A 28-year-old law student with two roommates in Washington Heights. A 46-year-old private equity exec and dad of two, from Cos Cob, Conn. A 44-year-old college dean, who traveled all the way from Philadelphia for Sunday brunch.
Welcome to my yearlong dating experiment in NYC — a city famous for its cutthroat singles scene.
It all started in the middle of the night last February, shortly after a 4?½-year relationship crumbled. Lying in bed and squinting through tears, I downloaded Hinge and started scrolling.
I had two goals when I dove back into dating. The first: to have fun, and lots of it. My breakup had been painful, and I wasn’t ready to be vulnerable again.
But I also wanted to meet my future husband. Look, I turned 35 last year and want a family; the next relationship had to be The One. But I could still be cool about it.
See, I’m stubborn and determined. A Type A personality with a work ethic that won’t quit. So I took on the dating scene like I tackled homework in high school, or researched restaurants for my last vacation: obsessively. After all, dating is a numbers game. More dates meant better odds. So I filled my calendar.
‘More dates meant better odds, so I filled my calendar.’
By the end of the year, I’d met with 25 men, gone on dozens of second and third dates, and chatted up contenders until my phone burned hot in my hands. Here’s what I learned from 12 months of chasing romance in NYC.
Dating in NYC is chaos. Embrace it.
Before my year o’ dating, I always figured I’d end up with someone like me: a hard-working New Yorker, an extrovert, a connector. But on Hinge, I decided to open up the applicant pool to those with different résumés.
Everyone always talks about how hard it is to meet people in New York. So I set wide parameters for age and geography, and spent a lot of time combing through profiles in the app’s Discover section. When it came to reaching out or responding to suitors — on the app, you “heart” someone to express interest — I erred on the side of yes.
I definitely wasn’t wanting for options: I found myself matching with everyone from barely legal 19-year-olds (no, we didn’t meet up!) to silver-fox dads. Some people just wanted sex; others wanted something more serious. Creeps were easy to spot — and dismiss — before IRL encounters.
Evenings took me everywhere from the Upper East Side bar Dorrian’s, a brotastic haunt of the young and overeager, to the batting cages at Chelsea Piers. I locked lips all over the city — once, side by side on adjacent docked Citi Bikes before we both pedaled to our respective homes.
‘Some dates … were better fits for the friend zone than the bedroom.’
Yes, I had a lot of weird nights. But I also had some pleasant surprises. My first post-breakup date was with an openly Republican lawyer from New Jersey renting a Financial District pied-à-terre. When he learned my favorite food was chocolate chip cookies fresh from the oven, he bought raw dough to have on hand when I came over. On the flip side, some dates who seemed the most similar to me on paper — a journalist, say, or an NYC native — were better fits for the friend zone than the bedroom.
If you care, get personal.
Some people swear by stock pickup lines, but I think it’s tough enough to make a connection online. So when I was really interested in someone’s profile, I sent a specific message about one of their photos or interests. To a cute athlete: “Hello! I’m a runner too, and your CHEESY Swiss joke made me chuckle out loud.” To a pop-punk fan: “Blink-182 has SUCH good karaoke songs.”
That strategy held true true offline, too. When I met a guy who shared my love of architecture, I brought him to the Grand Central Oyster Bar — a favorite, in part, because of the arched ceilings lined with Guastavino tiles. I knew he would appreciate it as much as I do.
When men shared my philosophy, I noticed. Small gestures moved me, from flowers on my birthday to personalized playlists to someone buying The Post expressly to read my work.
You’re not too busy to date.
Like most New Yorkers, I’m busy. But I wanted to go on as many dates as possible, without sacrificing work or family or friends. That required a lot of organizing and planning — which, luckily, is something I excel at.
To avoid wasting excess mental energy on trivial stuff, I systemized my dating look. I found a go-to first-date outfit: well-fitting jeans, cute flats and a sleeveless paisley blouse that showed just the right amount of cleavage (or a white eyelet shirt, if I was tan). I kept a makeup bag at my work desk, so I’d always be ready to roll.
Instead of clearing my calendar for dates, I wove men into my plans. I brought guys to post-softball-game drinks and a friend’s ugly-sweater party. To avoid losing hours commuting, I scheduled the bulk of my dates near my Upper East Side neighborhood. When that wasn’t possible, I made sure the meet-up was at a bar or restaurant I wanted to try — a soup dumpling spot in Flushing, for example.
I got good at this. I even managed to make time for romance when I flew to Las Vegas for a conference: One fortunate guy met me for a romantic weekend of hiking, eating and putting a hotel room to good use.
Games are for insecure 20-year-olds.
There were too many guys, and not enough time. So I didn’t follow “The Rules” — waiting a few days to text after a good date, not sleeping with someone until the third date. That stuff is stupid, and it doesn’t work.
‘There were too many guys, and not enough time.’
Some women don’t like to eat in front of guys. Screw that. Years in a relationship had reduced my weeknight tolerance, and if I’d been ashamed to order food, I would have paid with a hangover.
Finally, I decided to be honest — even if it risked turning people off. I told men that I was still hurting from my breakup, that I was afraid to be tied down. Anyone who I had a real shot with would need to understand that, and being myself made the dating process feel like less of a burden.
Playing the field is fun and exciting — but you can’t do it forever.
Dating burnout is real. Looking back, I can see the signs that I was getting a little too deep in the Hinge binge.
There was my flirtatious “I had a great time last night!” text .?.?. sent to someone I hadn’t met yet. The times I accidentally ghosted some lovely guys. The jolt of anxiety I felt X-ing away a potential suitor.
‘I was getting a little too deep in the Hinge binge.’
I was so laser-focused on finding the “perfect” person that I freaked out when I met someone I actually liked.
Remember that Grand Central Oyster Bar date? It turned into a second, third and fourth rendezvous — all in one week. I was having a blast, but hesitated to commit.
“What if the next person who shows up on Hinge for me to ‘heart’ is actually my future husband?” I wailed to a friend.
A year after I downloaded Hinge, dude No. 24 and I will spend Valentine’s Day together. He’s English, actually likes romantic comedies and is an exceptional cook. We’re planning to take a photography class together, and we’ve booked a trip to the Caribbean.
Are we living happily ever after? Not yet. But I’m happy for now — and relieved to trade my first-date jeans for pajama pants.