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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:
Adam: He’s picky, grumpy and hasn’t found the right chemistry in a while.
Mark: He’s a rom-com fan looking for his own perfect meet-cute.
Ideal date:
Adam: A movie after meeting somewhere he can hold a conversation, like a quiet bar or restaurant
Mark: Something that lets him get comfortable, like drinks in the Village before a nightcap somewhere more intimate
THE DATE
First impression
Adam: “He’s a glasses-wearing person; I like a nerdy look. He looked very put together, like he had tried a little bit, but not so much that it was obvious—really that sweet spot.”
Mark: “He was already sitting at our table, reading a book. It showed an air of confidence that he didn’t have to wait for me outside. He was there and ready, which put me at ease.”
Chemistry
Adam: “It never felt like we were sitting there staring into our eggs. Once I figured out [our age difference], it felt like we were less on a date page…but he’s a very sweet guy.”
Mark: “He was so easy to talk to. He seems very comfortable with himself, which made me open up a lot more easily. Since he’s a creator, it was cool to hear about what he does.”
Awkward Moment
Adam: “We had a nice chat, and that was sort of it. I don’t think either of us pushed the boundaries too much. I think we’ve both been on a lot of first dates, so we know the game.”
Mark: “I forgot to bring cash. I tried to Venmo him, but he was like, ‘No, I got it.’ I don’t think he even noticed; internally, [I was] like, He thinks I’m a young kid who can’t pay!”
Afterward
Adam: “We made tentative plans to go to Marie’s Crisis [piano bar]. [Liking that place is] something that we had in common, so it seemed a natural place to hang out again.”
Mark: “He walked me a couple blocks, and we exchanged numbers. We hugged. I’m still figuring out what the chemistry is. I think a second meet-up will clarify things.”
Verdict
Adam: ♥♥♥♥ “If I were going to marry Mark, I’d give him five stars—but I like to leave a little room for improvement. It might be a more friendly thing; it’s still up in the air.”
Mark: ♥♥♥♥ “I was expecting the worst, but he made it really comfortable—and he was cute. I left feeling like I had a great time and met a really interesting person.”
Our daters went to Coco & Cru (643 Broadway, 212-614-3170)
RECOMMENDED: See more Undateables
Want to be set up on a free blind date? Email undateable@timeout.com.