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Matt and Cara

Each week, we take two New Yorkers who swear they’re totally undateable, and put our matchmaking skills to the test

Will Gleason
Written by
Will Gleason
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Photograph: Ann Sullivan

Why they’re single:
Matt: Since he works long, unpredictable hours, it can be hard to meet someone who is not in the industry.
Cara: She’s been working through her own shit over the past few years.

Ideal date:
Matt: Drinks at a chill bar
Cara: Going apple picking upstate, then hooking up in the orchard

THE DATE

First impression
Matt: “I had to stop at Verizon to get a new phone, so I ended up being a little late. I was attracted to her right away and thought she was really cute and seemed cool.”
Cara: 
“He was about 15 minutes late, which gave me time to try all the rosés on the menu and make friends with everyone at the restaurant. He seemed nice, but he wasn’t my type.”

Chemistry
Matt“I think we had romantic chemistry, on my end at least. We both felt comfortable talking about deep things like past relationships and sexuality, which was nice.” 
Cara: “I didn’t feel any chemistry. Since I teach about sexuality, people often want to talk about sex. We ended up talking a lot about his sexual history.”

Awkward Moment
Matt: “There wasn’t anything too awkward. I guess, if anything, maybe when I was late. I was a little flustered right at the beginning, but the conversation flowed well.”
Cara: “I told the waiter I loved him, and he just said thank you. He was gay, so it wasn’t like I was hitting on him. But for the rest of the meal I was like ‘Wow, you didn’t say it back.’ ”

Afterward
Matt: “We realized it was getting a little late, and we both had a bit of a trek, so we decided to head out. We walked to the train and hugged, and I got her number.”
Cara: “He asked for my number, and I was like, ‘Sure.’ Then we parted ways, and I walked home. He’s texted me since then, but I haven’t texted him back.”

Verdict
Matt: ♥♥♥ “It went really well. I had a lot of fun. She was really cool, and I’d definitely be interested in seeing her again, but I don’t really have any expectations.”
Cara: ♥ “I just don’t always like being the receptacle for someone talking about their sexuality, even though I like that people feel comfortable doing that.”

Our daters went to Ousia (629 W 57th St, Hell's Kitchen)

RECOMMENDED: See more Undateables

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

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