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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

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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