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:
Claire: She really likes being single and doesn’t have the time to date.
Tyler: He’s eccentric and hasn’t found someone who’s tolerant of that.
Claire: Grabbing some tacos and Modelos at Rockaway Beach in the summer
Tyler: Something physical like rock climbing
Claire: “It was a sports bar, and I don’t sport, so I was a little out of my element before he got there. But once he arrived, I thought he was very charming, outgoing and cute.”
Tyler: “She was really pretty. She seemed confident and excited to be there. I don’t know, I think I was expecting someone to be a bit more self-conscious or nervous.”
Claire: “There were some romance vibes. I’m really independent, and he said he’s not looking for a girlfriend as much as a partner. So there were definitely some similarities there.”
Tyler: “I think there was a lot of chemistry. We were talking pretty much nonstop. I think we were getting along really well. She’s really strong-willed and opinionated.”
Claire: “I told him I was nervous that he was going to be a Trump supporter, and then I was like, Oh, right. Politics isn’t exactly good first-date talk.”
Tyler: “We were at a table that was almost in the middle of a dance floor, and someone took a picture of us, which was kind of weird. It felt kind of voyeuristic.”
Claire: “We were both taking the same train but didn’t know it. We said goodbye outside the restaurant and then ended up walking and riding the train together a few stops.”
Tyler: “We exchanged information, hugged and said goodbye. I’ve been sending her a barrage of desperate text messages since then.”
Claire: ♥♥♥♥♥ “It was fun. I laughed a lot, we have a similar sense of humor. I was pleasantly surprised that it went well, and yeah, I don’t know. I’d see him again.”
Tyler: ♥♥♥♥♥ “I was expecting someone a little harder to talk to, and it was really easy to talk to her. She was really nice, and I wasn’t embarrassed at all to be seen with her.”
Our daters went to The Ainsworth (112 W 26th St, 212-741-0645)
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