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Photographs: Kelsey Dubinsky

Meet the Undateables: Alyssa and Emily

By Ross Tipograph

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.

Photographs: Kelsey Dubinsky

Why they're single:

Alyssa: She has a unique sense of humor and sometimes gets nervous around new people.
Emily: She's picky with personalities and wants someone strong and complementary.

Ideal date:

Alyssa: A movie or dinner before a stroll around the city if the weather is nice
Emily: An amusement park with a pocketful of quarters for rides and games


First impression

Alyssa: “I got there early, and she came on time. Right off the bat, she was very friendly and talkative; she made me feel very comfortable. Conversation started flowing.”
Emily: “She was really cute, which was nicely surprising. I greeted her with a hug while she was seated, so it was a squat hug. We laughed about blind-date awkwardness.”


Alyssa: “I would say it was friendly. We connected over movies and TV shows like Buffy the Vampire Slayer and discussed our past experiences. A lot of good convo topics went around.”
Emily: “We bonded for sure. I don't know if it was romantic; it was more getting to know each other. Some topics took her out of her comfort zone, but it wasn't bad by any means.”

Awkward Moment

Alyssa: “The couple next to us engaged in some heavy PDA. They were just all over each other. At one point, Emily and I thought they were videotaping themselves making out.”
Emily: “There was that super-drunk couple, and I forgot to take out cash for the tip. I was embarrassed, but she said I could make up for it by taking her out another week.”


Alyssa: “It was a friendly goodbye. We exchanged numbers, and she mentioned a bar that has a queer ladies' night. We have plans to hang out, but I'm getting a friend vibe.”
Emily: “The date ended up going for maybe four hours! We walked to the subway, I gave her a quick kiss on the cheek, and I got off the train first. [The kiss] was kind of funny.”


Alyssa: ♥♥♥♥ “It wasn't love, but it was a great experience with her. It was especially great doing something that was so out of my comfort zone.”
Emily: ♥♥♥ “I don't know if it was because of our personality types, but I feel I dominated the conversation a little. Ideally, you have a balance of back and forth.”

Our daters went to Beaubourg (225 Liberty St, 212-981-8589)

RECOMMENDED: See more Undateables

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