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Meet the Undateables: Sara and Alyssa

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:
Sara: She works and goes to school full-time, so she’s really busy.
Alyssa: She just got out of a seven-year relationship in May.

Ideal date:
Sara: An active date like rock climbing or ice-skating in Central Park
Alyssa: Hitting up a good dive bar with a questionable health-code rating


First impression
Sara: “I got there first. She was about 10 minutes late but very apologetic about it. I thought she was attractive and nice. She sat down, and we started talking right away.”
“I was late, but she was super understanding. She was the complete opposite of my type, but I was still intrigued. She was also really friendly right off the bat.”

Sara: “She was fun to talk to. We actually ended up talking for three hours. But she did just get out of a long-term relationship, and I could tell she was dating around a bit.”
“I got more of a friend vibe, but the night was great. It made me think about how many people in the past I may have passed up just because they weren’t my type.”

Awkward Moment
Sara: “When I first got there, some random guy dropped a beer on me, so that was awesome. It shattered on the floor and got all over my pants. I don’t think he even noticed.”
“Apparently, the waitstaff told [Sara] to signal if the date wasn’t going well. I kept looking over and saw them staring at us, so that was kind of awkward.”

Sara: “I had to get up at 4am the next day, so we decided to head out. I gave her my number and we hugged. I’m not very touchy-feely, so a hug from me is pretty good.”
“When we were outside, we were joking about people who go on dates and have completely different ideas of how it went. But we both had a good time.”

Sara: ♥♥♥♥ “It was fun, but I could tell she wasn’t really ready to date someone. It sounds like she’s going out on
a lot of dates.”
Alyssa: ♥♥♥♥ “It wasn’t what I was expecting, but it was a welcome surprise. It was my first real blind date and could have gone terribly, but it went well! I’d see her again.”

Our daters went to Treadwell Park (301 South End Ave, 212-945-0528)

RECOMMENDED: See more Undateables

Want to be set up on a free blind date? Email

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