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Meet The Undateables: Madeline and Chris

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.

Photograph: Kelsey Dubinsky

Why they're single:

Madeline: She can’t find time for dates between work and traveling.
Chris: He’s been city-hopping for work and hasn’t had time to settle down.

Ideal date:

Madeline: Drinks or something interactive so you can keep things going if the chemistry is right
Chris: Something fun and active that puts no pressure on the conversation, like rock climbing


First impression

Madeline: "I got there before he did by a few minutes, so it wasn’t too long of a wait. I thought he looked like a cool guy. It was a really casual hello—like I was meeting a friend."
Chris: "
She arrived a little early, which was a good sign. She was very friendly, personable and cool. We bonded and ordered a huge sampler of many different plates of food."


Madeline: "We were there for a good three hours. I didn’t feel it was romantic, but we did have a lot in common: We were interested in each other’s jobs, and we both do improv."
Chris: "
Conversation didn’t get too deep: ‘What do you do for work?’ ‘What do you do for fun?’ It was more on the friendship side. There wasn’t really a romantic spark."

Awkward Moment

Madeline: "They put us in this back room that was a little quieter; it felt more private than the main restaurant. But it wasn’t just us; there were like three tables."
Chris: "
We were immediately greeted by the chef and the manager. Also, our hobbies didn’t necessarily sync up: I’m more sporty; she has other interests."


Madeline: "We walked together for a few blocks, said goodbye, and that was it. No number exchange or anything. There wasn’t enough attraction for me to feel the need to see him again."
Chris: "
We left the restaurant, walked to the subway together, hugged goodbye and parted ways. We walked far before splitting up, then we said, 'Thanks for the fun night.'"


Madeline: ♥♥♥ "It felt casual from the beginning, honestly. It was 100 percent friendly. It was a nice night, but obviously I have no romantic inclinations about it."
Chris: ♥♥ "She’s a great girl, great conversationalist and a great catch for someone else. She was very entertaining and fun, just not exactly my type."

Our daters went to SakaMai (157 Ludlow St, 646-590-0684)

RECOMMENDED: See more Undateables

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