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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:
Hannah: Is independent and thinks dating should be easy, so as soon as something stops being fun, she wants to be done
Ryan: Has moved around a lot and been focused on his career, so is just starting to get back into the dating scene
Ideal date:
Hannah: Summer drinks on a rooftop with a beautiful view
Ryan: A bottle of rosé in Central Park during the summer, with blankets, food and games
First impression
Hannah: “I thought he was cute. He was really nice and not scary—with a blind date, you never know. I noticed his cologne right away. It smelled very nice. And I liked his haircut.”
Ryan: “She got there earlier, so she was at the bar. She seemed a little quiet and shy. I go for more outgoing, so she wasn’t exactly my type, but she was a very nice girl.”
Chemistry
Hannah: “I don’t think I have a type, but I also don’t think he was my type. The conversation flowed—no awkward pauses—but it wasn’t deep, involved or all that interesting.”
Ryan: “We talked about usual first-date stuff—where we’re from, what we do. We had good conversation for a while, but toward the end, we kind of ran out of things to talk about.”
Awkward Moment
Hannah: “After we paid, he was like, ‘So what are your passions?’ It was a weird time to ask a deep question. I was ready to go, so I ended up giving kind of a flippant answer.”
Ryan: “When we met, the hostess brought me to where she was waiting but didn’t introduce us. I was just kind of standing there and had to say, ‘Hi, I’m assuming you’re Hannah.’”
Afterward
Hannah: “We walked out and he was like, ‘I should take your number so we can find out how this all plays out.’ I wasn’t going to offer it or ask for his, but I was fine to give it.”
Ryan: “I ordered a second drink but noticed she was kind of ready to go. We did a little friendly hug, nothing romantic. I got her number—I felt like it would be rude if I didn’t.”
Verdict
Hannah: ♥♥♥ “It was a fun night out with a really nice guy who I would never have met otherwise, but I don’t think I need to see him again. There was no romantic spark.”
Ryan: ♥♥♥ “It was a good time. The food was really good; the date was okay. She’s not somebody who I would go on another date with. She’s a little bit too reserved.”
Our daters went to The Gander (15 W 18th St, 212-229-9500)
RECOMMENDED: See more Undateables
Want to be set up on a free blind date? Email undateable@timeout.com.