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Michael and Kyle

Each week, we take two New Yorkers who swear they’re totally undateable, and put our matchmaking skills to the test

By Will Gleason

7-Eleven App

Photographs: Ann Sullivan

Why they’re single:
Michael: It’s impossible to find a gay guy in New York who wants to be monogamous.
Kyle: He’s self-proclaimed “super extra.”

Ideal date:
Michael: Drinks and then a stroll around the city
Kyle: A walk through Central Park—so if it goes wrong, he can just run away


First impression
Michael: “They seated us outside, and my first impression was that he had very strong cheekbones, big eyes and that he was very skinny. He was friendly and maybe a bit nervous.”
Kyle: “I thought he was very attractive. What I find most attractive in anyone—and what I found in him—is a certain amount of self-confidence and self-awareness.”

Michael“There wasn’t really any romantic chemistry. He wasn’t really my type, but I can make conversation with pretty much everyone. I think that was pretty reciprocal.”
Kyle: “It’s kind of hard to tell on a first date, but I feel like there could be a really strong friendship there. Maybe there’d be more romantic chemistry if we got to know each other.”

Awkward Moment
Michael: “I made a Clueless reference, and it was just totally lost on him. Have to say, if someone doesn’t like Clueless, that’s kind of a deal breaker for me.”
Kyle: “I told him I’m vegan, just because of health reasons. He kind of paused for a second and then asked me if he could still get the burger. I was like, ‘Yes! That’s fine!’ ”

Michael: “He started yawning around 10:30, so we exchanged numbers and Instagrams. For some reason, he didn’t follow back. Then we hugged, and he hopped in his car.”
Kyle: “The most fun moment of the night was after we both got up from the table. We weren’t so intensely staring at each other’s eyes then, and it didn’t seem as intimidating.”

Michael: ♥♥♥ “Not really any physical chemistry, but fun conversation. He’s a very interesting guy, and I definitely appreciated that he was in a creative field like me.”
Kyle: ♥♥♥ “He was very nice. It was better than I was expecting it to be. And at the very least, I hope that I get a good friend out of the experience.”

Our daters went to Clinton Hall at the Pod Brooklyn (247 Metropolitan Ave, Williamsburg)

RECOMMENDED: See more Undateables

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Top of the Empire State Building

Attractions Monuments and memorials Midtown West

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Jane's Carousel
Photograph: Lee Magill

Jane's Carousel

Attractions Arcades and amusements DUMBO

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Grand Central Terminal
Photograph: Jeffrey Gurwin

Grand Central Terminal

Attractions Historic buildings and sites Midtown East
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The Jacques Marchais Museum of Tibetan Art
Photograph: courtesy Jacques Marchais Museum of Tibetan Art

Jacques Marchais Museum of Tibetan Art

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Photograph: Courtesy Creative Commons/Flickr/David Ohmer

Bow Bridge at Central Park

Attractions Parks and gardens Central Park

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Photograph: Shutterstock

The Lincoln Center fountain

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50 free events, Stargazing, The High Line
Photograph: Courtesy Liz Ligon/Friends of the High Line

The High Line

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