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Meet the Undateables: Keith and Scott

Written by
Dana Varinsky
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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:
Keith: Is really 
shy about approaching cute 
guys, so almost never 
hits on anyone, and is 
kind of picky
Scott: Hasn’t had luck with dating apps and living on Long Island makes it hard 
to meet people in the city

Ideal date:
Keith: Drinks at 
a nice, dimly lit 
wine bar
Scott: Grabbing 
a coffee and walking around Central Park

THE DATE

First impression
Keith: “He was cute but not my typical type. 
I’m from Washington, D.C., so I like preppy, traditionally good-looking guys. I’ve gone for blonds mostly, and he was brunet.” 
Scott: “He was cute and in good shape. He seemed like a nice guy who had his stuff together. I thought he was older, but I realized he wasn’t so old.”

Chemistry
Keith: “He was pretty nervous off the bat, but we bonded over the fact that we were both fat kids growing up. We had playful banter, but there wasn’t a ton of chemistry.”
Scott: “The date felt mostly businesslike. It never got flirty or anything. It was hard to read him. You could just tell it wasn’t going to go anywhere after that night.”

Awkward Moment
Keith: “When we were leaving, the hostess wanted to take a picture of us. I didn’t know what to do, so she took it on her phone. It’s just living there now.”
Scott: “Within the first five minutes, he brought up that his friend signed him up for this, I think to play it cool. He mentioned it twice. Like, I heard you loud and clear!”

Afterward
Keith: “We took the subway together, and I think 
I said, ‘Add me on Facebook.’ He gave me his business card, but I wasn’t entirely sure if I wanted his number.”
Scott: “He told me to add him on Facebook, and 
I was like, ‘I don’t even know your last name.’ I handed him my card so he has 
my number, but the ball’s in his court.”

Verdict
Keith: ♥♥♥ “It was more like this was 
an enjoyable evening rather than this is someone I definitely want to see again. It was a good date, but I wasn’t blown away.”
Scott: ♥♥♥ “He was a nice guy but no chemistry. I’m a firm believer in giving it two dates, so I’d see him again, but it didn’t seem like we’d be going in that direction.”

Our daters went to Blaue Gans
 (139 Duane St, 212-571-8880)

RECOMMENDED: Find more Undateables

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

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