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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:
Jason: Hasn’t found a woman who’ll buy him a drink yet
Vanessa: Has a low tolerance for awkward drinks and conversation
Ideal date:
Jason: Making no plans, walking around and acting like tourists
Vanessa: Skipping the get-to-know-you stuff and taking a weekend or day trip
THE DATE
First impression
Jason: “I was pleasantly surprised. She’s really cute. She has nice blue eyes. I don’t have a type—to have one is kind of closed-minded—but she was definitely attractive.”
Vanessa: “He was at the first table when I walked in. He was nice, friendly and approachable. He had an earring that I wasn’t into—it was a little Hot Topic–y for me.”
Chemistry
Jason: “In the beginning, I was like, ‘Yo, you’re pretty good-looking, why are you undateable?’ That put us at ease. We had that vibe where we could chill and talk.”
Vanessa: “Overall I think the conversation went well. We talked a lot about work, but that’s not as boring as it sounds. He’s a very genuine person. It wasn’t forced or phony.”
Awkward Moment
Jason: “In the middle of our conversation, sometimes she would spin her straw in her drink. It made me want to ask, ‘Am I boring you?’ But I didn’t want to be rude.”
Vanessa: “I gave him my business card, and he made a comment because my cards say HELLO on them. I got them before the Adele song, but now they’re kind of loaded.”
Afterward
Jason: “I asked, ‘Hey would you want to hang out again?’ That seemed awkward. She gave me her card and went downstairs. No hug, unfortunately, but I wasn’t stressing it.”
Vanessa: “We were there for two hours talking. I had to be up early the next morning, so I said, ‘Okay, let’s get out of here.’ We rolled out, walked to the subway, and that was it.”
Verdict
Jason: ♥♥♥ “I’ve had dates where it’s like, ‘I fucking like you,’ and this wasn’t one of them. But I’d definitely be willing to hang out and get to know her more.”
Vanessa: ♥♥♥ “He’s easy to talk to, but I didn’t see us dating. He’s in school, and I totally respect that hustle, but I need someone who’s not in a transition phase.”
Our daters went to Broken Spoke Rotisserie (439 Third Ave, 212-889-6298)
RECOMMENDED: See more Undateables
Want to be set up on a free blind date? Email undateable@timeout.com.