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:
Justin: Is an all-or-nothing person, so has to get a strong feeling to go for it.
Matt: Is selective and hasn’t met the right person.
Justin: Going to a concert or biking to the beach
Matt: Drinks and a meal somewhere outside, with lights strung above, followed by a walk through the park.
Justin: “I thought he was really cute. I was happy to see that he smiled instantly—he had a great smile. We immediately started talking. It never felt awkward at all.”
Matt: “Within the first two minutes, I realized we weren’t going to have a bad time. He was handsome and very open but not my type. I tend to go for older, bigger guys.”
Justin: “The conversation kept rolling. We’re both pretty witchy and don’t enjoy light-hearted things—I liked that. I don’t know if there was flirtation, but it was an easy connection.”
Matt: “We never stopped talking. We talked about what turns us on artistically and about ghosts and haunted stuff, and we shat on Sam Smith a little. There was good energy.”
Justin: “We exchanged numbers, but later I thought I’d lost his. I was like, ‘Shit, he’s going to think I’m never going to text!’ Luckily I’d saved him in my contacts and forgot somehow.”
Matt: “He did a Renée Zellweger impression, and I responded with my Drew Barrymore impression. I never expect to do that on a first date. I was hesitant, but he made me do it.”
Justin: “We were there a solid two hours and were still in the middle of our conversation after dessert, so I was like, ‘Want a nightcap?’ We grabbed a drink at Nowhere Bar.”
Matt: “When I got home, I texted him saying I wanted to be transparent and was interested in hanging out again—but as friends. He responded with, ‘Totally, I got that vibe too.’”
Justin: ♥♥♥♥ “I was shocked at how cool he was. But I didn’t feel a romantic vibe. I don’t think we’re meant to be. We’re already talking about meeting up again though.”
Matt: ♥♥♥♥ “It was really fun. I put it in the friend zone, but I’m interested to know more of him in the future. We’re probably going to do something next weekend.”
Our daters went to City Crab Shack (10 E 16th St, 212-529-3800)
RECOMMENDED: See more Undateables
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