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Meet the Undateables: Ben and Gray

Written by
Dana Varinsky

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:
Ben: Is shy about pursuing relationships and doesn’t know how to take 
things to the next level
Gray: Is fiercely independent, super busy and 
has a great group of friends 
that keeps her satisfied 

Ideal date:
Ben: Drinks at a bar 
with a mellow atmosphere, then a walk in 
the park
Gray: A picnic 
and an outdoor 


First impression
Ben: “She was extremely pretty. Turns out she’s from Virginia, so she was very friendly. She had a cool denim jacket, and she was really well-spoken, smart and funny.” 
Gray: “He had a ponytail, which normally is not what I go for—my type is more clean-cut. But he seemed really nice and friendly, 
so I was like, All right, let’s do this.” 

Ben: “We had a surprising amount in common. 
I thought there was at least social chemistry. I couldn’t tell whether she was into me, but I think she had a good time.”
Gray: “I didn’t feel an instant attraction to him right off the bat, but we were there for like four hours, and there were never any awkward silences or weird lulls.”

Awkward Moment
Ben: “I’m used to going out with people I’m already in contact with, so I forgot to ask for her number. I didn’t realize I wouldn’t be able to get in touch with her. Oops.”
Gray: “I didn’t want to do the ‘let’s-do-this-again’ dance as we said goodbye but didn’t want to be mean. So I gave him a hug and just ran down into the subway.”

Ben: “We hugged and said something like, ‘Thanks, that was fun.’ And then I went home. My first-date goodbyes are always lame—I haven’t figured that part out yet.” 
Gray: “We’d had six courses, so it was really late, and I was tired. We didn’t exchange information or anything. Maybe since 
I ran away, I didn’t give him a chance to.” 

Ben: ♥♥♥♥ “I had a blast. I thought she was cool and nice. I’m going to pray that someone from Time Out New York asks her if she’ll give me her email address.”
Gray: ♥♥♥ “He was a sweet, good guy. 
I really enjoyed spending the evening with him, but I wasn’t feeling that connection, so I don’t foresee anything happening.”

Our daters ate at Duet Brasserie (37 Barrow St, 212-255-5416)

RECOMMENDED: See more Undateables

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