Late Night with Sylvester

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.

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

...

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.

—
 Don’t forget...

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

Intro Audio Zeus Network:...

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...

In this episode of Late Night with Sylvester, I’m getting ready to step out with friends—but first, let’s talk prep. Yes, that kind of prep. The bottom struggle is real, and I’m here to share the hilarious (and frustrating) truth. I also dive into my all-work weekend, staying committed to the gym grind and calling out the insecure men who pop up in my DMs and on the apps. Tap in for real talk, laughs, and a little shade—why not?

Lik...

In this episode of Late Night with Sylvester, I dive into my search for a new car—my third one—and share my experiences navigating the buying process. I also talk about working part-time on weekends to keep that steady cash flow.

On the deeper side, I discuss the 2025 Mandate for Leadership, touch on the Russia-Ukraine war, and break down why being associated with shady behavior just isn’t cute. It’s a mix of personal updates, real-...

In this episode of Late Night with Sylvester, I get into the latest episode of Baddies on the Zeus Network—because you know I have thoughts! Then, I switch it up and discuss why leaders need to keep learning and growing (because the title alone isn’t enough). With daylight saving time behind us, I’m hyped for spring and summer vibes! 🌞 Plus, I get into the art of "matching" when smoking—everyone does it differently, but ...

In this episode of Late Night with Sylvester, I am gagged and distraught after discovering that two guys I know know each other—and the tea doesn’t stop there. A video of me entered their conversation, and I have thoughts. 🤯 Why are men like this?! Let’s talk about boundaries, respect, and why this situation is weird.

Plus, it’s Black History Month, and while a lot is happening worldwide and in the U.S.A., we’re taking a moment to ...

In this episode of Late Night with Sylvester, I share my excitement about taking the show to YouTube Podcast and my big dreams for where it’s heading. 🎥✨ I also get real about using sex as a way to cope with tough times because we all have our ways of dealing with pain and hurt. Tune in for some deep thoughts, a little vulnerability, and a whole lot of ambition. 🔥

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

In this episode of Late Night with Sylvester, I reflect on the past few days of having a man in my place, which felt a little strange but still enjoyable. I also dive into a fun night out with friends where the vibes were right, the laughs were plenty, and yes, I was out here playing in faces (flirting, of course, 😉). On a more introspective note, I talk about going through a background check, navigating different jobs over the pa...