Let me tell you—dating in NYC is actually awesome

Time Out

2 days ago

'Let Me Tell You' is a series of columns from our expert editors about NYC living, including the best things to do, where to eat and drink, what to see at the theater—and in today's edition why to stay optimistic about our city's dating scene.
At the very top of the list of claims I'm challenging—right up there with 'don't text him first'—is the idea that New York City is one of the worst places to find love.
I write this as a single, heterosexual, 34-year-old divorcée. No roster. No situationship. No crush. (Okay, maybe one. Two if I'm delusional.) Basically, no prospects. (At least not at the time of publication.)
And while you might already be rolling your eyes, waiting for the inevitable twist where this turns out to be a piece of ironic New Yorker -style satire, I'm not kidding. Take my hand. We're being earnest now.
Dating in New York is actually awesome. Not because it's easy. (It's not.) It's messy and chaotic and everyone is perpetually 15 minutes late to a first date and maybe still in love with their ex.
This isn't about being a hopeless romantic. It's about being open to the sheer chance of it all.
It's the fact that the simple act of ordering a martini, joining the run club or locking eyes on the subway can lead to a conversation, which can lead to a connection, which can turn into a crush, which can become a love story.
Yes, it sounds rom-com coded. Yes, I did watch Materialists twice in one weekend. (And I'd do it again.) But this isn't about being a hopeless romantic. It's about being open to the sheer chance of it all.
If you're reading this, I sense you're a nonbeliever. Your algorithm is likely filled with think pieces about the so-called 'romantic recession,' about how dating apps are broken, how 'boy sober' is trending, how the romance sections at the city's best bookstores are booming because people would rather live in fictional meet-cutes than risk a real one.
And then there are the endless rants on TikTok about first dates gone awry and etiquette being a thing of the past. But here's what all of those opinions are missing: New York is still one of the last places where a meet-cute doesn't feel extinct. Where 'anything could happen' isn't such a crazy thought—it's literally how this city works.
And I know this because I've been testing the theory.
Following my divorce, I've been actively dating—one or two dates a week, on average—since January. Am I tired? Yes. But I wouldn't trade it. Not the men, not the stories, not even the situationships turned into heartbreaks. Because each date, each encounter, has confirmed what I already suspected: The possibility itself is the point.
Take one Friday in May. It was hot, one of those sticky, electric New York evenings where the sidewalks shimmer, the air feels charged and everyone's just a little more flammable.
I wandered into a bar alone, ordered a glass of wine and locked eyes with the bartender—let's call him Chance. He moved with the easy confidence of someone who knew he was being watched, and when he winked at me, I felt that rare flicker of hope.
We flirted. He made me a drink (or three) on the house. I left my number on my receipt. Two nights later he came over. Then, like so many New York men, he vanished. Until months later, on another whim, I found myself back at the same bar, face-to-face with him again.
I didn't go back for the bartender. I went back for the feeling I'd had that first night… the high of being brave enough to walk into a place alone, to flirt with a stranger, to open myself up to whatever might happen.
That night I even asked other people at the bar what they loved about dating in New York. Almost everyone, from Gen Zs to thirtysomethings, said the same thing: 'You can meet anybody.' And with that comes the promise of something. Maybe just a fling, maybe something more.
Even the bartender, when pressed, admitted that women often assume he's only flirting to hook up, so they shut down on him (rudely, apparently) before he can make a real connection. And it made me pause—aren't we all doing that? Going on the apps and walking into dates and bars armored in cynicism, assuming the worst before the first drink arrives?
New York teaches you that rejection and loneliness isn't the opposite of love, it's baked into the pursuit of it.
Yes, you risk the proverbial (or literal) bartender not texting you the next day. You risk getting hurt. You even risk disappointing someone else. But that's the deal. There is no reward without risk. And when you're brave enough, kind enough and open enough, the reward isn't always a partner—sometimes it's just the reminder that connection is still possible.
Grief is unavoidable, and none of us will get out of dating—or life—without it. But New York teaches you that rejection and loneliness isn't the opposite of love, it's baked into the pursuit of it.
So don't stop. Don't settle. Don't buy into the rhetoric that dating here is doomed and you're destined to die alone. I'd rather navigate this city solo, chasing its endless ' what ifs?' and ' why nots?,' than close myself off to connection. Wouldn't you?