Late Night with Sylvester

Late Night with Sylvester

Late Night with Sylvester is a podcast that friends get together and talk real shit about day to day life, sex, relationship and even work life. With a cup full of truth and teaspoon of shade.

Episodes

May 30, 2026 18 mins

In this episode, I'm catching you up on my day and everything that's been on my mind lately. I talk about my trips to DC to spend time with a man I really like, and how I'm trying to be more intentional about dating, relationships, and where I invest my energy.

I also get into some real-life adulting after finding out my rent is increasing. 

And as if life wasn't busy enough, I'm also getting ready for my upc...

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In this episode, I’m fresh out of the shower and fresh in my thoughts. I start off talking about RHOA — who I’m liking so far and what’s not really working for me when it comes to the production and some of these scenes.

Then I get into my week, including seeing the man I’ve been trying to get over… yeah, we need to talk about that.

I also share my thoughts on dating shows like Pop the Balloon, Find Queer Love, and Shoot Your Shot We...

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April 17, 2026 71 mins

This one’s dedicated to Wendy Williams! I was inspired after watching her biopic, so I was giving full radio vibes—playing music, talking my feelings, and catching a whole mood. I’m still high off my Turks and Caicos trip, and I went live on BIGO during this one. I opened up about my relationship situation—how I’m feeling, what’s next, and getting ready to move forward. It was real, and it was fun. Plus, every time I had to do some...

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Mark as Played
April 10, 2026 23 mins

Thank you for stopping by and listening to another episode of Late Night with Sylvester. This episode I talked about the recent Nene Leakes interview with Carlos King, where shit got real and Bravo owes my girl a CHECK. I also mentioned wanting some new d**k and my situation with "Daddy Wes." There are some challenges. As the episode unfolds, I posed a question to the listeners: Am I wrong for wanting the homie too? LOL

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April 6, 2026 36 mins

In this episode, I’m giving you a full recap of my trip to Turks and baby, it was a time. From the vibes to the moments, I had so much fun being outside, enjoying the sun, and just living.

But let’s be real… the gurls were giving a little mean girl energy while I was there, and I had to clock that.

And then… I get to a point where I almost hook up with a friend of a friend. Yes, I almost made a decision, but thank God I didn’t. Somet...

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Mark as Played
March 23, 2026 55 mins

In this episode, I’m recapping my weekend and getting into everything leading up to my upcoming trip to Turks and Caicos, because I’m outside and preparing.

While recording this episode, I went live on BIGO, bringing y’all into the moment with me in real time. The energy was fun, a little interactive.

Between weekend vibes, travel prep, going live, and a little cultural commentary, this episode is a mix of real life, reflection, and ...

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Mark as Played
March 14, 2026 29 mins

In this episode, I’m catching you up on my week. The weather has been beautiful the past few days, and you already know how everyone starts acting differently the moment the sun comes out. When winter breaks for a second, suddenly everybody is outside, in a good mood, and living their best life.

I also talk about getting my PrEP shot this week and why taking care of your health is so important. We’ve come a long way when it comes to...

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March 5, 2026 20 mins

In this episode, I talk about my journey with PrEP and getting ready for a new PrEP option that will be a bi-annual shot. Taking care of my health has been an important part of my life, and I share a little about what that process has looked like for me.

I also talk about my busy week at work and how things have been moving lately. Then I get into my weekend, which I spent with a familiar gentleman — and let’s just say it was a vibe...

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February 21, 2026 24 mins

In this episode, I start off talking a little RHOP and sharing my thoughts on some of the women, because you know I have some thoughts.

Then the conversation shifts into something more personal. I share a little about my situation with a man I know and love, giving background on my feelings and what’s really been weighing on my mind.

Sometimes you reach a point where you have to address what’s been sitting in your heart. This episode...

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February 12, 2026 29 mins

In this episode, I start off talking about those Black queer dating show spinoffs and why being unique is a must. Then, I get into my weekend in Atlanta—yes, it was a vibe—until I had a less-than-cute experience at the Morehouse bookstore. We end the show on that note—because even the best weekends have a little drama.

Don’t forget to subscribe, like, and give me my 10s in the comments!

X: @LNwithSylvester

Email: LateNightwithSylvest...

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February 5, 2026 46 mins

This week, I break down my weekend adventures, including a night out with my friend that left me feeling a little… embarrassed. And then I get to a crucial topic: are you a glass drinker or a plastic cup drinker? Because, let me tell you—there’s a difference, and I’m all about the glass. Join me as I share my perspective, laughs, and a little weekend reflection.


 Don’t forget to subscribe, like, and give me my 10s in the comme...

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Mark as Played
January 17, 2026 38 mins

In this episode, I’m breaking down my weekend in Dallas — starting with a crazy altercation that happened on the very first day of the year. It was unexpected, intense, and definitely tested my patience.

I use that moment to talk about the importance of truly knowing yourself, staying in control, and not letting other people’s chaos knock you out of alignment. Because growth isn’t about avoiding conflict — it’s about how you handle ...

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January 11, 2026 27 mins

In this episode, I’m talking through my day and getting honest about some red flags I’m noticing with a guy I’ve been spending time with. I’m not sure he’s my person, and instead of forcing it, I sit with that feeling and unpack what I actually want.

I talk about the kind of man I’m drawn to, why dating older men feels attractive to me, and how clarity starts showing up when you’re finally listening to yourself. In the middle of it ...

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December 5, 2025 32 mins

This week, I’m getting into the stress and excitement of planning my birthday trip to Dallas, including trying to find a place to stay. Between all the options and my standards, I’m starting to wonder if I’m too picky… but honestly, I’ve earned it.

I also touch on a small issue at work before getting into how cute (and chaotic) my weekend really was. My best friend proposed to her girlfriend, love was absolutely in the air. I went t...

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Mark as Played
November 27, 2025 33 mins

In this episode, I’m recapping my weekend — and it had range. Saturday kicked off with a Friendsgiving that started calmly and quickly turned chaotic, setting the tone for the night.

On Sunday, I slowed things down a bit: cleaned my place, reset my space, and then headed out to a rooftop party. From there, I talk about my interactions with men that night — including why men in their 40s are actually so sexy. Confidence, emotional se...

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November 19, 2025 34 mins

This week, I’m giving you a cute Sunday recap of my weekend in the city. Friday night was a whole vibe — the host let me into the party smooth as hell, and it set the tone for the evening. Saturday had me in Brooklyn all day, soaking up the energy, the people, the everything.

I also get into a topic that’s been on my mind: dating outside of your income level. Is it a problem? Is it messy? Is it realistic? I have some thoughts, and y...

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November 6, 2025 20 mins

This week, I’m in a great space — life’s moving in the right direction, and it feels good to say that out loud. I talk about no longer needing to work my part-time job, how freeing that’s been, and the importance of decluttering — not just my space, but my energy and the people around me.

I also get into why it’s weird when people act like they don’t see you out, but eventually, I’ll speak. And of course, I share some love from my m...

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October 24, 2025 24 mins

This week, I had to get a few things off my chest — literally and figuratively. I talk about my recent experience going to a sex party and what really goes down at those events. From the atmosphere to the energy, I share what I liked, what I didn’t, and why I’d love to throw my own exclusive, high-level version — a space that’s sexy, safe, and way better than what’s out there now.

It’s candid, it’s bold, and it’s definitely not for ...

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Mark as Played
October 16, 2025 17 mins

This week, I’m back after being down bad with the flu — and baby, it had me out. While I was recovering, a man decided to shoot his shot, and let’s just say… it reminded me why I keep my standards high. I get into what the bare minimum looks like to me when it comes to dating, and why showing up with effort will always be attractive.

It’s honesty, humor, and a little shade — all in one episode.


 Don’t forget to subscribe, like,...

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September 24, 2025 27 mins

This week, I cover it all — from the wild dream I had about someone’s best friend (is that good or bad? 👀) to finally getting my full-time offer. I discuss what it’s like being a big brother who sometimes feels more like a parent, and I even call my grandmother live on the show to wish her a Happy 89th Birthday.

Of course, I had to get into the topic of men and their insecurities — because, let’s be honest, insecure men always end ...

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Mark as Played

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