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Meet The Undateables: Jenny and Monica

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:
Jenny: She’s generally intimidated and shy around women.
Monica: She’s very timid and doesn’t really click with anyone in her age range.

Ideal date:
Jenny: Meeting at a record shop and then having a cozy listening party
Monica: Having dinner and coffee, then going to a live performance


First impression
Jenny: “At first sight, I thought she was beautiful. I was floored. She seemed bubbly right away but also sophisticated and intelligent, with a great sense of style. I loved her dress.”
Monica: “When I walked into the restaurant, I saw this really cute woman standing at the bar, and the host was like, ‘That’s her!’ I immediately thought she had a warm presence.”

Jenny: “I was definitely attracted to her. I can never tell if a woman is attracted to me, so I don’t know if the physical attraction was reciprocal. But it was there on my side.”
“We both were like, ‘Wow, we really get along well, this is going great.’ If we didn’t have to be places, we probably would have stayed talking at the restaurant even longer.”

Awkward Moment
Jenny: “Honestly, on my part, there was never an awkward moment or awkward pause. There was never one the whole night. She’s so cute, and I have such a crush.”
“I brought up the #metoo movement, then was like, ‘Omigod, that’s a horrible topic for a first date.’ But she told me she’d put together a display on it at work.”

Jenny: “We were there almost three hours, then headed out and hugged goodbye. I woke up to a text from her about an actress’s name that we couldn’t think of.”
“We exchanged numbers and were going to go to the subway station together, except the train had stopped running. So we waited together for an Uber and a taxi.”

Jenny: ♥♥♥♥ “I was smitten. I don’t want her to think I’m a stalker, but I was so happy that we connected and had shared interests. We’ve discussed going on another date.”
Monica: ♥♥♥♥♥ “It went really well. It actually made me excited instead of just kind of thinking, Oh, this is fine. I’d honestly be excited to see her again.”

Our daters went to Alice's Arbor (459 Classon Ave, 718-399-3003)

RECOMMENDED: See more Undateables

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