Each week, we take two New Yorkers who swear they’re totally undateable, and put our matchmaking skills to the test. Afterward, we find out what went well on their date, and what went horribly, horribly wrong.
Why they’re single:
Daniel: He’s never been able to figure out the shenanigans behind dating—and also talks a lot.
William: He’s a hopeless romantic living in the wrong city and using the wrong apps.
Daniel: Meeting up for drinks for an hour and then spitballing from there.
William: Something active like yoga or a run in the park followed by brunch.
Daniel: “I got to the restaurant about 10 minutes late, which is like New York—early, and when I first saw him, I was like Oh, cute kid! He was my type and seemed very friendly.”
William: “He was definitely cute, really tall. I was like If I had to do this with someone, this is not a bad option. But I usually go for someone who looks a bit more professional.”
Daniel: “He reminded me a lot of a coworker, and once I realized that, I couldn’t get it out of my head. I can’t think sexually about someone who reminds me of a good friend.”
William: “It’s felt really natural, almost like we were friends before. It didn't feel like a date. He really played off my sarcastic jokes, and we never scrounged for things to talk about.”
Daniel: “I haven’t been on a date in like six months and was kind of nervous. At one point, I took a bite of asparagus, and it fell off and completely splattered my food.”
William: “As we were leaving, instead of exchanging numbers, he gave me his business card. I just thought that was kinda of strange. I couldn’t tell if he wanted to meet up again.”
Daniel: “We left the restaurant and walked to his subway stop, which was about a block away. I gave him my card, we hugged, I gave him a kiss on the cheek, and that was it.”
William: “We hugged, and then he went in for a kiss on the cheek. My first instinct is to just hug goodbye, so I was a little taken off guard. I didn't really reciprocate.”
Daniel: ♥♥♥♥ “It was a good, standard first date. Nothing was like, Oh my god, we have to see each other again, as soon as possible. But it wasn’t like get away from me.”
A.J.: ♥♥♥♥ “From a love-match potential, I feel like we'd have to go out a few more times to see if something was really there. I'd definitely be open to meeting up again.”
Our daters went to Benares (212-766-4900, 45 Murray St)
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