Podcast
Dear Black Gay Men Podcast
Hosted by Jai The Gentleman · EN
Dear Black Gay Men Weekly is your weekly dopeness reminder and your favorite content creator’s favorite content.
dearblackgaymen.substack.com
dearblackgaymen.substack.com
29episodes
Episodes
Newest firstAll episodes
I Obsessed Over Being a Better Top (here's what I learned)
Sep 2501:23:18Tap to summarizeI talked 20 bottoms to bust myths tops have about good sex. Twenty conversations narrowed down to just 4 things that bottoms say tops can do to have immediately better sexWhether you’re dating someone new, in a long term relationship already, or just hooking up while you’re single, sex is an inevitable part of your life. We all want it and we all want ours to be the best.My whole job on this channel is to help Black gay men remember how dope it is to be us and to love us. Sometimes that interaction purely sexualSo if I can help tops give a performance that’s worth a bottom changing a diet and douching their life away, that’s a sacrifice I’m willing to make.Because the goal isn’t to just know WHAT bottoms say makes sex good, but to understand WHY THESE THINGS MAKE SEX GOOD.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.00:00:00 | Introduction: What Makes S*x Good?00:01:28 | Myth #1: Does Dick Size Really Matter?00:14:47 | Three Questions for Better S*x00:19:42 | Myth #2: Shorter S*x is Better00:30:13 | Top vs. Total Top: A Cultural Shift00:40:23 | Myth #3: The Power of Praise Kinks00:56:06 | Myth #4: Connection is Key (Even for Hookups)01:08:29 | Get to Know J.A.Y. & The Studio01:11:44 | Final Thoughts & The P*rn Debate01:21:53 | ConclusionThe host recaps the four key findings from his interviews with bottoms:* Husband dick is the perfect size* Multiple quickies are preferred over long sessions* If it's big, talk them through it* S*x is better with emotional connectionThe episode ends with a final thank you to the listeners and a look ahead to next week's show. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit dearblackgaymen.substack.com/subscribe
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Black Men Don't Lynch Ourselves
Sep 1801:29:38Tap to summarizeA Black man was lynched in America in 2025.Let me state, unequivocally, that this episode or us reacting to this story is not intended to position any person in this story as a member of the LGBTQIA+ community.But Demontre Reed was a Black man and to that end, he could have been me, or any of our listeners, or our brother, or our cousin, or our son. Regardless of his sexuality or ours, we, as Black men have a responsibility to this man’s life.So Tonight, I’m opening the conversation up from beginning to end as we answer one critical question, “where do we go from here” tonight on Dear Black Gay Men Podcast, and the show starts right now.We had a whole show tonight about dating.I don’t run away from the fact we talk sex on this platform, but I’ve been attempting to intentionally broaden our conversations beyond the bedroom.But I broke down today. I saw pictures of Tre Reed and got mad, then I got upset, then I got sad. So tonight, instead of keeping my feelings all bottled in, I want this to be a safe space for all of us to share whatever may be on our hearts.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.Chapters[00:00:01] Intro and the Death of Trey Reed[00:01:36] A Black Man's Life Lost[00:03:11] The Podcast's Purpose and History[00:04:19] Are We Ready for a Revolution?[00:06:04] Ads and Community Dialogue[00:10:39] The Proximity of Violence[00:15:37] The Desire for Retribution[00:16:34] Coincidences and Past Trauma[00:22:31] A List of the Fallen[00:25:28] The Role of Queer Leaders[00:31:51] Assimilation vs. Equity[00:44:09] Building a Community[00:56:39] Caller: Darren T[01:03:59] Caller: Antoine[01:18:47] Closing Comments and Future Plans This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit dearblackgaymen.substack.com/subscribe
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How To Set HEALTHY Dating Boundaries
Sep 1701:23:29Tap to summarizeBoundaries are simply what I say hell yea to.A good man will function well within your tolerable region without issue. And when he bumps up against your boundary, he’ll identify it, acknowledge, make good on the violation, and move on with a clearer understanding.But all of that is built on being clear about boundaries and that clarity, for most of us, comes long before we start dating anyone in particular.So tonight, we’re reacting to one tiktoker who breaks down boundaries, rules, and expectations in a way that we can apply to our dating lives.I want to know are we the drama with our ambiguous boundaries, or if niggas are just disrespectful because they ain’t s**t no way.Words like “boundaries” and “expectations” come up all throughout our dating life. A lot of the gworls think boundaries work and expectations just make room for disappointment.While that can be true, neither of those work unless we’re clear on our boundaries are, how we communicate them, and how we enforce them with love and grace.So tonight, Dr. Raquel Martin has got over a million-and-a-half views on TikTok, teaching us about boundaries. We’re reacting to this to see if there’s some Black gay wisdom we can take from the conversation.Chapters0:00:00 - The Road to Clear Boundaries0:01:50 - Boundaries, Rules, & Expectations: A Dating Guide0:02:53 - 4 Tips for Cuffing Season0:05:36 - The Private Party: Celebrating Jai's 40th0:08:22 - The Difference Between a Boundary, Rule, and a Standard0:14:38 - The Legacy of Tevin Campbell0:26:04 - Standards for Friends & The "Fence" Analogy0:41:43 - Why Black Gay Men Struggle with Intimacy0:52:49 - Disagreement vs. Argument: The Difference1:04:45 - Self-Knowledge vs. Self-Awareness1:13:04 - Listener Q&A: The Pain of Growth This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit dearblackgaymen.substack.com/subscribe
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Why Is Dating Black Men So Hard?
Sep 1601:15:38Tap to summarizeMy last relationship ended three times.The first time was because I was insecure. The second time was because he was impatient. The third time was because I never invested myself back into the relationship after the first two attempts.It takes a lot to see the dating process through to it’s hopeful end. Self-awareness is probably at the top of the list.So tonight, I’m asking the DBGM family to pull on our self-awareness. Each of us has to ask ourselves, “are we the drama?”Is dating actually hard, or do we make it that way?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.ChaptersDating as a Queer Person (00:00:01)The Problem with Dating (00:00:58)Church Announcements: Single Season as a Superpower (00:02:43)The Top Drought & Sexual Roles (00:10:20)Masculinity, Femininity, and Nuance (00:15:13)The Meaning of "Daddy" (00:46:14)The Need for Better Language (01:13:11) This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit dearblackgaymen.substack.com/subscribe
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Red Flags You Should Never Ignore
Sep 1201:04:59Tap to summarizeI believe that when we’re dating in our 30s, because we have something to lose, we try to safeguard our hearts and our lives from men that don’t mean for our good.That’s why red flags have become so important. We’ve seen our parent’s red flags when we were little. We’ve overlooked obvious red flags in our 20s. We’ve talked to our friends about their boyfriends red flags in our 30s.Everything in us is trying to avoid red flags and the headaches that come with them.So tonight, I’m talking red flags with one of the most unproblematic signs under the sun. He’s the writer, producer and star of one of my favorite web series, Love & Us. He’s come by the podcast as they prepare for the long awaited season 2.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.Chapters* 00:00:00 * 00:11:01: The "Top 5" segment begins, where the hosts and their guest discuss "Top 5 red flags that good sex will make you overlook."* 00:17:59: The hosts discuss a listener's question about HIV status as a red flag.* 00:20:23: The host asks listeners to share their absolute deal-breaker red flags in the comments during the break. * 00:21:36: The hosts review listener-submitted red flags from the comments.* 00:23:42: The hosts and guest discuss whether a person being HIV positive is a red flag, particularly if they are not undetectable. * 00:34:09: The guest discusses "red flags within ourselves," such as having tunnel vision about the type of person we want to date and missing out on other potential partners. * 00:37:34: The guest talks about their past experience of dating "just a little toxic" men who made them "chase them for their attention and affection." * 00:40:37: The host describes their own "Virgo red flag" of hyper-criticality, where they focus on fixing others' problems to avoid dealing with their own. * 00:45:57: The host asks about red flags in friendships, noting what he perceives as a "friendship epidemic" in Black queer culture where friendships are superficial and lack vulnerability. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit dearblackgaymen.substack.com/subscribe
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Why Gay Men Stay Single
Sep 1101:32:23Tap to summarizeEarlier this year, I dated someone for 6 months.I told my best friend about him after 3 months. He’d met my siblings after 5. On the face, it looked like things were progressing.The quiet truth is that he had dumped twice and I was too insecure to leave it alone when everyone around me told him he wasn’t the one.What I know about myself and so many others is that we, Black gay men, want to be in love. We want our person, but so many of us eligible bachelors are still in the dating pool.So tonight, I want us to really ask ourselves, is it me, or it it niggas that’s the problem?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.* Introduction: Dating Criteria and Finding the Right Man (00:00:01)* Welcome to Dear Black Gay Men Podcast (00:01:16)* Church Announcements and Personal Updates (00:02:42)* Wants vs. Needs in a Partner (00:04:53)* Sex and Emotional Connection in Dating (00:16:08)* Debate on the "Over-sexualization" of Black Men (00:20:23)* Acknowledging Both Sexuality and Personhood (00:39:15)* Conclusion: A Call for Broader Perspective (01:16:17) This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit dearblackgaymen.substack.com/subscribe
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What Makes a MAN Versatile?
Sep 901:27:04Tap to summarizeWhile I haven’t bottomed in a long time, most of my exes have been versatile.The irony, though, is that most of the problems and successes we faced in relationships stemmed from everything aside from what happens in the bedroom.Being verse, just like being top or bottom, can be limited to just dicks and asses, but I’ve found that for most of us, sexual position has some spill over into emotions, how we express our queerness, and how we’d like to be received by our partners.So tonight, let’s assume for a quick moment that there are two kinds of versatile. There’s sexual versatility and emotional versatility.I want to know if these two things exist. And if they both do, then how do we connect (1) connect with men that are the kind of vers that works with us, and (2) how do we steer clear of vers men that don’t.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.Chapters1. Introduction: Unpacking Versatility (00:00:01) The host, Jai The Gentleman, introduces the episode's topic: exploring versatility beyond just sexual positions.2. The Four Types of Verse (00:05:09) Jai explains the four types of versatile men based on his experience.3. Community and Criticism (00:08:14)4. Assumptions and Follow-Up Questions (00:13:52) The host poses a question to the audience: What is the first thing that comes to mind when a person says they are "verse"?5. "Total" vs. "Verse" (00:36:25) Jai explains his preference for dating versatile men over "total" tops or bottoms.He finds that people who use the word "total" to describe their position often have insecurities and focus on reinforcing boundaries he already respects15He feels that these individuals bring their insecurities into the bedroom, making the sexual experience about "f*****g parts and not people"He also criticizes tops who refuse to engage in oral sex, calling them "useless"176. Sexual Baggage and Vulnerability (00:41:22) The host discusses the baggage and insecurities some gay men carry, especially those who identify as masculine or "trade."7. Intentionality in Kink Spaces(00:58:43) Jai and a commenter discuss the lack of intentionality some Black men bring to kink spaces. He explains that since many in the community are "unaware of kink behavior," they don't know how to follow the "rules and regulations" of spaces like dark rooms20He gives examples of people using their phones with flashlights or turning on lights in a dark room, violating the intended purpose of the space21Jai advocates for more intentionality in how Black men explore their sexuality, so they can create more safe spaces for exploration.8. A Brooklyn Caller's Perspective (01:05:41) A caller named Donnie from Brooklyn, New York, joins the show.9. A Verse Caller’s Perspective (01:10:06) Nicholas and Jai discuss the parallels between sexual versatility and emotional intelligence.10. The Power of Versatile Men(01:14:42) Jai concludes the show by stating that he believes men who practice versatility are more emotionally aware and can teach the broader community how to balance masculine and feminine energy. He says that many Black men have a hard time being vulnerable and allowing themselves to be cared for, which is a skill that versatile men can help master. He believes that versatile men are meant to help the gay community evolve into a "better group of people". This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit dearblackgaymen.substack.com/subscribe
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Are The Real Tops Gone?
Sep 501:22:02Tap to summarizeI am what the gworls would call a “soft top”.I like to do all the traditionally masculine things, but I also am fully a butch queen. I haven’t been fucked in years and don’t have a whole lot of interest in being fucked, but I would for the right person as long as they know how to handle my delicate flower.Fun Fact: someone once called it a slut with my dick but a prude with my hole.1. The Top Drought (00:00:00)2. Church Announcements: The Blog and a Hookup Story (00:01:52)3. Understanding Bottom’s Non-Verbal Cues (00:08:52)4. Critiquing Queer Culture and Fetishization (00:41:52)5. The Fetishization of Masculinity (00:22:52)6. The Evolution of Queer Identities (00:55:14)7. The Dangers of Narrow Definitions (00:30:02)8. The Four Kinds of Vers (01:16:19)9. Patriarchy in Queer Relationships (01:05:06)10. The Value of Sex and Self-Awareness (01:19:05) This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit dearblackgaymen.substack.com/subscribe
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WORK WORK WORK (in my Rihanna voice)
Aug 2, 2023Tap to summarizeHave you ever met a guy, got a number, texted for a while, a couple dates, but just can't make it over the 90-day hump? After so many failed dating attempts, it's easy to think it's either all men...or it's got to be me.This episode of the podcast is here to show us that it's a little of column A, a little of column B. A whole lot of luck and the right kind of work. What kind of work should we be putting into our dating situations? And how to ensure that work pays off?Special thanks to @infiniteimani3534 for the inspo, and comments from @YzBG and http://www.instagram.com/alexanderlove_love➡️ Become an Insider: http://www.dearblackgaymen/subscribe➡️ Join the newsletter: http://www.dearblackgaymen.com/weekly This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit dearblackgaymen.substack.com/subscribe
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