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Meet the Undateables: Michael & Theo

Written by
Jillian Anthony

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:
Michael: Can be controlling, and holds his partners to an extremely high standard
Theo: He’s a very specific type, so guys who are into him are few and far between.

Ideal date:
Michael: Picking through the $1 rack at Strand, then walking on the High Line
Theo: A daytime date with food, then an activity like Ping-Pong


First impression
Michael: “My first impression was, I’m going to need a shrink. Theo was just not at all what I was expecting and seemed like a lot of human being. He had a lot of energy.”
Theo: “I was already there, sitting outside, and a guy walked by and I thought, Oh, he’s cute, I hope that’s him. I would definitely have sex with him.  And it was him.”

Michael: “We talked a lot about political and social issues and had similar views on things. But in terms of a romantic or sexual chemistry, there was definitely nothing.”
Theo: “Within five minutes, we knew we weren’t each other’s type. We had a lot in common. He’s a Capricorn and went to art school. He’s into astrology, and he read my sign.”

Awkward Moment
Michael: “The table next to us actually got up and left in the middle of their meal because they didn’t like the service, so that put a little bit of a damper on the conversation.”
Theo: “We had time between courses, so we’d have silent pauses. We were outside, so he’d just look into the street while we sat silently.” 

Michael: “He asked for my Instagram handle, but didn’t throw me a like or a follow later. He got on the train, and I went around the corner to find a homeless person to give leftovers to.”
Theo: “I asked for his Instagram and added him and liked some pics later on, but he never followed me back. I gave him a hug, but our bodies weren’t touching, except our elbows.”

Michael: ♥♥ “The feeling was mutual that we weren’t each other’s cup of tea. He’s a colorful character and a nice guy, and I hope he can find someone who appreciates him.”
Theo: ♥♥♥ "It wasn’t awful, but it wasn’t fun. For gays, we kind of have to be the same size range. Like, if he borrowed my shirt it would be a dress on him.”

Our daters went to Bagatelle (1 Little W 12th St, 212-488-2110)

RECOMMENDED: See more Undateables

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