[title]
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:
Rachel: Doesn't live in the city, hasn't worked in New York for very long and doesn't want to do any online dating
Tim: Has a hard time finding women his age whom he's compatible with, and older women don't want younger guys
Ideal date:
Rachel: Going to an outdoor concert or music festival
Tim: Going to a German beer hall then bowling or to a museum
THE DATE
First impression
Rachel: “He was more formally dressed than I was. He was nice and very polite but not my usual type at all. My type is more alternative and not so preppy.”
Tim: “I was pleasantly surprised that she wasn’t weird looking. She seemed like a normal person who you could walk by on the street any given day. That’s neither good nor bad.”
Chemistry
Rachel: “He’s very interesting, smart and well spoken. He’s different from most people I know. It was a nice, refreshing conversation, but I wouldn’t say it was flirtatious.”
Tim: “We didn’t have a dynamic where I could see us having an in-depth conversation. It was more of a first date, meet-and-greet kind of conversation. I felt platonic toward her.”
Awkward Moment
Rachel: “I felt kind of awkward telling the hostess that I was there for the date. I was just wondering, Do they know this is a blind date? I felt like they knew what was going on.”
Tim: “At the end of the date, I got the hiccups, and I couldn’t really speak in full sentences. It was frustrating. She was lighthearted about it, but I was pretty embarrassed.”
Afterward
Rachel: “He asked if I wanted to exchange numbers. I was fine with that. We hugged—it was a quick, nice-to-meet-you, this-was-a-good-experience kind of thing.”
Tim: “We went to the Princeton Club for a nightcap. I walked her to Grand Central, and she said, ‘Would you like to exchange numbers?’ and put hers in my phone.”
Verdict
Rachel: ♥♥♥♥ “There was nothing bad about the experience. Talking to him was very enjoyable. It just felt more friendly, that’s all. I don’t know if we’ll contact each other again.”
Tim: ♥♥♥ “She didn’t seem driven—for me that’s a big turnoff. Plus, she lives in Westchester. There was no spark to lead me to want a pseudo long-distance relationship."
Our daters went to Kellari Taverna (19 W 44th St, 212-221-0144)
RECOMMENDED: See more Undateables
Want to be set up on a free blind date? Email undateable@timeout.com.