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.
The date: Dinner at Good Restaurant (89 Greenwich Ave)
Sam: “I was relieved he wasn’t a creep. He seemed perfectly nice but not my type. I go for taller and more athletic-looking guys. He had an elaborate mustache—a little over-the-top.”
Young: “I thought she was cute and probably a little out of my league, to be honest. I haven’t gone on many dates, so talking to any pretty woman catches me off guard.”
Sam: “He was really interesting and easy to talk to. He’s younger than me, but he was mature. I wouldn’t say there was any romantic chemistry on my end, though.”
Young: “It’s hard to pick out what merits “romantic.” We both like wine—that was something we connected over. I’m not sure I got any romantic feelings from her.”
Sam: “He gave me a papier-mâché rose that he’d made, which I could have written off as cheesy, but it was sweet. We hugged and went our separate ways.”
Young: “I asked if she wanted to exchange numbers, and I think she welcomed it. I handed her a little paper rose that she said she’d keep in her office. I don’t know if it will hold true.”
Sam: “There was a moment with the bill, but before I could get my card out of my wallet, he’d thrown his down. He didn’t say anything, but I didn’t want him to feel obligated to pay.”
Young: “We wound up ordering two glasses of the same wine, so I felt embarrassed that I didn’t suggest ordering a bottle. She said something like, ‘Lesson learned.’”
In three words
Sam: Young is "genuine, polite and engaging."
Young: Sam is "health-conscious, open-minded and career-focused.”
Sam: ♥♥♥ “I’m really glad I went, but I just wasn’t physically attracted to him. He’s worth staying in touch with, but I wouldn’t see him again in any romantic sense.”
Young: ♥♥♥♥ “It was very pleasant. It’s nice to know someone from a completely different background. I’d certainly like to contact her soon for a wine tasting down the road.”
RECOMMENDED: See more Undateables
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