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:
George: Everyone in New York always thinks they can do better or finds a deal breaker.
Emily: Doesn’t put herself out there very much or do any online dating.
George: Going to the Met and having cocktails on the rooftop.
Emily: Going for a bike ride along the Hudson then eating dumplings in Chinatown.
George: “I was there two minutes early, but she’d gotten there before me. I didn’t go in with high expectations, but she exceeded them. She was attractive and pleasant.”
Emily: “He seemed genuinely excited to be on the date. He had on a nice leather jacket, which I liked. He was pretty laid-back. He kind of gave me a Joey from Friends vibe.”
George: “I think a guy should do 80 percent listening and 20 percent speaking on a date, so I asked a lot of questions. She’s interesting—there wasn’t a dull moment.”
Emily: “We had good conversation—I enjoyed learning about him. I didn’t want to immediately jump his bones, but historically that hasn’t worked out for me anyway.”
George: “My mother taught me not to say everything off the bat. But I did mention that I have a daughter; if someone asks about my family, not talking about her is disingenuous.”
Emily: “He was definitely texting with his mom during the date—a little weird, but I wasn’t surprised. I keep running into these mama’s boys. I thought it was funny.”
George: “I walked her to the train station, and we just kissed on the cheek. She took the initiative to give me her card, so I texted her to say, ‘Thanks, I had a good time.’”
Emily: “He offered me a piece of gum after the meal, and I wasn’t sure if that meant he was hoping to make out. I declined the gum, and we just hugged goodbye.”
George: ♥♥♥♥ “The jury is still out as far as a connection, but I had a great time. We said we’d see each other, and I wouldn’t say that just to be nice. So I think we will.”
Emily: ♥♥♥ “I don’t know if I felt any serious sparks, but we had a really good time. I guess it’s too soon to tell. If he wanted to go out again, I’d definitely go.”
Our daters went to Tanner Smith's 204 W 55th St (646-590-2034)
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