The Rush: When Comfortable Feels Terrifying

Sarah and I have been seeing each other for three weeks.

That’s what we call it. “Seeing each other.” Not dating. Not exclusive. Just… seeing. It’s vague enough to mean everything and nothing. Very convenient. Very modern. Very cowardly.

We’ve been out five times. Maybe six if you count the afternoon coffee at Ludlow Coffee Supply that turned into drinks at Attaboy. Which I do. She doesn’t.

We haven’t agreed on the rules yet. We probably never will.

Tuesday night, we ended up at her place in Alphabet City. Third-floor walk-up. No elevator. My knees reminded me I’m thirty-seven.

Exposed brick. String lights. A bookshelf organized by color, which should’ve been a red flag but wasn’t.

She poured wine. Trader Joe’s. Eight dollars a bottle. Tasted like twelve. We sat on her couch that definitely came in fewer boxes than mine.

“So what are we doing here?” she asked.

“Drinking wine that costs less than our therapy sessions.”

“You know what I mean.”

I did. I’d been avoiding the question for three weeks. We both had.

Avoidance is a love language in New York. Right up there with passive aggression and saying you’re five minutes away when you haven’t left yet.

The thing is, we work. On paper, we absolutely work. She’s smart. Funny. Gets my references. Laughs at my jokes even when they’re not that good.

The sex is good. Not earth-shattering, but solid. Consistent. Better than most. We have chemistry. Real chemistry. The kind you’re supposed to want. The kind that’s supposed to be enough.

“I like you,” I said.

“I like you too.”

“But?”

She smiled. Took a sip of wine. “No but. I do like you. That’s the problem.”

I understood exactly what she meant. That was the other problem. We understood each other too well. It’s easier when you don’t.

We spent the night together. Woke up on Wednesday morning. She made coffee. Good coffee. French press. The whole routine.

Apparently, she’s one of those people who actually uses kitchen appliances instead of just storing them.

We sat at her kitchen table—actual table, actual chairs, very adult—and talked about nothing important. Work. The subway. Whether the bagel place on Avenue A is actually good or just convenient.

Spoiler: It’s just convenient. Everything in New York is just convenient until you realize you’re paying eighteen dollars for mediocrity with better marketing.

It felt nice. Easy. Comfortable.

I hated it.

Not in a bad way. In a “this is what I’m supposed to want” way. In a “why doesn’t this feel like enough” way. In a “my therapist would have a field day with this” way.

She walked me to the door around ten. Kissed me. Said “text me later.”

I texted her later. We made plans for Friday. Dinner at Westville. Another nice, easy night. Another step toward whatever this was becoming. Or not becoming. Hard to tell.

Marcus called Thursday.

“How’s Sarah?” he asked.

“Good. Great, actually.”

“So why do you sound like someone died?”

“Nobody died.”

“Then what’s wrong?”

“Nothing’s wrong. That’s the problem.”

He laughed. “You’re an idiot.”

Maybe. Probably. Definitely.

But he didn’t get it. When things work, when they’re easy and comfortable and nice, that’s when the panic sets in.

That’s when you realize the excitement wasn’t in having someone. It was in trying to get them.

The chase. The uncertainty. The three-day wait before texting. The wondering if she’ll text back. The dopamine hit of a notification.

We’re all just rats in a very expensive, very stylish Skinner box.

Friday came. We met at Westville. She looked good. She always looks good. That’s not the issue. The issue is I looked at her and felt… fine.

Just fine. Not excited. Not nervous. Not anything particularly strong. Just pleasant. Comfortable. Safe.

Terrifying.

We ordered. We talked. We laughed. All the things you’re supposed to do on a date with someone you like. Someone you’re supposed to be falling for.

But falling requires momentum. This felt more like floating. Or sinking. Hard to tell the difference.

Halfway through dinner, my phone buzzed. Dating app notification. Someone liked my photo. I should’ve deleted the apps. I told myself I would. I hadn’t.

Neither had she. I could tell by the way she glanced at her phone when she thought I wasn’t looking.

We’re all terrible liars. Especially to ourselves.

“Can I ask you something?” she said.

“Sure.”

“Are you still… you know.”

“Swiping?”

“Yeah.”

I could’ve lied. Should’ve lied. Would’ve been easier. “Sometimes.”

She nodded. Didn’t look surprised. Didn’t look hurt. Just nodded like I’d confirmed something she already knew. “Me too.”

We sat there for a minute. Not awkward. Just honest. Uncomfortably honest. The kind of honesty that makes you realize you’re both doing the same shitty thing for the same shitty reasons.

“What’s wrong with us?” I asked.

“Nothing. Everything. I don’t know. Probably capitalism.”

I laughed. She did too. See? We work. We get each other. We’re perfect together. Except we’re not.

“We like each other,” I said.

“We do.”

“The sex is good.”

“It is.”

“We laugh at the same things.”

“We do.”

“But?”

She put down her wine glass. Looked at me. Really looked at me.

“But we’re not… I don’t know. We’re not it for each other. Are we?”

She was right. We both knew it. We’d probably known it since the first kiss.

Maybe before. Maybe the second she said “text me” and I calculated the optimal wait time instead of just texting her when I wanted to.

The thing about modern dating is that nobody talks about this part. They talk about finding the one. About chemistry and compatibility and all that bullshit people say in wedding toasts.

They don’t talk about what happens when you find someone good and realize good isn’t enough. When you realize you’re more excited about the notification on your phone than the person sitting across from you.

When you understand that somewhere along the way, we all got addicted to the search more than the finding.

We’re hunter-gatherers in a world where everything’s already been gathered. So we just keep hunting. For what? No idea. But the hunting feels better than the having.

We finished dinner. Split the check. Very equitable. Very modern. Very “we’re not really together anyway.”

Walked toward the subway. Stopped at the corner of 7th and Avenue A. Same corner where I kissed her three weeks ago. Full circle. Or maybe just a circle with no exit.

“So what now?” she asked.

“I don’t know. Friends?”

“Friends who occasionally sleep together?”

“Is that a thing?”

“In New York? Everything’s a thing. We’ve got situationships, soft launches, breadcrumbing, benching. We’ve invented fifty words for not committing.”

She was right. Everything is a thing here. Friends with benefits. Casual dating. Seeing each other. Hanging out. Talking. We’ve created an entire vocabulary to avoid saying “relationship” or “nothing.”

Gray area is the new black.

“I like you,” I said again.

“I like you too. That’s why this might actually work.”

We kissed. Not like the first time. More like goodbye, but not really goodbye. Like, see you later, but maybe not romantically.

Like, thanks for being honest, even though honesty kind of sucks, and now we both have to go home and feel weird about it.

She took the L train. I took a cab. Expensive. Unnecessary. But I didn’t want to see people. Didn’t want to sit next to someone reading a book and remember when that used to seem profound.

Texted her when I got home.

“Tonight was good.”

“It was. Talk tomorrow?”

“Yeah.”

I poured bourbon. Sat on my couch. Still uneven. Still mocking me.

Opened the dating app I should’ve deleted weeks ago. The one I promised myself I’d delete after meeting Sarah. The one I definitely should delete now.

Swiped for twenty minutes. Felt nothing. Felt everything. Felt like a fucking cliché. Like every man in every city doing the exact same thing at the exact same time. A symphony of loneliness and bad decisions.

Marcus is right. I’m an idiot.

But so is everyone else in this city. We’re all idiots together. Eight million people looking for something we can’t define. Running from things that might actually make us happy.

Convinced the next swipe will be different. The next person will be it. The next date won’t feel like we’re going through motions we learned from too many failed attempts.

Maybe Sarah and I will work as friends. Maybe we’ll hook up occasionally when we’re both between better options.

Maybe we’ll both find what we’re looking for somewhere else. On some app. At some bar. In some coffee shop where the line’s too long and the barista knows our order.

Or maybe we’re all just fucked. Maybe we’ve gamified dating so hard we forgot how to actually want someone.

Maybe the apps broke something fundamental in us. Maybe we’re the first generation to have everything and feel empty about it.

At least the bourbon’s good. At least the couch is familiar. At least I’m honest about how dishonest we’ve all become.

That’s something.

Not much. But something.

More than most people can say.

—D.S.

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“The Unmarried Man” is a weekly column about dating and life in New York City from the perspective of a man in his late thirties.