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Natalie and Matt

Each week, we take two New Yorkers who swear they’re totally undateable, and put our matchmaking skills to the test

Will Gleason
Written by
Will Gleason
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Natalie and Matt

Photograph: Ann Sullivan

Why they’re single:
Natalie: She’s newish to New York and just getting the hang of the dating scene.
Matt: He has just recently been trying to focus on himself.

Ideal date:
Natalie: Drinks at an outside bar
Matt: Walking around a park or museum

THE DATE

First impression
Natalie: “I got there first, and we met right by the entryway of the restaurant. My impression was that he was excited. I thought he was handsome, and he seemed kind.”
Matt: “I wasn’t head over heels about her right away, but as we got to talking, I think we hit it off. It was a little awkward at first, but it got better as the night went on.”

Chemistry
Natalie“He kissed me on the cheek when we first met, and I just said, ‘Thank you,’  which was mortifying. We didn’t have a lot in common: He’s into sports, and I’m really into travel.”
Matt: “There was no romantic chemistry, but we were bonding over the atmosphere and the food. We were both really down to eat and try everything.”

Awkward Moment
Natalie: “He talked about his ex for a good 10 minutes. At one point, he called her his girlfriend, which kind of threw me. He talked a lot about a trip they went on together.”
Matt: “There were a few times when the conversation died and both of us didn’t really know where it was going. There were definitely a few awkward pauses during dinner.”

Afterward
Natalie: “Toward the end of the meal, he started choking on a piece of duck. That’s when I found out he was actually a lifeguard at my favorite water park growing up.”
Matt: “We exchanged numbers. She walked me to my station, and then she walked home. There was an awkward kiss on the cheek, and we agreed on a second date.”

Verdict
Michael: ♥♥♥ “It was cool. I wish we had more in common, but I enjoyed the evening. We might see each other again, but I’m a little lukewarm about it.”
Matt: ♥♥♥ “It was really good—a unique experience. I’m interested to see where it goes and how we get along through texting. I would see her again.”

Our daters went to Junoon (27 W 24th St, Flatiron District)

RECOMMENDED: See more Undateables

Want to be set up on a free blind date? Email undateable@timeout.com.

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