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PODCAST

Dear Black Gay Men Podcast

Jai The Gentleman

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

society & culture relationships

All Episodes

78:11

Is the Dating Pool Trash, or Are We the Drama? 🤔

Dear Black Gay Men Podcast ·

2025/11/25

The latest episode of the Dear Black Gay Men Podcast tackles a question burning up the timelines: Is the dating pool really trash, or are we, the daters, the drama? Host Jai the Gentleman dives deep into this topic, reacting to the recent vlog, “32 and Dating is Trash,” by vlogger DearDondre.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

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74:36

🎙️ Jess Hilarious Drama & Queer Culture’s Power: A...

Dear Black Gay Men Podcast ·

2025/11/19

The drama surrounding Jess Hilarious’s controversial comments about who can have babies and her subsequent firing from the Ms. Pat Settles It show is the main event on the latest episode of the Dear Black Gay Men Podcast. 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.🛑 Why Jess Hilarious Can’t “Shut The F**k Up”Jess Hilarious first sparked controversy with her “who’s looking out

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75:19

Lies, Love, and the “Trash” in Queer Culture

Dear Black Gay Men Podcast ·

2025/11/18

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.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.Are We Really “Trash”?I challenge the idea that our culture is “trash.” While acknowledging that

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79:11

From Pulpit to P*rn: Mourning Michael Hurd and...

Dear Black Gay Men Podcast ·

2025/11/14

This episode of Dear Black Gay Men Podcast, host Jai the Gentleman tackles two sensitive but vital issues for the Black queer community: grieving a polarizing figure and the complicated discussion around trans identity.🕊️ Remembering Michael Hurd: Yes King, Pastor, and ManThe community lost Michael Hurd, also known as Love and Light TV or Yes King, who passed away suddenly at 47. Michael was a prominent Black gay man, a father, and an entrepreneur who sparked conversations about spirituality and

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77:30

The App Trap and the Cookout Conundrum: Real Talk on...

Dear Black Gay Men Podcast ·

2025/11/13

On this episode of Dear Black Gay Men Podcast, host Jai the Gentleman tackles two viral topics: the toxic truth about dating apps for Black gay men and the ever-controversial question of white presence in Black spaces.📱 Dating Apps: Good for What?We often say the dating pool is trash, but Jai argues we really mean the “app dating pool is trash”. Why is it such a struggle? The app landscape is split into three main groups:* People looking for genuine love.* People only looking to hook up.* The

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85:17

Masculinity, Femininity, and Everything In Between:...

Dear Black Gay Men Podcast ·

2025/11/12

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 all the time” are “fighting against something”. He’s clear that he loves men who express in every version

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75:25

Top-Tier Men, Dating Lies, and the Evolution of...

Dear Black Gay Men Podcast ·

2025/11/07

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,” suggesting this ideal is often “hetero adjacent” and “straight acting”.Jai’s personal preference leans toward

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83:42

Good Boys, Bad Boys, and Toxic Exes: Where Does...

Dear Black Gay Men Podcast ·

2025/11/04

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:* Bratty Subs: Seven men preferred a Dom who would “put them in their place” and actively dominate them.*

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59:08

Why Black Gay Men MUST Vote, and the Queer Candidate...

Dear Black Gay Men Podcast ·

2025/10/30

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 when your community needs you.This is a must-read if you’re tired of the noise and ready to talk about the

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77:12

"Chosen Singleness": Why Eligible Black Gay Men Are...

Dear Black Gay Men Podcast ·

2025/10/29

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 JobHost Jai The Gentleman interviewed 20 eligible Black single men, defining “eligible” as having a crib (paying rent/mortgage), a car (access to

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76:13

Fragile Masculinity, DL Whisperer, & Why Straight Men...

Dear Black Gay Men Podcast ·

2025/10/23

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 Episode, We Tackle:* The DL Whisperer & “Clocking Trade”: JAI reacts to the backlash against the

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78:12

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

Dear Black Gay Men Podcast ·

2025/10/22

From Depression to Desire: Kid Fury is Back and We’re Talking Dating, Catcalls, and Black Male BeautyAre 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 reacting to the highly anticipated return of internet icon, Kid Fury, whose first upload in a decade, “One

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83:12

Decoding “Daddy”: Beyond the Bedroom in Black Gay...

Dear Black Gay Men Podcast ·

2025/10/15

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 dick, or does it come with a level of real-life responsibility?JAI even shares an exclusive update about his

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66:41

I Obsessed Over Getting Men To Commit in...

Dear Black Gay Men Podcast ·

2025/09/30

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 concretely say why.* 🗣️ The three simple considerations men make when deciding to take dating to the next level:

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83:18

I Obsessed Over Being a Better Top (here's what I...

Dear Black Gay Men Podcast ·

2025/09/25

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 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

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89:38

Black Men Don't Lynch Ourselves

Dear Black Gay Men Podcast ·

2025/09/18

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 Black men have a responsibility to this man’s life.So Tonight, I’m opening the conversation up from

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83:29

How To Set HEALTHY Dating Boundaries

Dear Black Gay Men Podcast ·

2025/09/17

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 particular.So tonight, we’re reacting to one tiktoker who breaks down boundaries, rules, and expectations

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75:38

Why Is Dating Black Men So Hard?

Dear Black Gay Men Podcast ·

2025/09/16

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 pull on our self-awareness. Each of us has to ask ourselves, “are we the drama?”Is dating actually hard, or

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64:59

Red Flags You Should Never Ignore

Dear Black Gay Men Podcast ·

2025/09/12

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 us is trying to avoid red flags and the headaches that come with them.So tonight, I’m talking red flags

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92:23

Why Gay Men Stay Single

Dear Black Gay Men Podcast ·

2025/09/11

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 in love. We want our person, but so many of us eligible bachelors are still in the dating pool.So tonight, I

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143 results

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