Dating Science

Valentine’s Day may be the most sentimental of holidays, but every year, it seems, dating gets less romantic. We’re living in an era, after all, where emoji-littered text messages pass for love letters and not tweeting about a one-night stand is an act of chivalry. With more than 40 million singles now pouring their hopes (and money) into web-based matchmaking services, we don’t just online-date anymore—we niche online-date. (Into cats? is here to serve you. Prefer salt-of-the-earth types? Try When it comes to fix-ups, we still weigh the two cents of meddlesome mothers and well-intentioned friends, but now we also consult professional wingmen, dating coaches, and the “best matches” spewed forth by data-crunching websites. On the following pages, in an effort to take the pulse of the current dating landscape, we conduct two experiments in modern romance—and take a gander at what passes for a hot pickup line on

The Yenta Experiment
Who makes the better Cupid: a Jewish mother, an ex-boyfriend, or the algorithms of OKCupid? An intrepid single goes on three arranged dates to find out.

Lysee WebbPhoto: Victor Prado/New York Magazine

The Bachelorette:
Lysee Webb
27, talent booker and record-label associate
“I’ve been single since the beginning of last year, after dating a string of long-distance boyfriends. I tend to go for musicians, but it’d be nice not to, as their music always comes first and they’re constantly on the road. On the other hand, everyone loves a musician.”

Photo: Victor Prado/New York Magazine

1. The Yenta:
The dating service

The Bachelor:
Nicholas Shelestak
32, musician

OKCupid says: Nicholas and Lysee have a 91 percent compatibility match, a value determined by calculating their answers to a series of questions, the weight they assigned to each of those questions, and how they preferred potential dates to answer.

Lysee says: “He lives in Williamsburg and asked if I wanted to meet him there. I said ‘No, it’s nineteen degrees out, and I live on the Upper West Side.’ So I suggested the West Village, and he picked this cute old-timey bar called Orient Express. He’s in a band, so we immediately started talking about that. He totally embodies my type: a thirtysomething jaded musician who is kind of angry. It’s like I’ve dated him before.”

Nicholas says: “I was not immediately put off when I first saw Lysee, which is a good thing. We had a nice long chat and plenty in common. There was talk about touring and all the bands I’ve played in. She said she was best friends with her ex, though, which I’m not sure I’d be comfortable with. In my history, that’s never turned out well. Also, she’s not really my type. I go for taller girls who are a little more artsy. I might see a concert with her, but I wouldn’t go on a second date.”

Photo: Victor Prado/New York Magazine

2. The Yenta:
The ex-boyfriend, Matt Hislop

The Bachelor:
Matt Badger
27, video editor

Matt H. says: “I wanted to find someone outside of Lysee’s normal social circle. She tends to go for pretty boys, and likes guys who are doing something with their lives but are also creative. Matt works as a video editor at an ad agency.”

Lysee says: “He picked Bar Veloce on Seventh Avenue. Right away, he was really friendly and engaging, asking me a lot of questions. We talked a lot about basketball, as Matt had just been to a Nets game against the Golden State Warriors. I was surprised he didn’t know who Steph Curry was, but I’m psychotic about that stuff. I like that he was really passionate about his job, and he was totally cute, but there just wasn’t any chemistry.”

Matt says: “She came in wearing cutoff shorts, tights, and a fur coat; she’s a very pretty girl, for sure. She also has, like, an encyclopedic knowledge on rock and roll, but music is not something I follow closely. I normally go for somebody who’s a little nerdier than her. Like, I gobble down movies on Netflix, I’m a little goofy, I’m a little loud and loose, and she’s a bit quiet, straighter to the point. I’m a hugger, so I gave her a hug good-bye, but there was no love connection.”

Photo: Victor Prado/New York Magazine

3. The Yenta:
The mom, Gail Webb

The Bachelor:
Jeff Bigner
27, financial analyst

Gail says: “Jeff is much more corporate than Lysee is used to; I don’t think she’s ever dated anyone who had to wear a suit to work. But he seems like a fun guy, and he’s friends with someone I trust—not to mention, easy on the eyes.”

Lysee says: “He suggested we go to Boqueria, a tapas place in Soho. He studied abroad in Spain and ordered for us in Spanish, which I thought was cute. He was a great reminder not to judge a book by its cover: He was wearing a suit but naming all these cool bands that he likes and telling me he goes to Brooklyn a lot to see shows. One thing I look for when I date guys is whether they’ll mesh with my friends, and I think Jeff would. I’m thinking about bringing him to a friend’s Super Bowl party.”

Jeff says: “She is definitely my type, looks-wise. We clicked from the beginning. We talked about music, basketball, our siblings—it was just so natural. Our dinner lasted till about 11 p.m., and when we left, Lysee asked which subway was nearby. I thought that was awesome: She’s not high-maintenance, and I didn’t need to hail her a cab. It was also nice that she wanted to walk to the subway together—like, let’s hang out a little bit more. I gave her a hug good-bye, but we’re actually going out again next week.”

Winner: Jeff and Lysee hit it off so well, they’ve already been on two more dates—and Jeff did, in fact, make it to her friend’s Super Bowl party. “He has a corporate job, but I like that he’s not defined by it,” says Lysee. “He doesn’t take himself too seriously.”

Dating Science