Late Night with Sylvester

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...

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...

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...

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 ...

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.

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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 ...

This week, I’m sharing what my weekend was like — most of it spent going out by myself, and honestly? It’s been fun. There’s something freeing about getting dressed up, hitting the scene solo, and doing exactly what I want.

I also get into an interaction I had at the bar that reminded me why going out alone can be just as interesting as going out with a crew.

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This week, I’m back from my Atlanta trip, and I have stories to tell. With a $500 budget, I thought I’d land a decent hotel, but Atlanta had other plans — and let’s just say the experience was not giving. I break down the highs and lows of my stay, the parties I hit while I was there, and why I had to cut the trip short and come back early.

From budgeting blues to nightlife adventures, this episode is all about lessons learned and m...

This week, I’m getting ready for my trip to Atlanta, and the excitement is real! While I pack, I get into the very real struggle of sleeping next to snorers — because let’s be clear, I just can’t do it. I also share my experience at a TS Madison event and what it meant to see her doing her thing in the spotlight.

From travel plans to pet peeves to unforgettable moments, this episode has a little bit of everything.

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This week, I’m celebrating something big — I finally got my new car, and the excitement is real! But that’s not all I’m talking about. I get into a conversation I had on X about what it means to give up a little control in a relationship — especially in a gay relationship — and why it’s okay to admit you need a man.

I dive into the importance of men stepping up as providers, the balance between strength and surrender, and how wantin...

This week, I’m talking about a smoke session that went all the way left when a friend came over… dirty. Hygiene is a must when you’re dealing with me, and I’m not shy about saying it. I also get into the high standards I keep for men who try to approach or flirt with me — because not everyone can sit at my table.

I share a little about my beach day, soaking up the summer sun, and give you the latest twists in my messy situationship....

It’s still Pride Month, and Sylvester is still outside — but the car drama? Still dragging. In this episode, you’ll hear all about the nonsense that comes with car shopping (or the lack thereof), the moments that waste your time, and some real talk about what’s happening in the world — from trans rights to immigration.

It’s a reminder that identity, community, and joy still matter — even when everything else feels heavy. And as alwa...

You were just trying to have a good time — celebrating Pride, vibing with your crew, and getting on with your fabulous business. But then she tried it. In this episode, you’ll relive the highs of a wild Pride weekend and hear what really went down at the lounge when someone got bold.

Because let’s be clear: you never let a bitch play with you — not today, not during Pride, not ever.

So plug in, pour up, and prepare to feel seen, hear...

Listen… summer is coming, and it’s already way too hot for me to be out here in this car. I’m too grown to be sweating through my clothes before I even get where I’m going. In this episode, I discuss why I need a new ride as soon as possible and share my recent experience shopping for one. From dealing with pushy salespeople to figuring out what I want, it’s making grown-up decisions with a side of heat-induced attitude.

Don’t forge...

In this episode of Late Night with Sylvester, I’m gearing up for Memorial Day weekend and reflecting on the excitement around D.C.'s Black Gay Pride—one of my favorite times of the year. I also share my thoughts on switching barbers (yes, it's a big deal), and give you a quick recap of episode 2 of Baddies Africa—because the drama never sleeps, and neither do I. Tap in!

Don’t forget to subscribe, like, and give me my 10s i...

The Baddies Africa premiere is here, and I have thoughts — a lot of them. In this episode, I recap the season opener, dish on the cast, the drama, and who’s already standing out. If you love chaos, glam, and reality TV breakdowns, this one's for you. Let’s get into it!

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

X: @LNwithSylvester

Email: LateNightwithSylvester@gmail.com

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In this episode, I recap my recent trip to Houston — the vibes were high, the food was on point, and I definitely had a time. I also get into some real talk about money: how I decide what’s worth spending on, what I absolutely won’t drop a dime on, and why being intentional with my coins matters more than ever. Tap in for the stories, the laughs, and a little budgeting wisdom.

Don’t forget to subscribe, Like, and give me my 10s in t...

In this episode of Late Night with Sylvester, I recap my weekend before heading to Houston, starting with a surprise “brunch” that turned into a full-blown party at Joe’s. I also share the satisfaction of cleaning my apartment and tackling laundry (adulting, anyone?). But the real conversation kicks in when I ask: Do we still look down on sex work in 2025? Is it still taboo? And the big question—could I date a sex worker? I’m not s...

Babyyyy, I don’t know what’s in the air, but the men this week? TRIED it. In this episode, I break down a wild (and lowkey hilarious) hookup situation that had me like, “Oh, this what we doin’ now?!” From weird energy to straight-up foolishness, I had to gather my thoughts and my edges.

But don’t worry—I balance the chaos with some heart. I spent a few days housesitting with my little brother, and honestly, that boy has my whole hea...