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Meet the Undateables: Kim and Milton

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:
Kim: She knows what she wants and doesn’t want to settle.
Milton: He hasn’t met the right person, and he’s very busy.

Ideal date:
Kim: Grabbing drinks and walking around a fun neighborhood
Milton: Whatever the girl wants to do


First impression
Kim: “The host took me over to meet Milton at the bar. I was so nervous, I have no recollection of our initial contact; I couldn’t tell you if we hugged or kissed or what.”
Milton: “I got there 10 minutes early and ordered a drink at the bar. They introduced me to Kim: She was very cute; I was impressed. We clicked really well and just started talking.”

Kim: “We talked about everything. I think the chemistry was good. We kept acknowledging how funny it was that it was going so well. We talked about a lot.”
Milton: “I was feeling some romantic chemistry. She was very sweet. We were definitely both nervous, but once we got over our initial nerves, we really meshed.”

Awkward Moment
Kim: “When someone cleared his plate, his fork fell onto the booth. It just kind of sat there for a while. But it was going so well—I don’t think either of us acknowledged it.”
Milton: “The most awkward thing, for me, was just not being able to finish my food. I thought I was hungrier than I was, and it just felt kind of awkward that I couldn’t finish.”

Kim: “We left, got another drink, and he walked me to a cab. We kissed—it happened! Then we exchanged numbers. It was a solid first date. We were together for five hours.”
Milton: “We wrapped up dinner, then got drinks at a bar nearby. She told me she went to the same bar before the date and had a pregame drink with a friend.”

Kim: ♥♥ “It was great: good chemistry, easy to talk to. I really respected the way he looked at life and people. He was really respectful—a nice Southern boy.”
Milton: ♥♥ “I’m looking forward to seeing her again. I felt like she seemed interested, but you can never know. It was nice to meet someone so cool in such a bizarre way.”

Our daters went to The Breslin (18 W 29th St, Nomad,

RECOMMENDED: See more Undateables

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