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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:
Ada: Schedule is really weird, and gets out of work super late
Martin: Has a tendency to overthink things
Ideal date:
Ada: Go to a bar and then take a nice walk around the city
Martin: Walking along the Hudson and then a rooftop bar for a drink
First impression
Ada: “I felt like a jerk because I was super late, but he was so great about it. And I just kept apologizing, and he was like, ‘No, it’s fine.’ It was really nice.”
Martin: “She was really apologetic about being late. I think she came from work, and I came from work, so we were both in casual clothes. She looked attractive.”
Chemistry
Ada: “The conversation was fluid and really easy. There were probably one or two awkward pauses, but we just called it out and laughed about it.”
Martin: “I usually like shorter girls with brown hair. But we spent, like, four hours together. She was a really cool person to talk to, and we laughed the entire time.”
Awkward Moment
Ada: “We were being awkward with the food because it was very different. But we sort of egged each other on to be adventurous and try all of it.”
Martin: “We were walking outside, and she didn’t want to smoke. She finally said, ‘All right, I gotta smoke.’ It was fine; I used to smoke. But she was really nervous about that.”
Afterward
Ada: “We ended up grabbing a drink at another bar, and we talked more about what brought us to New York. He caught me a cab, and we hugged and exchanged numbers.”
Martin: “After the bar, we waited for a cab. It was kind of awkward because it took a really long time. But we just kept talking, and then she left.”
Verdict
Ada: ♥♥♥♥♥ “It was a surprisingly good time. He was a really great guy. He was easy to talk to the entire night, and he had an amazing smile.”
Martin: ♥♥♥♥♥ “She was a really sweet person. I didn’t really have any expectations, but she knocked it out of the park as far as being a good dinner date.”
Our daters went to Pearl & Ash (220 Bowery, 212-837-2370)
RECOMMENDED: See more Undateables
Want to be set up on a free blind date? Email undateable@timeout.com.