Expensive Desperation | Black Gay & Lonely AF!
- J.R. Whittington
- 2 hours ago
- 7 min read

Black Gay & Lonely AF | "Expensive Desperation"
At night, I journal. In the morning, I try to catch the thoughts before they harden. This series comes straight from that place—old-school diary entries pulled from my dating life. Messy. Tender. Honest. It's not as polished as my other work, but it's unapologetic, vulnerable, and true. And that felt important to let live on the page.
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.
The brown liquid sat staring at me. I swirled it around. Then chugged it like a shot. It burned. But the burn? That's just my soul catching up to my throat.
Whiskey. I don't drink whiskey. Brown makes me dance on tables, start fights, text apologies I don't mean. I stick to vodka—clear, controlled, just a buzz. Clean like morning light through a window you forgot to close. But tonight? Brown won.
Because tonight required something stronger than my usual measured pour. Tonight required the kind of courage that burns going down and keeps burning long after.
I met a friend earlier. He sat across from me glowing like he'd swallowed something holy, talking about all these dates. Real dates. Dinner dates where the conversation stretched past dessert and into the kind of future-talk that makes you believe in possibilities. Second dates where neither of you is looking for an exit. Dates that lead somewhere other than a blocked number and another story I tell at brunch to make people laugh instead of pity me.
I smiled. Nodded. Said all the right things while something ugly twisted in my chest.
Envy. Sharp and specific. The kind that makes you hate yourself for feeling it while you're feeling it. Because he deserves this. And I want it. And somehow those two truths can't exist in the same room without one of them drawing blood.
I'm putting myself out there—or so I tell myself every time I open an app and pretend tonight will be different. That this profile won't ghost. That this conversation won't die after three messages. That someone will see past my photos and want to know the man holding the phone.
But the apps are a carousel that never stops. Same faces. Same lies. Same promises of connection from men who can't even commit to showing their actual face in their profile picture. Everyone performing availability while remaining completely unavailable.
Then he says it. Casual. Like he didn't just crack open a door I've been pretending doesn't exist.
"I'm seeing a matchmaker."
I choked. Actually choked on my iced coffee. Had to put the cup down before I died right there in the café, cause of death: shock that we've come to this.
"A matchmaker? Like Patti Stanger realness?"
He nodded. Unbothered. At peace with a decision I'm still trying to wrap my mind around.
Chyle, paying someone to find you love? That's surrender. That's waving a white flag embroidered with all your failures—every unanswered message, every ghost, every man who looked at you like a possibility and then changed his mind.
That's a billboard that says "I TRIED AND FAILED" in letters tall enough to see from across the city.
Desperation looks different when you're maturing. When you're past the age where loneliness is supposed to be temporary, a phase you grow out of once you get your life together. It doesn't scream. It doesn't beg on apps with thirst traps and captions about being unbothered.
It pays a monthly fee and calls it self-care. Calls it an investment. Calls it anything other than what it is: giving up on finding love the way love is supposed to happen and outsourcing your hope to a professional.
He slides the card across the table like contraband. Business card. Cream-colored. Expensive-looking.
"Tell him I sent you. Broke actor discount."
I called him a bitch. In the kindest way. The way you do when someone offers you exactly what you need but didn't want to admit you needed.
But I took the card.
Held it between my fingers like a lottery ticket. Like a last resort. Like hope wearing a price tag.
Now I'm home. Pouring another glass of brown. Watching it catch the light—amber and warm and deceptive. The color of things that hurt you slowly, sweetly, until you forget what it felt like not to burn.
And I hit send.
Typed out the email to a stranger who makes a living off loneliness. Referenced my friend. Tried to sound normal instead of desperate. Tried to sound like a man inquiring about services and not a man at the end of his rope typing please help me I don't know how to do this anymore.
Days pass like held breath.
Then he calls.
Cut to: me on Zoom, dressed like I'm interviewing for a job I desperately need. Shirt pressed. Hair right. Smile practiced. The job is love. The salary is hope. The benefits package includes someone to wake up next to and proof that I'm not meant to do this alone forever.
I tell him everything. Every failed relationship that taught me what I don't want. Every ghosting that made me question what I am. Every man who disappeared after promising he wouldn't. The pattern repeating itself so many times it stopped feeling like bad luck and started feeling like fate.
"I know you're a broke actor—"
Excuse me?
Broke actor. He really just said that. Like my bank account is part of the intake form. Like my tax bracket determines my capacity to love or be loved. Like being an artist who chose passion over profit makes me less deserving of—
"—but you deserve love too."
Oh.
And just like that, the sting softens. Not disappears. Softens. Because he's right and he's wrong and he doesn't even know it. Right that I deserve it. Wrong that broke has anything to do with it.
"These gay men in New York are brutal."
NOW we're talking.
Amen.
AMEN.
Finally someone saying out loud what I've been living. That it's not just me. That the city is hard. The scene is harsh. That the men here treat dating like a competitive sport where second place means you're nobody. Where one wrong answer, one awkward pause, one moment of not being perfect enough means you're deleted from their phone before you even make it home.
Brutal doesn't even cover it.
"You're a top. My database is filled with bottoms."
Chyle.
I'm a commodity now. Supply and demand. Market value determined by sexual position. And it should feel dehumanizing but instead it feels like validation—proof that I'm wanted, even if the want is transactional.
He tells me the price.
I laugh. Not a polite laugh. A desperate one. The kind that says "you think I have that kind of money? You already called me broke, remember?"
"I can't afford that."
Another number. Lower but still high. Still choosing between hope and groceries, between investing in a future and surviving the present.
Then a discount. The kind where you eat ramen for a month and cancel subscriptions and wonder if love is supposed to cost this much. If wanting someone is supposed to bankrupt you before you even meet them.
I'm about to pay a stranger to do what I used to do in my sleep—make a man notice me. Make a man want me. Make a man stay.
The rules are simple, which somehow makes them worse:
Text with a bio. No picture. Blind. Just words describing someone who might save you or ruin you.
If you both say yes, twenty-four hours to set up a date.
Love Is Blind, but expensive and gay. Reality TV played out in real time with your actual heart as collateral.
I am gagged.
Boo, I signed up.
Gave him my information. My preferences. My dealbreakers. Let him reduce me to bullet points on an intake form. Let myself become one more lonely man willing to pay for the possibility of not being lonely anymore.
You have to go the way your blood beats. That's what the old folks say. Follow your heart even when your head is screaming that you're making a mistake.
My blood's been beating alone so long I forgot what harmony sounds like. Forgot what it feels like to sync up with someone else's rhythm instead of keeping time by myself in the dark.
Maybe that's the whiskey talking. The burn in my throat that feels like courage but might just be desperation wearing a mask.
The matchmaker isn't hope. Let's be real about that.
It's a Hail Mary. Last play, fourth quarter, down by twenty with no timeouts left. It's the move you make when you've tried everything else and come up empty. When the apps have failed you, the bars have failed you, your own efforts have resulted in nothing but stories and an emptiness you can't joke away.
But it's a play. And I'm still in the game.
That has to count for something.
You can't will someone into existence. I know that. Tried it already. Manifested and visualized and put it out to the universe until the universe started screening my calls.
But you can stop pretending you don't need them.
You can stop calling loneliness a choice when it's really just what happens when every attempt to connect fails. When every man you want doesn't want you back. When every promising start ends the same way—with silence.
I pour one more glass. Amber. Warm. Deceptive.
The brown liquid doesn't judge me for what I just did. Doesn't remind me that people used to fall in love without algorithms and intake forms and strangers charging fees to introduce you. Doesn't lecture me about self-love, as if loving yourself makes you any less hungry for someone else to love you back.
It just burns. Clean and honest.
I stare at my phone. Waiting for a text that might save me. Or ruin me.


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