As a 28-year-old woman in New York City whose relationships have never lasted past the six-month mark, I know my way around a dating app. Hinge, Bumble, Tinder, Raya ― I’ve swiped through them all. My experience in this field didn’t make a difference, though. No matter the platform, the options were the same: men who either wanted a casual hookup and were upfront about it (fine) or wanted a casual hookup but claimed they were looking for something more (what does “short-term relationship open to long” even mean, Tyler?).
For as long as I’ve been dating, apps have been at the center of every first kiss, Thursday night fling, and Sunday morning regret. In college, they were an easy way to figure out which cute guys on campus were single. As a young adult in the city, they made casual hookups effortless. But now, as someone looking for a real relationship, navigating them feels impossible. Some of my friends have been lucky enough to meet their boyfriends this way, but for most single women, it’s just an endless loop of men who want something casual ― or worse, a man whose idea of a first date is taking you out on his fishing boat (true story). It’s hard not to doom-swipe through the options, hoping for something different.
There are offline options, of course. You’d think that living in one of the biggest cities in the world would make in-person dating easier — but, sincerely, it does not.
Meeting someone at a bar? Practically unheard of. On a Saturday night in Williamsburg, everyone’s focused on their friends, the music, and maybe grabbing a halal cart chicken and rice before heading home. Nobody approaches anyone. Nobody is looking for an in-person connection. The uncertainty is too daunting, the effort too much. And maybe it’s not just about convenience, but conditioning. We’ve spent years shifting our lives online, texting instead of calling, DMing instead of calling to make plans, ordering food without speaking to a single human. Conversation happens through screens first, faces second. And thus, dating stays confined to the apps. Back to square one.
Fed up with the relentless cycle, I recently deleted my dating apps and decided to try meeting people in the wild, as my friends and I like to say. One of my besties told me about a new dating experience they wanted to try called 222, a platform that curates IRL social spaces with the goal of helping like-minded people hang out. I was down to try anything, and this seemed like a good enough experience as any to break free from the grip of online dating, and maybe, just maybe, meet someone in a way that didn’t start with a swipe.
After filling out an extensive questionnaire and waiting a few days, I was finally invited to my first event ― a small dinner at Au Za’atar, a Lebanese restaurant in the East Village, followed by a larger gathering at a nearby vinyl bar. Naturally, I was nervous, but years of working in the media has trained me to make conversation with even the most reserved people. My friends like to joke that I could talk to a brick wall and somehow, it would talk back. So regardless of who showed up, I knew I’d be fine. But the real question is: Could I meet someone worth pursuing a relationship with?
When I arrived, I met a small group of men and women, all there with the same intention of making real-life connections. Naturally, I focused my energy on the men in the room, hoping for a spark, but I was quickly disappointed. Not because they weren’t nice (some were) or because they weren’t interesting people (they might’ve been), but because the conversations were just… fine. Vanilla, at best. And I was looking for even a whiff of rom-com energy.
What I noticed right away was that the straight men struggled with small talk. And honestly, I couldn’t even blame them. After years of dating online, meeting in person can feel awkward, even disorienting. Eye contact is an art, and holding it for too long can go from sweet to psycho real quick. There’s no time to type, erase and retype the perfect response. You have to be quick, engaged and able to carry a conversation in real-time. That’s a skill ― one that, for many of these men, had clearly gone unpracticed for too long.
The women in the group? No problem there. Making platonic commitments wasn’t even on my radar ― my schedule is chaotic enough, and the last thing I needed was more social commitments ― but from the moment we started talking, I was drawn in. They were smart, funny and effortlessly cool, the kind of people you meet and immediately think, how are we not already friends?
Before I knew it, these women and I were sharing appetizers, swapping jokes and bonding over the mutual exhaustion of navigating the New York dating scene. The conversation flowed effortlessly, it wasn’t just a one-sided exchange propped up by my ability to talk nonstop.
By the end of the night, I had a handful of new phone numbers and Instagram handles, along with tentative plans to grab drinks or try a new restaurant together soon. It wasn’t what I came for, but in a way, it felt like the real success of the night.
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While I’m still looking for a romantic partner, the speed dating experience made me realize that the women I meet in this city are often more likely to embrace new experiences, joy and whimsy. I sense a like-minded zest for new experiences, whereas the straight men I meet seem stuck in their own routines, perhaps for fear of change or rejection. And while I understand this is all social conditioning, it often makes sparking IRL connections with them kind of exhausting.
But when women come together, the energy shifts. There’s a shared sense of possibility and understanding, inclusive of our dating woes, that’s magnetic. That night, it was a reminder that when we connect, magic happens, and the world feels a little more alive. And that makes anything possible — even eventually, somehow, finding love.
