"><strong>DearDondre</strong></a><a target="_blank" href="https://www.youtube.com/@deardondre">.</a></p><p>Jai and the chat audience explored the complexities of finding love and happiness, especially as Black gay men. Dondre, whom Jai affirms as attractive and having the best of intentions, often struggles to navigate the dating scene, even in a city like Houston, which Jai calls “the Atlanta of the other side of the South”. Dondre’s story, including paying for a man to fly out to see him and his complicated on-again, off-again relationship with an ex, sparked a lively conversation.</p><p>The community weighed in on the “three-strikes rule” for reaching out to someone you’re interested in, before calling it quits. Jai shared his own dating history, noting that sometimes the heart’s desire to be loved can “trump logic every single time”.</p><p>Ultimately, Jai concluded that while every “pool has piss in it” (meaning the dating pool does have problems ), if you acknowledge you’re standing in the “pissy part” and don’t move, then <strong>you are the problem</strong>. The path to healthier dating involves confronting your own unhealed trauma.</p><p>The underlying constant? <strong>We all just want to be loved</strong>.</p><p><p>Dear Black Gay Men’s Substack is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.</p></p> <br/><br/>This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit <a href="https://dearblackgaymen.substack.com/subscribe?utm_medium=podcast&#38;utm_campaign=CTA_2">dearblackgaymen.substack.com/subscribe</a>
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78 MIN
🎙️ Jess Hilarious Drama & Queer Culture’s Power: A Must-Hear Discussion
NOV 19, 2025
🎙️ Jess Hilarious Drama & Queer Culture’s Power: A Must-Hear Discussion
<p>The drama surrounding <a target="_blank" href="https://www.youtube.com/live/YC-qPfyeg9A?si=Qme8nhdzBXZbmrYb">Jess Hilarious’s controversial comments</a> about who can have babies and her subsequent firing from the <em>Ms. Pat Settles It</em> show is the main event on the latest episode of the <strong>Dear Black Gay Men Podcast</strong>. Host Jai the Gentleman dives deep into the fallout, offering an unfiltered look at why Jess’s actions continue to generate massive backlash within the queer community.</p><p>🛑 Why Jess Hilarious Can’t “Shut The F**k Up”</p><p>Jess Hilarious first sparked controversy with her “who’s looking out for black women?” debacle , and then doubled down with the scientifically inaccurate “only women can have babies” message on <em>The Breakfast Club</em>. This led to her getting fired from <em>The Ms. Pat Show</em>, a conversation that was later discussed by <a target="_blank" href="https://youtu.be/eN9haoM2q40?si=SivBdR1b022FR4I2">Ms. Pat and the show’s queer creator, Jordan E. Cooper, on The Breakfast Club</a>.</p><p>Jai argues that Jess keeps putting her “foot in her mouth” because controversy is her “whole shtick,” even suggesting it’s the reason she keeps her job at <em>The Breakfast Club.</em></p><p>🏳️‍🌈 The Real Power in the Room</p><p>A central theme of the episode is the immense, often unseen, power of <strong>Black queer people</strong> in the entertainment industry. Jai emphasizes a critical truth: “The gays run s**t”.</p><p>* If you offend all queer people with “dumb s**t,” you will get “booted”.</p><p>* There’s always a queer person in charge, be it the producer, writer, publicist, or executive producer.</p><p>* Jordan E. Cooper, the queer creator of <em>The Ms. Pat Show</em> and <em>Ms. Pat Settles It</em>, is a perfect example of this influence.</p><p>Jai’s message is clear: You “never win when you’re on the wrong side of queer culture”. The vast majority of <strong>Black queer culture</strong> is “aligned against Jess Hilarious” for her repeated offenses.</p> <br/><br/>This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit <a href="https://dearblackgaymen.substack.com/subscribe?utm_medium=podcast&#38;utm_campaign=CTA_2">dearblackgaymen.substack.com/subscribe</a>
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74 MIN
Lies, Love, and the “Trash” in Queer Culture
NOV 18, 2025
Lies, Love, and the “Trash” in Queer Culture
<p>Jai the Gentleman, dive into some seriously taboo topics: the little lies we tell ourselves, the journey to happiness, and, of course, dating horror storie.</p><p>This episode, we’re reacting to a harsh critique of gay culture that claims the Black gay community has turned “liberation into a members-only club”. The critique highlights exclusion based on masculinity, fitness, skin tone, and designer labels.</p><p><strong>Are We Really “Trash”?</strong></p><p>I challenge the idea that our culture is “trash.” While acknowledging that fatphobia, femmephobia, transphobia, and homophobia are real and exist even among queer people , I assert that if all you see is trash, you’re choosing to stay in the “trash part of the pool”.</p><p>As Black gay men, we have the freedom to pick and choose the rules by which we govern ourselves. We are elite , we are culture, we are art, and we are magic. If we focus on the greatness, we will receive it back. You can always move to the “metaphorical suburbs of gay culture”.</p><p><strong>Dating, Intentions, and the Atlanta Check-In</strong></p><p>We also break down a dating segment from <a target="_blank" href="https://youtu.be/ywuVhqTzNUY?si=TCz2-9x9Mu7-e7lT">Hopeless Romantic Society</a>, which features what I call the “most Atlanta date” ever —complete with questions about credit score, homeownership, and health insurance tier.</p><p>I discuss the importance of checking a man’s <strong>intention</strong> early in the relationship. Life speaks to you first in whispers, and we need to listen to those subtle signs, like a low integrity of word, instead of just waiting for huge red flags.</p><p>Ultimately, the gworls just want to be loved, but love is hard when you’re carrying unresolved issues. When you find a Black man to love you, and your puzzle pieces fit, you can’t beat that.</p><p><p>Dear Black Gay Men’s Substack is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.</p></p> <br/><br/>This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit <a href="https://dearblackgaymen.substack.com/subscribe?utm_medium=podcast&#38;utm_campaign=CTA_2">dearblackgaymen.substack.com/subscribe</a>
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75 MIN