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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:
Jonathan: Has only lived here six months and likes exploring the city more than dating
Derrick: Deep down he’s a Southern belle screaming, “I want the magic!” and he hasn’t found that.
Ideal date:
Jonathan: An early dinner, then walking around Central Park at dusk and looking for fireflies
Derrick: Going to a restaurant for mac and cheese and beer, then dancing, thendollar slices
THE DATE
First impression
Jonathan: “He was really cute and he had tattoos, so that was awesome. He gave me a great smile, and he was very personable with good conversation.”
Derrick: “The first thing that went through my mind was, Time Out New York came through! because he was very handsome. I got the vibe that he was a real gentleman.”
Chemistry
Jonathan: “We talked about everything from childhood to careers. And tattoos. He has two sleeves, and I’m working on a sleeve, so we talked about their meanings.”
Derrick: “We were sitting at the bar and looking at each other, and I was thinking, This is going really awesome, and I would like to kiss him, and he kind of beat me to it.”
Awkward Moment
Jonathan: “The restaurant had a comedy show, so we went in after dinner. A comedian said, ‘Is this Tinder or a Grindr hookup?’ and we just looked at each other and laughed.”
Derrick: “We told the comedians we were on a Time Out New York date, so we were the butt of jokes. They said we looked good together and that we’d be the stars of the magazine.”
Afterward
Jonathan: “We went and had another drink at a bar that he offered to show me. And we exchanged numbers. I’m actually seeing him again tonight.”
Derrick: “I took him to a bar around the corner, and there was karaoke but no country ballads, so we danced. We’ve been chitchatting. We’re meeting up tonight for drinks.”
Verdict
Jonathan: ♥♥♥♥♥ “Just from talking to him, the date was perfect. It was meant for us. He’s super handsome and cute, and he’s a good kisser.”
Derrick: ♥♥♥♥♥ “It was ideal, even if there wasn’t any mac and cheese. He has a really infectious energy, which is what I’m looking for in someone.”
Our daters went to Terra Firma (119 Ingraham St, Brooklyn, 718-366-4375)
RECOMMENDED: See more Undateables
Want to be set up on a free blind date? Email undateable@timeout.com.