The Text (Or: How I Learned to Stop Worrying and Just Hit Send)

I texted Sarah on Thursday.

Three days after the date. Not two. Not four. Three felt right. Or maybe it just felt less wrong. Like ordering the second-cheapest wine on the menu.

“Hey. That was fun the other night. Want to do it again?”

I stared at it for ten minutes before hitting send. Deleted the period after “Hey” because periods make you look angry now. According to someone’s think piece I read at 2 AM. Added it back. Deleted it again.

This is what we’ve become. Grown men analyzing punctuation like it’s the freaking Rosetta Stone.

She responded in seven minutes. I know because I counted.

“Yes! When?”

Exclamation point. That’s good, right? Or is it performance? Everyone’s performing now. We’re all just Broadway shows with an audience of one who might be scrolling Instagram during Act Two.

We made plans for Saturday. Death & Co in the East Village. Somewhere dark with good whiskey and no DJ playing house music at volumes designed to prevent human conversation. Because why would anyone come to a bar to talk?

Marcus called Friday night.

“You’re overthinking it,” he said.

“I’m not.”

“You absolutely are.”

He was at Westlight in Williamsburg with the yoga instructor. I could hear music in the background. Laughter. The sound of people having a good time without questioning every goddamn thing about it.

That’s the difference between Marcus and me. He’s enjoying the ride. I’m wondering who’s driving, where we’re going, whether we have enough gas, and whether the driver has good reviews.

“Just show up. Be yourself. Stop making it complicated.”

Be yourself. The most useless advice ever given. Right up there with “follow your dreams” and “it is what it is.”

Which self? The one who reads books nobody’s heard of so he can feel superior at parties he doesn’t want to attend?

The one who pretends he doesn’t care about money while secretly checking his bank account three times a day, as it might spontaneously improve?

The one who’s slept with enough women to know the difference between wanting someone and wanting not to eat cereal alone at midnight?

I met Sarah at nine. She was already there. Sitting at the bar in a leather jacket. Hair down. The kind of effortlessness that takes an hour and costs a fortune in products with names like “texturizing mist.”

She looked good. Better than I remembered. Or maybe I just forgot how to remember things accurately. My brain’s been on the internet too long.

“You’re late,” she said.

“Traffic.”

“You took the subway.”

“Subway traffic. Very real. Very traumatic. There’s probably a support group. Meets Thursdays in Tribeca. Costs forty-five dollars a session.”

She laughed. Real laugh. Not the polite kind you give when your date makes a joke that lands like a dead pigeon.

I sat down. Ordered bourbon. She had wine. Red. The bartender knew her. Called her by name. In New York, your bartender knows more about you than most people you’re sleeping with.

We talked. Really talked. Not the first-date performance where you list your hobbies like you’re interviewing for a job you’re not qualified for. “I love hiking.” You went once. In 2019. You hated every minute.

About work. She’s between projects. Which is freelance for “between paychecks.” I know that dance.

The freelance waltz.

One month, you’re booking Ubers without checking the fare. Next month, you’re doing mental math on whether you can afford guacamole. Extra guac? Let’s not get crazy. You’re not a Rockefeller.

About family. Her mother calls every Sunday. Wants to know when she’s moving back to Ohio. Wants grandchildren. Wants her daughter to stop wasting her thirties in a city that doesn’t care if she lives or dies.

Her mother’s not wrong. New York doesn’t care. It really doesn’t.

That’s not a metaphor.

The city actually doesn’t give a shit. That’s the point. That’s why we stay. We’re all just seeking validation from something that will never, ever give it to us. Very healthy. Therapists love it.

“My sister lives in Portland,” she said. “She keeps telling me to move out there. Says I’d be happier.”

“Would you?”

“Probably not. I like being miserable here more than I’d like being content somewhere else.”

I understood that perfectly. Everyone who stays in New York understands that. We’re masochists with good taste.

We pay thousands of dollars a month to live in shoeboxes and call it character. We wait forty minutes for brunch at Clinton St. Baking Company like we’re waiting for an audience with the Pope.

We’re subway rats in designer jeans, convincing ourselves the struggle means something. It probably doesn’t. But at least we’re struggling with style. And decent coffee. The coffee here really is better.

Around eleven, the bar got crowded. Bridge and tunnel crowd.

You can always tell.

The guys wear too much cologne. Enough to make your eyes water. The women wear heels they can’t walk in and will complain about on social media for the next three days.

They come to Manhattan like it’s Disneyland for adults who make poor financial decisions. Which it is. Except the rides are broken. The staff is rude. And you pay more than twenty dollars for a drink that tastes like regret with a hint of lime and someone’s bad life choices.

“Want to get out of here?” I asked.

“Thought you’d never ask.”

We walked toward Tompkins Square Park. The streets were full. Friday night in the East Village.

NYU kids stumbling out of Phebe’s.

Homeless guys asking for change from people who just paid twenty-two dollars for a cocktail they can’t pronounce. Mezcal. Activated charcoal. Small batch bitters. Because regular drinks aren’t artisanal enough.

A woman walking three dogs that probably have better healthcare than most Americans. Welcome to late-stage capitalism with good restaurants and impossible rent.

“You ever think about leaving?” she asked.

“Every day.”

“But you don’t leave.”

“No.”

“Why not?”

“Because everywhere else is worse in less interesting ways. At least here the misery is expensive and well-documented on Instagram.”

She smiled at that. She gets it. That’s the thing about Sarah. She’s not impressed by the city.

She’s not one of those people who moved here to “make it” and posts skyline pictures from The High Line like they discovered Manhattan. Like Columbus, but with worse navigation skills and student debt.

She knows New York is a beautiful disaster.

An expensive mistake we keep making. A toxic relationship we refuse to leave because we’ve already invested so much time and money. Sunk cost fallacy with better bagels.

We stopped at the corner of Avenue A and 7th Street. She looked at me. I looked at her. This was the moment. Kiss her or don’t. Make a move or play it safe. I’ve played it safe my whole life. Where’s it gotten me?

Alone on Friday nights, overthinking everything, wondering when I became the kind of man who needs a committee meeting and a cost-benefit analysis to decide if he should kiss someone.

I kissed her.

Not because I planned it. Not because I read some article titled “7 Signs She Wants You To Kiss Her” written by someone who’s never kissed anyone outside a focus group.

Just because standing there, on that corner, with her looking at me like maybe I wasn’t as disappointing as most men she’d met on apps. It felt like the only honest thing to do.

She kissed me back. Good kiss. The kind that makes you forget you’re standing on a dirty street corner in Manhattan while some guy fifty feet away yells about chemtrails and the lizard people running Citibank.

When we pulled away, she smiled. “You took long enough.”

“I was being respectful.”

“Bullshit. You were being scared.”

She was right. I was scared. Of liking her too much. Of not liking her enough. Of ruining it before it has a chance to ruin me.

Of being vulnerable in a city that punishes vulnerability like a parking ticket you forgot about until it doubles.

Of wanting something real in a place built entirely on transactions and Instagram captions and people pretending they’re happy.

“Maybe a little,” I said.

“That’s okay. Scared is honest. Better than whatever game most guys are playing.”

We stood there another minute. Neither of us ready to leave. Neither of us knowing what comes next. That’s the thing about New York. Nobody knows what comes next. We’re all just improvising.

Pretending we have five-year plans. Pretending we know where we’re going. We don’t. None of us do. We’re all just winging it with better vocabularies and worse mental health.

“I should go,” she said finally.

“Yeah.”

“Text me.”

“I will.”

“Not in three days.”

“Tomorrow. Maybe even tonight if I have something interesting to say. Which is unlikely but possible.”

“Good.”

She walked toward her apartment. I watched her go. Waited until she turned the corner.

Old habit. Making sure women get home safely. My mother raised me right. Even if nothing else stuck.

The 1st Avenue L train platform was empty. Just me and some guy playing guitar. Badly. Really badly. Like “just learned three chords this morning on YouTube”.

I gave him five bucks anyway. Friday night generosity. Or guilt for having a good night when most people don’t. Hard to tell the difference. They feel the same after bourbon.

My phone buzzed. Sarah.

“Made it home. That was fun. Let’s not wait so long next time.”

I texted back immediately. “Deal.”

The train came. I got on.

Sat next to a guy reading a book. A real book. Paper and everything. In 2025. Might as well have been using a sundial or sending telegrams. I wanted to shake his hand. Tell him he was keeping civilization alive, one page at a time.

But this is New York. You don’t talk to strangers unless they’re bleeding or on fire. Sometimes not even then. Mind your business. That’s the rule.

Went home. Poured bourbon. Sat on my uneven couch, still uneven, still annoying, still mocking me, and thought about her smile.

About how rare it is to meet someone who doesn’t make you feel like you’re wasting your time.

Sarah feels different. Or maybe that’s what I hope this time. Maybe hope is just another word for amnesia with better marketing. Who knows.

Either way, tonight was good. Real. Honest.

In New York, that’s enough. It has to be. Because nothing else is guaranteed. Not the rent staying the same. Not the subway running on time. Not the person you kissed on Friday still texting you on Monday.

But tonight? Tonight was good.

D.S.

---

—”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.