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

"I don't know how you feel 'til you tell me" 07.06.2023

Talking to a new guy is the part of dating that is the most exciting because you get to figure out the guy and dream about your future together. But with that can come some tense discussions. This week's episode is dedicated to understanding where those arguments come from when you're dating, how to get out of them, and the self-work Black gay guys have to do to avoid them altogether. #dating #rel...

Just ask him out! 31.05.2023

Asking someone on a date seems pretty simple, but so many Black gay guys fail (or suck) at it, even in 2023. In this episode,  @jaithegentleman  gives his short, 3 step process to asking anyone on date and getting them to say yes. If you want to get the date with the guy you've been eyeing across the bar, gym, supermarket, or app, this episode was made specifically for you. #dating #relationshipad...

He got on and left yo *ss for a white gworl 24.05.2023

We go live Thursdays at 9pm EST! Join the group: https://bit.ly/3wsiWx4 Listen to the podcast: https://tinyurl.com/5ymdtdx4 The best part about talking to so many gay guys about dating is that I can start to see the patterns. Every time the conversation of prominent interracial couples comes up, I see a patter. I could be biased, but there is an equation that makes interracial dating work for some...

Ain't you tired? 17.05.2023

This episode was therapy for me. It took actual therapy, a failed Jack'd encounter, and some introspection for me to see one of my deepest issues in dating. Enjoy. New uploads THURSDAYS Join the group: https://bit.ly/3wsiWx4 Listen to the podcast: https://tinyurl.com/5ymdtdx4 ➡️ Join Dear Black Gay Men Insiders for exclusive content FB Group: https:// bit.ly/3wsiWx4 📲 Subscribe to Dear Black Gay...

Church shouts and c*m dumps 19.04.2023

Saturday night at a sex party-->Sunday morning at church-->Monday afternoon epiphany moments. New uploads THURSDAYS Join the group: https://bit.ly/3wsiWx4 Listen to the podcast: https://tinyurl.com/5ymdtdx4 ➡️ Join Dear Black Gay Men Insiders for exclusive content FB Group: https:// bit.ly/3wsiWx4 📲 Subscribe to Dear Black Gay Men Podcast Apple: https://tinyurl.com/5ymdtdx4 Spotify: https:/...

Trust the process 12.04.2023

It's crazy that a trip to the mall, ten years ago, with my ex-boyfriend Thomas would lead me to this aha moment at my big-big-age. New episodes WEDNESDAYS Join the group: https://bit.ly/3wsiWx4 Listen to the podcast: https://tinyurl.com/5ymdtdx4 ➡️ Join Dear Black Gay Men Insiders for exclusive content FB Group: https:// bit.ly/3wsiWx4 📲 Subscribe to Dear Black Gay Men Podcast Apple: https://tiny...

S*x, courage, and vulnerability 29.03.2023

I had horrible s*x with two people that taught me some huge lessons. New episodes WEDNESDAYS Join the group: https://bit.ly/3wsiWx4 Listen to the podcast: https://tinyurl.com/5ymdtdx4 ➡️ Join Dear Black Gay Men Insiders for exclusive content FB Group: https:// bit.ly/3wsiWx4 📲 Subscribe to Dear Black Gay Men Podcast Apple: https://tinyurl.com/5ymdtdx4 Spotify: https://tinyurl.com/2p9pye7s YT: htt...

My d*ck needs more 5 star reviews 22.03.2023

I asked a simple question about sex in the group and we jumped in the comments to give our pair of pennies. But what came up was a discussion about self, connection and relationship that I didn't expect. This episode is particularly significant for me because it marks our 50th episode of the podcast. As you can tell, I record these days--sometimes, weeks--in advance. But my gratitude to you all fo...

I was just a piece of d*ck to him 15.03.2023

Have you ever heard something that sounded right, but it took you a little while before you actually got the lesson? That was me in this conversation with Hakim Asadi . He talked about closure in one of my last episodes of Dear Black Gay Men Live in 2022. But it wasn't until recently where I totally got the lesson. ➡️ Join Dear Black Gay Men Insiders for exclusive content FB Group: https:// bit.ly...

The equation for the PERFECT FIRST DATE 08.03.2023

I asked this question the other day about first dates, hopefully attempting to get some clarity on how to have better ones. Then I remember, "I'm the FIRST DATE GURU". Full disclosure, though, I am rarely asked out on a first date. So as I was thinking about what I hope he's going to do, I realized there is a fool proof equation to making a first date memorable. ➡️ Join Dear Black Gay Men Insiders...

Dating on the Auction Block 01.03.2023

First, thank you to all our listeners and subscribers. We're coming up on 7500 monthly downloads. For a new show that's only 15 minutes long, that's a BIG DEAL. Then, I had a conversation with a friend of mine who we'll call "Oscar". He said something--responded to something I mentioned in a previous episode--and that conversation made think. ➡️ Join Dear Black Gay Men Insiders for exclusive conte...

"Talking to" vs. "Dating" 22.02.2023

I asked this question in our Dear Black Gay Men Insiders group and the conversation was...interesting. Somehow "talking to" became the plot...perpetrated by Millenials...to get us caught up IN THE BULLSH!T. Oddly enough, I think the "talking to" phase is critical to dating. This episode is my argument why. ➡️ Join Dear Black Gay Men Insiders for exclusive content FB Group: https:// bit.ly/3wsiWx4...

We can commit to douching but we can't commit to eachother? 15.02.2023

I asked this question about talking to someone and got so many responses about commitment. Reading through got me to thinking about a particular minister that I used to crush on...and why I used to crush on him. #JudgeMeLater, but this is what I learned. ➡️ Join Dear Black Gay Men Insiders for exclusive content FB Group: bit.ly/3wsiWx4 📲 Subscribe to Dear Black Gay Men Podcast Apple: https://tiny...

Shut up...I'm trying to hear what his bussy is saying 08.02.2023

I've interviewed bottoms asking them what they wish tops understood . Then last week, I talked to a top who had his own "things bottoms should know". But, this is my take as a vers who doesn't bottom that often. #JudgeMeLater ➡️ Join Dear Black Gay Men Insiders for exclusive content FB: bit.ly/3wsiWx4 📲 Subscribe to Dear Black Gay Men Podcast Apple: https://tinyurl.com/5ymdtdx4 Spotify: https://t...

So this what the mean by "take your time"? 01.02.2023

You go out on a date, what do you expect the next day? A good morning text? Some sweet nothings in your DMs? That was me, secretly wanting him to fawn over me on date two. But this date with "Brandon" is changing all of that for me. Back again with some #firstdatechronicles. He and I went out a couple weeks ago, but instead of feeling left behind and jilted, I'm still in my feels because Brandon i...

Dating Stank...do not recommend 18.01.2023

I advocate for the single life because a purposeful single life leads to purposeful, fulfilling relationships. I learned that lesson from a whole host of failed dating attempts. These are the nuggets I picked up along the way. Links: https://www.instagram.com/DearBlackGayMen https://www.instagram.com/JaiTheGentleman http://www.dearblackgaymen.com Theme music by The Passion HIFI This is a public ep...

Another failed dating attempt 11.01.2023

If nothing else, I am consistent. Stood up for a date so I started a podcast. Stood up again by the same dude, must mean season 2. Another failed dating attempt, must mean it's time to get back to work. Thanks universe. Links: https://www.instagram.com/DearBlackGayMen https://www.instagram.com/JaiTheGentleman http://www.dearblackgaymen .com Theme music by The Passion HIFI This is a public episode....

I told him, "Bring me that a$$. Tonight at 10." 07.12.2022

It was an ass appointment that reminded me of a preacher with a Jheri curl. Long story, but a good lesson. Dear Black Gay Men Live: https://bit.ly/3UfQSqh Links: https://www.instagram.com/DearBlackGayMen https://www.instagram.com/JaiTheGentleman http://www.dearblackgaymen .com Theme music by The Passion HIFI This is a public episode. If you'd like to discuss this with other subscribers or get acce...

New phone...who dis? 30.11.2022

If you’ve ever been ghosted, it can be hard to pick up the pieces especially if you were really cutting for this man. When I got ghosted, luckily, I knew it was his loss, but it still hurt. This is my story. Hopefully you can relate. Magic Mind: https://www.magicmind.co/dbgm   Use code “DBGM20” for 40% off your subscription (limited time offer) Links: https://www.instagram.com/DearBlackGayMen http...

“I get so excited…you know how I like it…” 23.11.2022

I’ve dated men who were EXCITING and that made me EXCITED to be around them. Then I dated men who were just a date. Because I’ve been on both ends of the excited-ness spectrum, I’m pretty good at pulling out some hallmarks to know when he’s actually excited about you, or if it’s just a show. Magic Mind: https://www.magicmind.co/dbgm   Use code “DBGM20” for 40% off your subscription (limited time o...

I’m guilty of gaslighting 16.11.2022

Even though I’m healed now, I’m guilty as anyone else of hurting people in my past. This episode is my story of figuring out what gaslighting is, how I gaslit my ex, and what I did to overcome it—my healing process. Magic Mind: https://www.magicmind.co/dbgm  Use code “DBGM20” for 40% off your subscription (limited time offer) 3 Unmistakeable Signs He’s Gaslighting You:  https://youtu.be/zejx5Eisdj...

Broke up...now it's time to move on, sis 09.11.2022

After recording this one, I've realized that I dedicated a lot of energy to "Joe" for one reason. This episode, I'm talking through how I learned that it's way past time to move on. 📲 Subscribe to Dear Black Gay Men Podcast Apple: https://tinyurl.com/5ymdtdx4 Spotify: https://tinyurl.com/2p9pye7s YT: https://bit.ly/3VerZNj 🎶 Theme music by The Passion HIFI Our purpose is to be the voice of our c...

I quit, bruh. No really... 02.11.2022

I be quitting s**t. Quitting people, quitting projects, quitting everything I've set my mind to. Well, not everything, but a lot of stuff. So I'm talking about how I'm not quitting this season and the lessons I'm learning by persevering. 📲 Subscribe to Dear Black Gay Men Podcast Apple: https://tinyurl.com/5ymdtdx4 Spotify: https://tinyurl.com/2p9pye7s YT: https://bit.ly/3VerZNj 🎶 Theme music by...

Cheater Cheater Pumpkin Eater 26.10.2022

📲 Subscribe to Dear Black Gay Men Podcast YT: https://bit.ly/3VerZNj Apple: https://tinyurl.com/5ymdtdx4 Spotify: https://tinyurl.com/2p9pye7s 🎶 Theme music by The Passion HIFI Our purpose is to be the voice of our culture: talking to Black gay men, about Black gay men and for Black gay men in ways that thinks us forward. I had an ex, Terry, who taught me the most valuable lesson of all: cheatin...

Hi, my name is... 19.10.2022

The most random conversation in the DMs gave me two HUGE insights on my own dating life and our culture. Spoiler Alert: you may want to stay out my DMs. #SingleLife #Identification #RepresentationMatters #DatingAdvice #SingleAdvocate 📲 Subscribe to Dear Black Gay Men Podcast YT: https://bit.ly/3V8HjuW Apple: https://tinyurl.com/5ymdtdx4 Spotify: https://tinyurl.com/2p9pye7s 🎶 Theme music by The...

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