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Meet the Undateables: Kait and Jon

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:
Kait: She’s not willing to give up her free time unless there’s a real connection.
Jon: A past relationship has made it difficult for him to open up.

Ideal date:
Kait: Going to a weird cultural event and then drinks
Jon: Drinks and then seeing a comedy show


First impression
Kait: “I got there right before him, and we met at the bar. I thought he was cute, and then we sat down at the table. He was really funny and also seemed genuine and warm.”
Jon: “I had booked it down from work, so I was a little sweatier than I wanted to be. I was nervous, but she was great. We hit it off quickly, and she was really cute.”

Kait: “We figured out we both play soccer in the city. He’s going to the World Cup this summer, and I’m obsessed with soccer. It felt like we became friends right away.”
Jon: “I would say there was chemistry, particularly by the end. Our table looked out on the Empire State Building, and she said she’d never been to the top, so we decided to go.”

Awkward Moment
Kait: “We got one more round of drinks and then walked over. They take a picture of you before you go up, and we just kind of stood side by side. We didn’t know what to do.”
Jon: “When we were at the top, the view was amazing, and I was like, ‘Is this too cliché to kiss you? Is it weird?’ But she was into it. It was just such a fantastical situation.”

Kait: “After that, we talked for a few more minutes, but we were both freezing, so we went back down and said goodbye on the sidewalk. He asked for my number.”
Jon: “We went back down and stopped by the photo booth to see our pic. Then we exchanged numbers and left. We met up again that Sunday to play soccer.”

Kait: ♥♥♥♥ “It was a really fun date. I’d love to hang out with him again, maybe play some more soccer—maybe steal his tickets to the World Cup.”
Jon: ♥♥♥♥♥ “She was really cool—we vibed pretty quickly. She had one of those up-for-anything attitudes that I like in anyone, friends or romantic partners.”

Our daters went to Spyglass Rooftop Bar (212-730-0538, 47 W 38th St)

RECOMMENDED: See more Undateables

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