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Photograph: Kelsey Dubinsky

Meet the Undateables: Daniel and Alex

Will Gleason

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.

Photograph: Kelsey Dubinsky

Why they're single:
Daniel: He has unrealistically high expectations and a fairy-tale idea of finding the right person.
Alex: He’s busy with work and can come off as guarded and a little inaccessible.

Ideal date:
Daniel: Dinner then a walk through an unfamiliar neighborhood
Alex: Dinner followed by an outdoor activity, if the weather’s nice


First impression
Daniel: “Alex arrived on time, which I appreciated. We shook hands, and then he sat down and jumped right into questions. He seemed really interested in getting to know me.”
“He came off as a bit guarded. I don’t want to say that he was cold, but I could tell he was more Type A and likes to be in control. I can read people really well.”

Daniel: “I got more of a friend vibe, but the conversation was good. We covered a lot of taboo first-date topics like race and religion. We even talked about genocide.”
Alex: “I thought he was super attractive, physically. He also seemed really smart, which I like. I’m not a very intellectual person. I’m kind of a dumb-ass fool.”

Awkward Moment
Daniel: “He made a comment that he was using the word ‘bougie’ too much. After that, I started keeping count and he kept using it. I think the count got up to eight.”
“A little bit of sex talk came up, and I think he got uncomfortable. Maybe he isn’t used to talking about his sexual history, but that stuff doesn’t really bother me.”

Daniel: “After dinner, we walked around the neighborhood, and the conversation got more personal. When we got to my subway stop, we hugged and exchanged numbers.”
“At the subway, he went in for a kiss but was a step down from me, so it was kind of awkward. I gave him another goodbye kiss, and that was good. Right on the lips.”

Daniel: ♥♥♥ “It was fun to meet someone new with no preconceived notions. I’d like to keep in contact. I didn’t get a romantic vibe, but I think a friendship is possible.”
Alex: ♥♥♥ “I would definitely go on a second date with him. I liked him, there was chemistry, and I would probably entertain the idea of dating him.”

Our daters went to Vinateria (2211 Frederick Douglass Blvd, 212-662-8462)

RECOMMENDED: See more Undateables

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