The Algorithm Knows I’m Single

My phone knows I’m single before I do.

It’s Tuesday. I’m at Gregory’s on Park Ave. The line’s seven people deep. Everyone’s on their phones.

I’m on mine too.

Emma, 31, liked my photo. I don’t know Emma. The app says we’re 87% compatible.

The app doesn’t know I still listen to The Strokes unironically. That I haven’t updated my LinkedIn in three years. That I’m thirty-seven and still don’t own a couch that wasn’t delivered in a box.

The barista’s waiting. Oat or almond. I can’t decide. In New York, your coffee order says something about you. Mine probably says I peaked in 2014.

I met Sarah last week. Meatpacking. Brand strategist. Whatever that means.

She wore this Balenciaga t-shirt that probably cost more than my Con Ed bill. The cocktails were $19. She ordered something with mezcal and thyme.

“I’m consciously uncoupling from capitalism,” she said.

I nodded. I didn’t mention the $19 cocktail.

You don’t mention things like that. Not on first dates. Not when you’re trying to seem like you have your shit together. Which I don’t. Nobody does. We’re all just faking it with better lighting.

She told me about her podcast. About manifesting. About her apartment hunt. Almost three grand for a studio with a window that faces a brick wall.

She said it had “character.” Character costs extra in Manhattan. So does exposed brick. So does everything. So does pretending you’re happy about it.

I told her about my work. Graphic design. Freelance. Which is code for “some months are good, some months I eat bodega sandwiches for dinner.”

She seemed impressed anyway. Or maybe just polite. New Yorkers are very good at being polite when they’re not interested.

We talked for two hours. She was smart. Funny. Pretty. The kind of pretty that makes you sit up straighter.

She knew about art. Real art. Not the stuff people pretend to like on Instagram. She’d been to Berlin twice. I’ve been to Jersey City. Not the same thing, apparently.

Around eleven, we left. Some guy in an Elmo costume was screaming at a cab driver. Welcome to New York. The greatest city in the world, if you ignore all the evidence to the contrary.

Sarah laughed. I liked her laugh. It was real. Unselfconscious. Rare.

“Text me,” she said.

I haven’t texted. She hasn’t either. We’re both waiting. That’s the game now. First person to reach out twice loses.

I don’t remember when dating became a strategy game.

Probably around the same time everyone stopped calling and started “circling back.” I hate that phrase. Circle back. Like we’re all just corporate drones in our personal lives now, too.

Marcus says I overthink everything. Marcus works in finance. He dates like he trades. Multiple positions. Low emotional investment. Stop-loss orders on feelings.

He’s forty-one. He says he’s “keeping his options open.” His options include a marketing director in Soho and a yoga instructor from Park Slope who’s never heard of The Sopranos.

“Just text her,” he said over drinks Friday.

“I will.”

“When?”

“Soon.”

He rolled his eyes. Marcus is always rolling his eyes at me.

We’ve known each other since college. He still brings up the time I dated a girl for about a year without defining the relationship. That was twelve years ago. He’ll never let it go.

That’s what friends are for. Holding your past against you.

Here’s the thing. I think I like her. Sarah. She probably likes me too. We laughed at the same stupid jokes. She touched my arm twice.

But we’re both so goddamn careful now. Like if we admit we want something, it’ll disappear. Poof. Gone.

Like rent-controlled apartments and dive bars that haven’t been turned into luxury condos. Which is all of them now.

When did we get so afraid?

I used to call girls I liked. Just pick up the phone and call.

Now I’m drafting text messages in my Notes app like they’re work emails. Subject line: potential romantic interest. Body: casual but not too casual. Emoji or no emoji? It’s exhausting.

The coffee’s ready. I paid with my phone. Everything’s on my phone. My money. My dates. My entire life, really.

Sometimes I think about what it was like before. Before the apps. Before everyone became their own PR agency. It wasn’t better, exactly. But it was simpler. You met someone. You asked them out.

They said yes or no. Now there’s thirty steps in between, and nobody knows what any of them mean.

I’m walking back to my apartment. Not an office. I work from home. Which sounds great until you realize you haven’t spoken to another human before noon in three days.

My couch was delivered in three boxes. I assembled it myself. One of the legs is slightly uneven. I think about this every time I sit down. Which is often.

My phone buzzes. Sarah posted a story. She’s at some gallery opening in Chelsea. She looks happy. She’s with friends. I recognize one from her photos.

The tall one who always looks vaguely disapproving. Everyone in New York has a friend who looks vaguely disapproving. It’s part of the ecosystem.

I could text her. I want to text her. That’s the embarrassing truth. I actually want to see her again. Want to know if she laughs at my jokes sober.

Want to know what her apartment looks like. If she’s a morning person. What she orders at diners at 2 AM. If she even goes to diners at 2 AM. Maybe that’s not a thing anymore either.

But I’ll wait. Maybe until tonight. Maybe tomorrow.

Give it the regulation forty-eight hours so I don’t seem desperate. Even though I kind of am.

Desperate for connection. For something real. For someone who doesn’t make me feel like I’m performing my own life for an audience of nobody.

That’s New York for you. City of eight million people. You can walk down Fifth Avenue at rush hour, surrounded by bodies, and feel completely alone.

Everyone’s looking. Everyone’s lonely. We’re all just too proud to admit it first. Too sophisticated. Too cool. Too something.

My phone buzzes. A work email. A client wants revisions. Always revisions. Nobody’s ever happy with the first version. Or the second. Or the third. I’ll deal with it later. Which means tonight at 11 PM when I can’t sleep.

I think about Sarah’s laugh again. About her hand on my arm. About the way she said “text me” like she meant it. Maybe she did. Maybe she didn’t. Maybe it doesn’t matter.

Maybe the algorithm doesn’t know what I want.

But I’m starting to.

D.S.

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—”The Unmarried Man” is a weekly column about dating and life in New York City through the eyes of a thirty-something man navigating modern romance.