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Meet the Undateables: Emily and Vadim

Jillian Anthony

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:

Emily: She works from home and is in grad school and took a break from dating.

Vadim: His long-term relationship ended three months ago.

Ideal date:

Emily: Drinks that turn into dinner

Vadim: Probably just going to a bar


First impression

Emily: “I got there first and he arrived on time. There was nothing memorable about when we first met. We dove right into ordering before really talking.” 

Vadim: “I got there a bit early and saw her walk in and get seated alone. The host was the most interesting part of the night; he introduced himself and shook my hand.”


Emily: “We covered the basics. It felt a lot more like a business meeting than a date. He was negative about his family right off the bat, which seemed like oversharing.”

Vadim: “I think we established, How bad could it really be if Time Out paid for dinner? So it’s all kind of cynical. I was like, This seems like a normal human being.” 

Awkward Moment

Emily: “He griped a lot about having to travel for work like it was a negative thing. He complained about having to go to Sundance [Film Festival], and I was like, ‘Okay!’ ”

Vadim: “I do a lot of interviews for a living, so if I’m stalled in conversation, I just start asking a lot of questions. We still had to get through this meal.”


Emily: “We had nothing to talk about. The date was so short—like, 45 minutes long. I said I was meeting a friend, and he left. Then I moved to the bar and had another drink.”

Vadim: “She had plans to meet a friend, and I had stuff to do as well. Neither of us was taking this seriously. She said, ‘This wasn’t a horrible date; I’ve had worse.’”

Emily: ♥ “He wasn’t mean or rude or anything, he just had no interest in wanting to get to know me. We said goodbye and both agreed that it could have been worse.”
Vadim: ♥♥  “The whole thing was pretty boring. It wasn’t hostile, it was just meh. She’s a salesperson, and I don’t have that kind of mentality.”

Our daters went to Bar Virage (118 Second Ave, 212-253-0425)

RECOMMENDED: See more Undateables

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