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Meet the Undateables: Chelsea and Greg

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.

The date: Dinner at Brindle Room (277 E 10th St)

First impression
Chelsea: “He was cute. He had a beard, and I love a beard. He seemed like my type, someone I would approach. I could tell right away that we had a similar disposition.”
Greg: “I tend to date brunets with bangs, and that’s exactly what she was. She was open and personable. Her hat said her name on it; I liked that.” 

Chelsea: “We had a lot to talk about right away and were definitely on the same level as far as point of view and sense of humor. There’s personality chemistry for sure.”
Greg: “We covered all the bases—we talked about pretzels, death, infinity being unnerving and also the air quality of 1940s Pittsburgh. We definitely got along.”

Chelsea: “I gave him my number. We’d been joking about stalking, so I said, ‘Don’t follow me and murder me!’ He texted later, and when I said I was home, he was like, ‘I know…’ ” 
Greg: “I walked her to the train. I said we should shake hands and hug at the same time, because I’d read these columns and some people just shake hands, so we did that.” 

Awkward Moment
Chelsea: “I spilled the beans to the waiters that it was a blind-date situation, and they were like, ‘That’s so fun!’  They wouldn’t stop checking on us and kept watching us.”
Greg: “I decided to walk to the restaurant, but I forgot my wallet so had to walk fast back home. I jumped in a cab and made it in time but felt rushed, sweaty and flustered.” 

In three words
Chelsea: Greg is "cute, friendly and bearded."
Greg: Chelsea is "thoughtful, funny and pretty."

Chelsea: ♥♥♥♥ “I don’t know if I felt, like, head over heels—chemistry is a weird thing—but I’d definitely be interested in seeing him. Ball’s in your court, Greg. Your move.”
Greg: ♥♥♥♥ “I was definitely attracted to her. I’d like to see her again. She’s extroverted and I’m more introverted, so I think that’s a good personality match.”

RECOMMENDED: See more Undateables

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