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Meet the Undateables: Viviana and Emily

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


Why they’re single:
Viviana: She would rather be single than be with the wrong person.
Emily: It’s hard for her to find someone who matches her level of exuberance.

Ideal date:
Viviana: Getting drinks somewhere outside in the sunshine
Emily: A roller disco


First impression
Viviana: “She was very warm and welcoming and high energy. We quickly found out that we have a lot in common and knew a lot of the same people. We’re both in theater.”
“When she walked in, I thought she was beautiful. She came off as smart and very composed. We started talking about [our] professions pretty immediately.”

Viviana: “We didn’t have any romantic chemistry, but I think we were really good at talking to each other and had a friendly night out. The initial spark just wasn’t there.”
“I find I feel romantic attachment very selectively to people, but we were there for two and a half hours—she was so interesting. I probably asked too many questions.”

Awkward Moment
Viviana: “The restaurant didn’t really have any vegan options. They were very accommodating, but by the time I was able to get something vegan, Emily had already finished eating.”
“They bent over backwards to get her a vegan-friendly dish but sent something out with cheese on it, so she had to send it back. The personnel was very nice, though.”

Viviana: “After dinner, we played some games that they had there, like Connect Four and checkers, then left. We hugged outside the restaurant but didn’t exchange numbers.”
“We live in opposite directions so, as the restaurant started to clear out, we went our separate ways. She didn’t ask to exchange numbers, and I was okay with that.”

Viviana: ♥♥♥ “I’d like to connect with her for work stuff and would definitely be friendly with her if I saw her again. She might come to an event that I’m working on.”
Emily: ♥♥♥♥ “I do want to hang out with her again but as friends. I liked hearing what she had to say, and I want to go see her theater company perform.”

Our daters went to Clinton Hall (212-758-8519,

RECOMMENDED: See more Undateables

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