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Meet The Undateables: Chad and Jules

Will Gleason
Written by
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.

Why they're single:
Chad: He’s too busy and not really looking for anything serious right now.
Jules: She hasn’t been living in New York long and has found it hard to meet people.

Ideal date:
Chad: Cocktails at a rooftop bar overlooking the city
Jules: Roaming around the city and popping into random dive bars


First impression
Chad: “I thought she was cute and gave off a chill vibe. It seemed like we both just wanted to see what would happen and have an experience.”
“When I first walked in, the manager told me that he’d gotten there half an hour early! I walked over and introduced myself. He seemed on the quiet side but nice.”

Chad: “We had a great conversation. We laughed and talked about our similarities and differences. I got more of a friend vibe than a romantic one.”
“The conversation moved along well, but it was clear we didn’t have much in common. I love travel and he doesn’t…. He said he didn’t see the point.”

Awkward Moment
Chad: “She accidentally spilled red wine on her dress. I asked if she was okay, and she said she was good. But then, replaying the incident in my head, I started to laugh.”
“He asked me if I wanted kids, which kind of took me aback. Then, before I could even answer, he said he hated them. I tried to steer the conversation away from that.”

Chad: “We talked a bit more after dinner, then went our separate ways. There was a moment when I was thinking of asking for her number, but then I didn’t.”
“We left the restaurant and were both like, ‘Hey, thanks for a great time. See you.’ It was casual and cordial, but there was no effort to secure phone numbers.”

Chad: ♥♥♥ “It was great to meet her and get to know her. I didn’t feel a romantic spark, but she was really cool. I had a fun night, and it was cool to meet someone in that way.”
Jules: ♥♥♥ “It was a nice time, no awkward pauses or anything, but that was about it. There wasn’t any chemistry there. I think our sensibilities were different.”

Our daters went to Tuome (536 E 5th St, 646-833-7811)

RECOMMENDED: See more Undateables

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