Jai The Gentleman

Dear Black Gay Men Podcast

Society EN ↓ 134 episodes

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

Author

Jai The Gentleman

Category

Society

Latest episode

May 28, 2026

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Episodes

Masculinity, Femininity, and Everything In Between: Unpacking Preference on Dear Black Gay Men Podcast 12.11.2025

We’re diving deep into a topic that sparks major conversation in our community: masc for masc culture and the complexities of preference, identity, and stigma. Host Jai the Gentleman kicks off the episode by sharing his own preference for “girly boys” and feminine men, playfully stating, “nothing is too feminine for me”. He admits to being “the drama” for feeling that gay men who are “masculine al...

Top-Tier Men, Dating Lies, and the Evolution of Self-Love 07.11.2025

The latest episode of the “Dear Black Gay Men Podcast” dives headfirst into the hot-button topic of the “top-tier man” in gay culture. Host Jai the Gentleman kicks off the discussion by reacting to a SaySoTV video that identified a man as “tall, dark, and fluid” and “top-tier”. Jai questions the widely held assumption that a “top-tier man” is simply a “heterosexual man that likes other men,” sugge...

Good Boys, Bad Boys, and Toxic Exes: Where Does Persistence Become Harassment? 04.11.2025

The latest episode of the Dear Black Gay Men Podcast with Jai The Gentleman dove headfirst into the nuanced world of dominance, submission, and the sticky dynamics of dating in the black queer community. The central conversation explored the concept of the “good boy”, and how subs prefer to be handled in black queer culture. Based on a poll of 20 self-professed “good boys,” the results were split:...

Why Black Gay Men MUST Vote, and the Queer Candidate Shaking Up Alabama 30.10.2025

We had to put the dating talk aside for a night because, frankly, the times are serious. Election Day (November 4th) is right around the corner, and the stakes couldn’t be higher. We were honored to have Dakarai Larriett , candidate for Alabama’s open U.S. Senate seat, join us in The Backroom to talk about fighting hopelessness, confronting political gridlock, and what it truly means to step up wh...

"Chosen Singleness": Why Eligible Black Gay Men Are Done with Dating 29.10.2025

Are Black Gay Men Actively Choosing to Stay Single? On a recent episode of the Dear Black Gay Men Podcast , we dove deep into a question that’s been bubbling: Why are so many eligible Black gay men opting for “chosen singleness” instead of cuffing up? The answers might surprise you, but they definitely hit home. The Big Experiment: Crib, Car, and a Job Host Jai The Gentleman interviewed 20 eligibl...

Fragile Masculinity, DL Whisperer, & Why Straight Men Can't Clock a Queen 23.10.2025

In this unfiltered and necessary conversation, host JAI The Gentleman dives headfirst into the hot-button issues shaking the Black queer community: the toxic allure of the “DL Whisperer” and the explosive viral video on “fragile masculinity.” This is the deep-dive talk every Black gay man and our allies need to hear about honesty, safety, and cultural responsibility in dating. In This Must-Listen...

Kid Fury's Return, Blind Dating, and the "I Love You" Barrier 22.10.2025

From Depression to Desire: Kid Fury is Back and We’re Talking Dating, Catcalls, and Black Male Beauty Are You Stuck in a Sad Boy Shell? Kid Fury and the Dear Black Gay Men Podcast Host Say Get Outside! The latest episode of the Dear Black Gay Men podcast, hosted by Jai the Gentleman , is a must-listen for Black queer men navigating life, dating, and mental health. This week, Jai the Gentleman is r...

Decoding “Daddy”: Beyond the Bedroom in Black Gay Culture 15.10.2025

Join JAI The Gentleman of the Dear Black Gay Men Podcast as he breaks down an exclusive, off-air conversation from the “Private Party” episode and dives into the ambiguity of this cultural term. In this episode, we tackle the big questions: * Does “daddy” have a meaning outside of sex in Black gay culture? * Does the term lose its meaning when we use it too often? * Is it simply a top with a big d...

I Obsessed Over Getting Men To Commit in Relationships (here’s what I learned) 30.09.2025

I interviewed 20 eligible single men to find out the real reasons they don’t commit. This episode of the Dear Black Gay Men Podcast unpacks the surprisingly consistent dating horror stories and boils them down to three basic things every man needs to commit to a relationship. In this video, you’ll learn: * 🔑 The number one reason men don’t commit: they don’t know what they want, or can’t concrete...

I Obsessed Over Being a Better Top (here's what I learned) 25.09.2025

I 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 sex Whether 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 cha...

Black Men Don't Lynch Ourselves 18.09.2025

A 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 Bl...

How To Set HEALTHY Dating Boundaries 17.09.2025

Boundaries 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...

Why Is Dating Black Men So Hard? 16.09.2025

My 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...

Red Flags You Should Never Ignore 12.09.2025

I 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...

Why Gay Men Stay Single 11.09.2025

Earlier 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 i...

What Makes a MAN Versatile? 09.09.2025

While 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,...

Are The Real Tops Gone? 05.09.2025

I 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 D...

Why Do We Sexualize EVERYTHING? 29.08.2025

I like being naked. I like being naked with other men. And I like being naked when sex has nothing to do with it…but it can. I call that being a nudist, but sometimes terms like kink, or nudist, or voyeur don’t resonate with Black men. But can they? Or should they? So tonight, I’m joined by the promoter behind the biggest wave of nudist club nights for cis men by a Black promoter. I’ve attended hi...

Where Do Trans Men Fit in Gay Pride? 27.08.2025

When I walk into any pride celebration, there are a couple things that connect me and most of the men present. Number 1: we’re all men and Number 2: we’re attracted to men. But what happens when only one of those apply to all of us and how do we create pride celebrations that affirm all of our experiences. So tonight I’m joined by A’Jay Love . He’s a trans masc creator who gained prominence when h...

I Interviewed 50 Couples. Here's What No One Tells Us About Dating 30.07.2025

These couples uncover the secrets to successfully navigating the dating pool as I abruptly find myself back in it. * 00:00:00 - Introduction: Three Rules for Finding a Man * 00:01:11 - Applying the Lessons & Welcome * 00:02:02 - Personal Update: Dealing with a Breakup * 00:04:50 - The Danger of Denying Emotions After a Breakup * 00:09:25 - Finding a Good Man: Setting Intention * 00:11:02 - Differe...

How Black Gay Men Find Chosen Family While Living With HIV 04.07.2025

This week, Jai The Gentleman connects with Daniel Driffin Chapters 0:00:00 - Introduction to the guest, Dr. Daniel Driffin 0:01:51 - Discussion on the CRIBB program 0:11:09 - NAESM as family, friends, and a brave space 0:12:01 - The need for affirmation within the Black queer culture 0:22:52 - The significance of the changing language and the future of black queer culture 0:26:06 - Personal signif...

Why Good Men Love Open Relationships (while 70% of everyone else calls it cheating) 02.07.2025

My inadequacies around relationship stemmed from times when my feelings were disregarded. I learned, having been on the receiving end of emotional trauma, that there are three basic agreements at work in any relationship. Nailing these will help quell the inadequacies and insecurities so many of us experience in our partners, and make way for clear agreements that both (or all) involved can be com...

I Came Out...to My P*nis 11.06.2025

This week Jai The Gentleman discusses: How "coming out" goes way further than just telling people you're gay. It's an everyday process that starts with yourself. NEW CONTENT, every day on YT : youtube.com/@dearblackgaymen Subscribe to second channel: youtube.com/@jaithegentleman Shop Brand New Merch: https://dearblackgaymen.shop Listen on Spotify: https://spoti.fi/3CvMjTh Listen on Apple Podcasts:...

I Found My Boyfriend...Then My Life Fell Apart 28.05.2025

This week Jai The Gentleman discusses the last relationship he was in and how Black queer culture tried to destroy it. And how you can safeguard your relationship from the triggers that come from the gworls. 00:00 Introduction to Black Gay Culture and Relationships 01:04 Welcome to Dear Black Gay Men Podcast 0 1:47 Personal Dating Experiences and Vulnerability 03:11 Church Announcements and Upcomi...

3 Signs Your Black Gay Romance is the Real Deal 07.05.2025

Read “I made 6 guys cum at the park” https://bit.ly/4jFmRx3 Chapters 00:00 The Importance of Sex in Relationships 00:57 Introduction to the Podcast 01:56 Church Announcements 04:21 Signs of a Healthy Relationship 08:35 The Complexity of Relationships 13:24 Conclusion and Final Thoughts ➡️ Shop DBGM Merch: https://www.dearblackgaymen.shop   ➡️ Become an Insider: https://youtube.com/@dearblackgaymen...

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