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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:
Wes: Too independent, and people have called him cold
A.J.: Can be really picky
Ideal date:
Wes: A stroll through Central Park
A.J.: Italian food with red wine and good conversation
THE DATE
First impression
Wes: “He presented taller than he actually is, because when we first met, I was seated already. I really liked that he was on time. I thought, Okay, I’m meeting someone normal!”
A.J.: “He was very tall and had a nice smile. He had headphones on, so I was worried at first that I was late and he was bored, but I was early—he was really early.”
Chemistry
Wes: “It felt very organic to me. I was shocked by how much we had in common. I have a cockapoo, and he grew up with one. We both like winter more than summer.”
A.J.: “In the first 20 minutes, we kind of both got the vibe we weren’t each other’s type. Once we got that out of the way, it became more friendly than romantic.”
Awkward Moment
Wes: “The roof was retractable, and when it started pouring, they closed it, and we were sitting directly under the seams. It dripped right into his drink.”
A.J.: “He said he likes darker, taller guys, and I’m neither of those things. It was awkward for a moment, but we both laughed about it.”
Afterward
Wes: “He invited me to come hang out with his friends, but I had other plans. He requested me as a friend on Facebook before the end of the date.”
A.J.: “We were both trying to meet up with our friends, but we thought it would be fun to hang out sometime and go to a gay bar, so we did exchange numbers.”
Verdict
Wes: ♥♥♥♥ “I think we’ll end up friends. I told him I don’t have many gay friends. It’s nice to see I can still have a good time with someone who’s not exactly what I look for.”
A.J.: ♥♥♥ “He was a smart guy with a good sense of humor, but I think overall we’re too similar in a lot of aspects, and I’m looking for something different.”
Our daters went to Upstairs at the Kimberley Hotel (145 E 50th St, 212-888-1220)
RECOMMENDED: See more Undateables
Want to be set up on a free blind date? Email undateable@timeout.com.