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Meet the Undateables: Tara and Brian

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:
Tara: Between working and working out, she doesn’t really have time for anything else.
Brian: He just got out of a long-term relationship.

Ideal date:
Tara: Dinner and drinks, then a walk around the park
Brian: Something in nature, like a hike or the park


First impression
Tara: “I walked in, and I was a little frazzled because I was late, so I started talking, and it automatically just flowed. He was good-looking and seemed like a nice guy.”
Brian: “I got there a little early, and she walked in and we ordered drinks. The first thing I noticed was her accent, because she’s from Staten Island. She seemed really great.”

Tara: “We’re both big fans of Kanye, so we bonded over that. We’re also both into conspiracy theories. We talked about the Mandela Effect, which is proof that time travel exists.”
Brian: “We had great chemistry. We were sitting on opposite ends of the booth, and by the end of the dinner, we were sitting next to each other in the middle.” 

Awkward Moment
Tara: “I’m just kind of awkward to begin with. When I walked in, I rattled off questions. I needed to know everything within the first five minutes, but that’s kind of my personality.”
Brian: “When she arrived, she thought she was really late. She apologized over and over about it. I said, 'It’s okay,' over and over. It was awkward after the fifth time.” 

Tara: “I ordered a car, and he waited outside with me. He said he definitely wanted to see me again and kissed me. We spoke immediately when I got home.”
Brian: “We basically had to end the date early because we both made plans in case the date didn’t go well. We exchanged numbers inside. Outside, I kissed her—twice.”

Tara: ♥♥♥♥ “I think he’s super sweet. I had a great time and would definitely see him again. I’m saving the fifth heart for a date when it won’t be published in print.”
Brian: ♥♥♥♥ “I’m only not giving it five hearts because it would have been great to hang out longer. She was funny and easy to talk to, and we’re planning to hang out soon.”

Our daters went to Delilah (155 Rivington St, 212-777-2520)

RECOMMENDED: See more Undateables

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