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Meet the Undateables: Christina and Anthony

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:
Christina: Likes to be single and loses interest in people quickly
Anthony: Just moved here and has been focused on work

Ideal date:
Christina: A bar for casual drinks and appetizers
Anthony: Start the night at a rooftop bar, and see where it goes


First impression
Christina: “We sat at different chairs at the bar, and he walked up and said, ‘What’s your name? I think I’m supposed to meet you.’ He had nice dimples and a great smile.”
Anthony: “She was very outgoing and not shy at all. She looked like she’d be a fun time. I think she has a pretty face.”

Christina: “I’m definitely more spontaneous and crazy, and the way I live my life, I’m all over the place. He’s definitely more of a planner than I am. ”
Anthony: “We had good conversation, shared some laughs and got to know each other and our backgrounds. I was getting good vibes.”

Awkward Moment
Christina: “We sat next to these people out on their first dinner as a married couple. Here we are on our first date, and you’re showing us wedding photos…”
Anthony: “She doesn’t really hold back. She has a vibrant personality, and we were both pretty good at not incorporating an awkward moment in the conversation.”

Christina: “He offered to walk me home, but I just dropped him at the train, and then he asked for my number. We had a friendly hug and cheek kiss. We haven’t talked since.”
Anthony: “We walked to the train and we separated from there. I took her number down, and that was pretty much it.” 

Christina: ♥♥♥♥ “I had fun. I just felt like he was a little too young for me—I would set him up with a younger friend of mine. It was definitely more of a friendship connection.”
Anthony: ♥♥ “I feel like it was more friendly. I’m not sure if I’d be too interested. She just didn’t really do it for me. But at the end of the day, I had a great time.”

Our daters went to Black Tree BK (261 Metropolitan Ave, Brooklyn, 718-387-7611)

RECOMMENDED: See more Undateables

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