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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:
Lindsey: "She can’t find enough people who have similar interests and are into more than just kicking it."
Guy: "He hasn’t found a girl who’s ready to have a serious relationship."
Ideal date:
Lindsey: "Go see a horror movie and get drinks after"
Guy: "Meeting in Union Square and then just sitting on the steps and people-watching"
THE DATE
First impression
Lindsey: “He looked like a pretty typical twentysomething guy. Nothing really stood out. He was just like any guy you’d meet at a bar. He was a little awkward.”
Guy: “Once she sat down, I recognized that I’d be punching above my weight for the rest of the night. She was really pretty. The conversation was easy right from the start.”
Chemistry
Lindsey: "He had a great sense of humor. But he kept saying he only wanted to ask the important questions. He wouldn’t answer any questions like ‘What do you do?’ ”
Guy: “Definitely more of a friend vibe. It was more like we were exploring the menu together; we were both taking notes on the food and reviewing it as we went.”
Awkward Moment
Lindsey: “He literally took out a notepad and was taking notes the entire night. I don’t think it was a me thing, I think he’s just a note taker. The entire night.”
Guy: “A lot of the plates came with little bonito flakes, so they kept bringing jars over. Eventually, they were all over the table, so we started to get buried in bonito flakes.”
Afterward
Lindsey: “We walked out of the restaurant and were like, ‘Okay, bye!’ It didn’t feel weird, it just ended on a friendly note. I thought he might ask for my number, but he didn’t.”
Guy: “At the end of the night we just kind of smiled and gave each other a shrug and were like, ‘See you around!’ It was a great place to leave it—just a casual New York thing.”
Verdict
Lindsey: ♥♥♥ “He’s an awkward guy, which is fun on a friend level but not on a date level. Also, PSA to all dudes in all boroughs: Don’t take notes on a first date, please.”
Guy: ♥♥♥♥ “It was fun. She maybe brought up like two or three times that she is definitely undateable. I would just really like her to know that she is absolutely dateable.”
Our daters went to Sen Sakana (28 W 44th St, 212-221-9560)
RECOMMENDED: See more Undateables
Want to be set up on a free blind date? Email undateable@timeout.com.