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:
Zachary: "Finds the whole online dating thing a little overwhelming—it’s hard to pick someone."
Ned: "Has found that the city is not as easy to navigate as it looks in the movies."
Zachary: "Meeting at a bar, then going for a walk in a park."
Ned: "Something that isn’t a candlelit dinner, like going to a museum or learning how to cook something."
Zachary: “I was there first, and then he came and introduced himself. He had a warm smile. He seemed really nice. He looked a little nervous, but that’s pretty normal.”
Ned: “My first reaction was, Thank God, he doesn’t look crazy. He was dressed casually and looked like a nice guy, which is what I’m looking for. He was kind of reserved.”
Zachary: “As the night went on, the conversation felt forced. He asked me questions, I responded, then asked him the same—the answers didn’t guide the conversation.”
Ned: “We talked about family, traveling, favorite foods, where we live—the basic 101 of dating. By the time dessert came out, we were running out of things to say.”
Zachary: "We never exchanged numbers—I wasn’t sure if he was going to ask, but I didn’t feel inclined to. Neither of us acknowledged that we weren’t going to hang out again.”
Ned: “There were a bunch of awkward pauses in the conversation. Whenever we had one, I was thinking, Oh, man, how long have we not been talking?”
Zachary: "He goes to bed pretty early, and it was a weekday. I guess we were both getting a little tired, so we decided to be done. He walked me to my train and we hugged.”
Ned: “I thought, What’s the next step? Is it worth exchanging numbers? And I didn’t do it. We hugged and said have a safe trip home, he walked away, and that was it.”
Zachary: ♥♥♥ “It was a standard date where there wasn’t a connection.We didn’t have friction—there was no chemistry. I guess we just have different life experiences.”
Ned: ♥♥♥ “It was a stereotypical first date—I’d say mildly average. Zach is nice, but there wasn’t much chemistry. He wasn’t my Starbucks lover, as Taylor Swift would say.”
Our daters went to David's Café (110 St. Marks Pl, 646-678-3206)
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