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:
Lisa: She’s looking for a guy who can keep up but is just finding boys in men’s clothing.
David: He takes a while to open up, which is hard in the fast-paced age of Tinder.
Lisa: A low-pressure meet-up, like coffee that could turn into lunch
David: A chill activity, like a walk to the Tompkins Square Dog Run
Lisa: “I got there early, so they seated me. Since I’m a hairstylist, it’s hard for me to date a bald guy. He’s a little bit shorter than me, but the hair thing was like, ‘Aw, man.’”
David: “Lisa has a big, gorgeous smile, and she’s super friendly, but the host was there when I met her, so I didn’t get to say hello fully on my own terms.”
Lisa: “He seemed cool until we ordered food, and he turned really indecisive. I have a dominant personality, so the guy has to be doubly dominant.”
David: “We got along well, but it became clear this wasn’t a love connection. When she mentioned astrology the third time, it was a little hard for me to connect.”
Lisa: “I showed him an inspirational quote on my phone, and he swiped and saw a picture of a sleeping guy. That’s why I hate when people look at my phone.”
David: “She asked my sign. I invited her to guess, she guessed wrong, and I teased her about it. I finally told her, and she talked about how great that was.”
Lisa: "I had to pick up my dog, so I was moving things along. He was asking me what I was doing over the weekend, but we didn’t exchange numbers. A cab came and I jumped in.”
David: “I don’t think either of us were heading in the direction of continuing. I walked her out, and she hailed a cab. I said, ‘Thank you for sharing this adventure with me.’”
Lisa: ♥♥♥ “He probably would’ve been cool as a friend, but what’s the use of another guy friend? He was cool to talk to, but I would’ve devoured him.”
David: ♥♥♥ “It was nice for what it was. Dating in New York is hard. It’s just so easy to meet people that I think our thresholds are higher for who we are interested in.”
Our daters went to Le Coq Rico (30 E 20th St, 212-267-7426)
RECOMMENDED: See more Undateables
Want to be set up on a free blind date? Email firstname.lastname@example.org.