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.
Microsoft ☕
In this episode, I'm catching y'all up on my day and a few things that have been on my mind lately.
It's Movember, and I talk a little about what this month represents and why it makes me feel empowered. I also finally made it back to therapy after not going since August, and honestly, it was refreshing to be back in that space.
Of course, I had to talk about work because Microsoft had an outage, and let's just say productivity wasn't on the agenda that day! Sometimes there's only so much you can...
If You Saw Me, You Saw Me
Halloween has officially come and gone, and I'm back to tell y'all a little about my weekend!
I got into my Halloween festivities, and one thing about this year? I didn't take a single picture. So, if you saw me, you saw me! Sometimes you just have to enjoy yourself without documenting every moment.
As much as I enjoy being outside, I'm actually happy it's over because it's time to shift my focus back to work and getting things done.
It's another episode of me talking about life, enjoying the moment, and knowing...
Who's The Villain?
I'm back from Atlanta, and gurl, do I have some things to talk about!
This trip was a little different because I traveled to Atlanta for my grandfather's funeral. While it was sad, it was also a memorable experience being around family. And one thing I realized during this trip? My family needs its own reality TV show! The personalities, the dynamics, and everything in between deserve cameras.
Somehow, I missed my flight back home because I was too busy being nasty and bad! And before anybody says anything, I take full responsibility. It was...
My House, My Rules
In this episode, I'm recording while I edit my last episode of Late Night with Sylvester, and I have a few things on my mind.
For some reason, I've been feeling the urge to host something at my apartment. I love the idea of bringing people together, but there's just one problem: I don't like people being in my shit! So, of course, I had to talk about that little internal struggle.
On a more personal note, I also talk about the passing of my grandfather, preparing for everything that comes with saying goodbye, and...
Cleaning House
In this episode, I'm revisiting the situation with the guy I was dating, including the last time we saw each other when he came to visit me and how things ultimately ended with him ghosting me.
Sometimes it takes a little time before you're ready to unpack an experience, and I'm finally getting some of those thoughts off my chest.
On another note, I finally booked a professional cleaning service for my apartment! I'm getting into that experience and giving y'all another little update on what's happening in my world.
Don’t fo...
Weeks Like This…
I start this episode celebrating a really special milestone: my grandmother's 90th birthday. I talk a little about my family, our dynamic, and how I've gotten to a place where I'm comfortable with where I stand with my family and the relationships I have with them.
Meanwhile, this week wore me OUT. I was sick all week and still working through it, and it had me thinking about how weeks like this make me wish I had a man. Sometimes you just want somebody there when you're tired, sick, over it, and don't want to do everything...
Hey Jezebel
It’s been a minute, but I’m back! I start this episode by getting into the RHOA reunion and giving my shout-outs to some of the women on the show. And somehow, “Jezebel” enters the conversation—which leads to me talking to Siri throughout the episode to help me define words. Apparently, Siri has a role on the podcast now. 😂
I also talk about how excited I am for my upcoming vacation to Dallas and how ready I am to get away and enjoy myself.
I finally talk about what happened with the guy from DC I was...
Muva
Fresh off my trip to Puerto Vallarta, I'm back with a few things I need to get off my chest.
PVR was an amazing time and exactly the kind of Pride experience I needed. Somewhere along the way, I earned the title of "Muva"—and honestly, it might be sticking.
I also talk about the drama that unfolded during the birthday boy's cocktail hour. Some guests tried it, and I had to get a few people together. The funny part? They couldn't take me... and I genuinely did not care.
I al...
Pride Looks Good on Us
It's Pride Month, and in this episode, I'm talking about what Black Gay Pride looks like in our community and why I love it so much. From the joy and freedom to the connections and culture, there's something special about seeing us show up as our authentic selves and celebrate each other.
I also get into my personal shopping style and how I approach finding things that fit my personality, lifestyle, and taste. Because if you're going to be outside for Pride, you might as well look good doing it.
This episode is all about...
Being Intentional Ain't Cheap
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 upcoming trip to Puerto Vallarta. Between travel planning, dating, work, and everyday responsibilities, I'm trying to find b...
Fresh Pu**y
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 Wednesday, and what I’ve been noticing about...
Wendy Williams
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 something, I hit you with a track. So, hop in—this is the vibe we’re on tonight!<...
The Homie Can Get It Too
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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Can She Sit With Us? 🌴
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. Sometimes self-contr...
BIGO Live
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 staying in motion.
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Don’t forget to subscribe, like, and give me my 10s in the com...
Still A Barb
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 HIV prevention, and being responsible about your health is something I take seriously.
We Like It Raw
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.
This episode is about health, honesty, resp...
Can We Talk?
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 is about honesty, clarity, and facing what you feel instead of avoiding it.
It's Called "Customer Service, Sweetie"
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.
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X: @LNwithSylvester
Email: [email protected]
Intro Audio IG: @perfectprophet
Music: Summer Walker - Playing...
Cocktail Gurl in a Plastic Cup World 🍸
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.
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X: @LNwithSylvester
📧 Email: [email protected]
🎧 Intro A...
This Big Back Bit*h
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 it.
Despite the wild start, the trip was amazing overall. I had a great time, made memories, and stepped into the New...
Are You Wearing Red Tonight?
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 all, my best friend calls me out of the blue — and...
The Verse Agenda
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 to my first Black Market party, and from there, the night escalated, eventually landing me at the...
Ice, Hennessy, Lemonade & Cake
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 seasoning, knowing who they are… it just hits different.
It’s a mix of friendship, mess, nightlife, and grown-man appreciati...
The Red Door
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 you know I’m going to say them.
And la...
Bitch, You Saw Me
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 mom’s birthday party — surrounded by my Jamaican people, music bumpin...
I Been In The Mirror
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 the faint of heart.
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Does He Eat Butt?
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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Sweet Dreams
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 up being fat or ugly (no shade, just facts). It’s giving unfiltered, it’...
Nuts In My Mouth
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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X: @LNwithSylvester
📧 Email: LateNightwithSyl...
$500
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 memories made.
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Rest My Hole
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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I Want & Need My Man
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 wanting love and support doesn’t take away from your independence. Between new wheels and new i...
Been Done. Been Been.
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. Plus, I’m reminding you why it’s so important t...
Still Pride. Still Petty. Still Car-less.
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 always, Sylvester delivers it with heart, honesty, and humor.
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Don’t forget to subscribe, like, and give me my 10s in...
Who Is She Talking To?
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, heard, and ready to stand your ground.
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Don’t for...
Put Me In A Car
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.
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X...
Me & The Baddies
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!
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X: @LNwithSylvester
Email: [email protected]
Intro Au...
"Pretty Privilege": Baddies Africa Recap Ep.1
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!
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X: @LNwithSylvester
Email: [email protected]
Intro Audio Zeus Network: SERIES PREMIERE Baddies Africa: Before the Motherland
Music: NO GUIDANCE x WORK (by Baddie)<...
Living My Hood Fish Fantasy
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 the comments!
X: @LNwithSylvester
Email: [email protected]
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