Hopeful Dread | Black Gay & Lonely AF!
- J.R. Whittington
- Mar 1
- 6 min read

This is my Black, queer Sex and the City—Black don't crack, love still dangerous, desire loud, standards high, heart open, and me refusing to shrink for anybody's comfort.
This that old-school diary vibe — scribbles-in-the-margins, headphones blasting, secrets that make me naked between each line.
Missed an essay — these stories flow chronologically, but each one can shine solo. Peep what came before? Just adds a little extra spice.
Matchmaker, matchmaker, make me a match. Find me a find, catch me a catch.
The song won't leave my head. I hum it at my window in Washington Heights, staring at the city like it owes me an answer. I'm not Jewish, but I love Fiddler on the Roof. Something about tradition—the rituals, the candles, the certainty that someone will show up because it's written, promised, arranged.
I'm living my Black Fiddler on the Roof fantasy, waiting for my match like Tevye's daughters waited for theirs.
Except nothing happens.
Days bleed into weeks. The silence gets louder, heavier, like a house guest who won't leave. Every morning I check my phone expecting the text that will change everything. Every night I go to bed with the same phone, the same silence, the same creeping suspicion that maybe I'm not matchable.
He said being a top was an advantage. Supply and demand, remember? But what if I'm too much of other things that cancel out the advantage? What if my expiration date already passed and nobody told me? What if the database is full of men looking for someone younger, simpler, less complicated than a loud Black gay actor-writer with opinions and a blog?
The thoughts circle like vultures over roadkill—patient, persistent, feeding on my hope until there's nothing left but bones.
I'm an actor. A writer. An artist. My entire life is waiting. Waiting for the callback that never comes. Waiting for the review that might destroy me or validate me or both. Waiting for someone to say yes when everyone's been saying maybe, not now, we'll be in touch.
Now I have to wait for a matchmaker I paid too much to find me what I used to find in my sleep.
Do they even have people of color in their database? The question sits in my throat like something I'm not supposed to swallow but can't spit out either. Because lately I've been craving Middle Eastern men—rich brown skin, thick beards, that effortless masculinity that makes my knees weak. They give cake. They give face. Eyes that hold centuries of stories I want to crawl inside and live in.
But I've never actually dated one.
Maybe it'll be a beautiful chocolate brother with emotional intelligence instead. Someone who gets the weight of being Black and gay in New York without me having to explain it. Someone whose skin matches mine, whose history runs parallel, whose survival looks like mine.
Maybe the universe will surprise me.
Maybe the universe forgot I'm here.
The waiting becomes its own kind of work. Checking my phone becomes a ritual—morning coffee, phone check. Lunch break, phone check. Before bed, after midnight, three AM when sleep won't come and loneliness sits on my chest like a lover I never invited but can't kick out.
Nothing.
I start imagining worst-case scenarios. What if the matchmaker took my money and forgot about me? What if there's a glitch in the system and my profile is sitting in digital purgatory, unseen, unchosen, gathering dust like a headshot from an audition I bombed?
What if I'm unmatchable?
Then my phone vibrates.
A text. An email. A bio.
My hands shake opening it. Actual tremors, like my body knows this moment matters more than I want to admit.
Biracial. Management. Warm. Thoughtful. Loves food, theater, meaningful conversation.
They sold this man like he was handcrafted just for me. Custom-built in some factory where they make partners for difficult people who want too much and settle for too little and can't figure out why they're still alone.
I read it once. Twice. Three times, searching for the red flag, the dealbreaker, the detail that'll let me dismiss him before I get my hopes up. Before I start imagining futures with a man I haven't met. Before I do what I always do—build a relationship in my head that reality can't possibly live up to.
Nothing. He's perfect on paper.
And that terrifies me.
Because paper doesn't talk back. Paper doesn't have bad breath or annoying laughs or opinions about things that matter to me. Paper is a placeholder for possibility, and possibility has burned me more times than I can count.
My heart starts drumming a rhythm I haven't felt in years—part excitement, part terror. Like standing backstage before your entrance knowing you only get one shot to not fuck this up. Like opening night when the critics are watching and your career depends on not forgetting your lines.
But first, I have to say yes. And so does he.
The matchmaker's rules are clear: We both get profiles with no pictures. We both have to agree. We have twenty-four hours to decide if we're willing to gamble on a blind date with a stranger who might be everything or nothing.
What do I wear? The question hits me before I even accept, before I know if he'll accept, before anything is real. But my brain is already three steps ahead, picking outfits, imagining entrances.
I love clothes. Fashion is armor. Do I show cleavage? Do I let the pecs breathe? Should I give butch queen realness or serve full femininity? Do I walk in like I already won or like I'm auditioning for the part of someone worthy of love?
Stop. Breathe.
You have to say yes first.
I call my friend. The same one who gave me the matchmaker's card. The same one who's been glowing with new relationship energy while I've been drowning in expensive desperation.
"Just say yes," he tells me. "What's the worst that could happen?"
Everything, I think. The worst that could happen is everything I want and nothing I can keep. The worst is hope followed by disappointment. The worst is meeting someone wonderful and finding out I'm not wonderful enough for them. The worst is discovering that even professional help can't fix what's broken in me.
But I hit accept anyway.
Because hope is a drug and I'm an addict. Because loneliness makes you brave in ways that have nothing to do with courage and everything to do with desperation. Because I paid too much not to see this through.
Hours pass. I check my phone like it's a slot machine about to pay out. Like if I stare hard enough, I can will the notification into existence.
Then it comes: He said yes too.
And just like that, possibility becomes real.
We text. Polite. Careful. Feeling each other out through punctuation and emoji choices like we're doing some delicate negotiation where one wrong move could blow the whole thing.
We decide on lunch. Hell's Kitchen. Neutral territory. Meeting in the middle like two countries signing a treaty, both hoping for peace but preparing for war.
The days between yes and the actual date stretch like taffy. I change my outfit seventeen times. Practice my entrance. Rehearse casual greetings in the mirror like I'm preparing for a role where the character is someone people want to date.
I decide on studious-but-sexy—button-down open just enough to show the chest I work too hard on at the gym. Sex sells in my industry, so why not sell it a little on a date? Why not use every tool I have?
The day arrives and I'm ready. Or at least I look ready.
I arrive early because actors are always early, trained by years of auditions to never keep anyone waiting. Never give them a reason to remember you for the wrong thing.
I watch the door like a hawk stalking prey.
Every time someone walks in who looks remotely biracial, my head snaps so fast I might pull something. What is he mixed with? Black and White? Middle Eastern and Black? Latino and Asian? The combinations shuffle through my mind like a dealer laying out cards I can't read yet.
My palms sweat. My heart races. This is it. This is the moment where hope either dies or survives to disappoint me another day.
Then the door opens.
He walks toward my table. Confident. Unhurried. Present in a way that makes everyone else in the restaurant fade into background noise.
The first thing I notice is— TO BE CONTINUED


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