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Meet the Undateables: Drew and Jen

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:
Drew: Doesn’t want to be in a relationship just for the sake 
of having one and isn’t 
willing to settle
Jen: Is still 
waiting for the right 
person to have an 
adventure with

Ideal date:
Drew: Dinner 
followed by drinks 
at a dive bar 
Jen: Dollar pizza 
and the park


First impression
Drew: “We started chatting and ordering as soon as she arrived. She was very attractive and dressed well. She had on a dress and heels, but I was in a T-shirt and jeans.”
Jen: “We shook hands—maybe we should 
have hugged, but that seemed more natural. He had a nice smile and positive energy. He seemed excited to be there.” 

Drew: “It was like a regular awkward first date, like where are you from, how long have you been in New York type of things. I talk a lot when I’m nervous. She was a good listener.”
Jen: “He told a lot of stories—I learned a lot about him. He said he was nervous and apologized for speaking a lot, but I don’t think he asked one question about me.”

Awkward Moment
Drew: “The staff came over and placed down 
two plates, then realized we hadn’t even ordered yet, looked at us and took them away. I didn’t ask why."
Jen: “He started the conversation by telling me that an ex signed him up for this and they still talk. Those things come up, but maybe they shouldn’t in the first five minutes.”

Drew: “We walked to the corner, and when a cab pulled up, I helped her in and sent her off. It was a very benign goodbye. I didn’t really feel the urgency to see her again.” 
Jen: “I hailed a cab, hugged him goodbye, said, ‘It was nice to meet you,’ and that was it. 
I wasn’t surprised he didn’t ask for my number. I would have been fine either way.” 

Drew: ♥♥♥ “She was sweet and pretty, but there wasn’t that spark you look for. 
I like someone with a little more spunk, someone feisty and uncontrollable.”
Jen: ♥♥♥♥ “He was nice, but the conversation felt like one person hitting a ball against a wall. He’ll make somebody happy, but I don’t think I’m that person.”

Our daters went to Beauty & Essex (146 Essex St, 212-614-0146) 

RECOMMENDED: Find more Undateables

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