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.
Our daters had drinks and appetizers at Pergola (36 W 28th St., 212-679-4842)
Mark: “I was a little thrown by her name, but she was pretty attractive and normal-looking. She seemed friendly and open. There was no awkward start.”
Chandra: “He was very polite, but I wasn’t attracted to him. I like grungier guys. He had glasses and a button-up. He reminded me of someone who’d work for my dad.”
Mark: “We talked about the usual stuff—a pretty standard first date. We didn’t have a lot in common. She’s artsy and into indie music. I’m more of a sports guy.”
Chandra:“We talked about generic things, like where we grew up. There weren’t any awkward pauses. The conversation was pleasant. It just felt a little forced at times.”
Mark: “I don’t even know how we got into it, but we started discussing deaths in the family. It didn’t bother me, but it might have been a weird thing to bring up.”
Chandra: “The cocktail I ordered looked like something Don Draper would drink, and his was tall and pink with fruit in it. He was like, ‘We’re reversing the roles here!’”
Mark: “The owner invited us to sit at the bar, so we hung out a little while. Then we hugged and exchanged numbers. She’s a nice person, but I don’t plan on reaching out.”
Chandra: “We finished our drinks, and then we left, and he was like, ‘Should we exchange phone numbers?’ I said sure, but there was definitely no love connection.”
Mark: “I enjoyed it overall, but it wasn’t the super great first date you could have, which I’m not even sure exists. Romantically, I didn’t see sparks.”
Chandra: “It was kind of like a stale cracker, a little boring. He had a good personality, but it didn’t mesh well with mine. He was just not my cup of tea.”
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