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:
Steph: She finds dating apps way too depressing and overwhelming.
Alex: He’s the pickiest guy of all time.
Steph: Picking a random subway stop and exploring a neighborhood
Alex: Reenacting the first verse of “Mind Sex” by Dead Prez but without the drugs
Steph: “When I got there, he was already seated. He was a talkative and confident guy. It wasn’t weird to meet him or anything. He was cool and friendly and warm.”
Alex: “Right off the bat I could tell she wasn’t my type physically. But she was friendly and seemed like a good listener, so I was hoping we’d have a nice conversation.”
Steph: “We pretty much talked the entire time. I didn’t think he wasn’t attractive, but it felt a lot more casual than I thought it would be. It was almost like a job interview.”
Alex: “She said I looked like Ray from Girls, so I didn’t think she was really into it, since he’s not that attractive. It was a very casual vibe, no flirting in the slightest.”
Steph: “I told him he looked like Ray from Girls, and he did not take that as a compliment. But it should be said that I think Ray is attractive. I didn’t think that was an insult.”
Alex: “We were talking about how we hated the rain, and when I told her I’m from Puerto Rico, she asked me if the weather there was warm. I was like, ‘Do you even geography, bro?’ ”
Steph: “We stayed for dessert and then went outside in the terrible weather. We said goodbye and hugged. Then I almost hit him in the face with my umbrella.”
Alex: “We said goodbye outside the restaurant, but we had our umbrellas out, and when I went in to give her a hug, she almost poked my eye out.”
Steph: ♥♥♥ “It wasn’t terrible! I didn’t hate him, and he seemed like a nice dude. We had a good time for not knowing anything about each other.”
Alex: ♥♥♥ “We had a lot in common, and I really enjoyed myself. We both like food; we both majored in journalism. But there wasn’t a romantic vibe.”
Our daters went to Megu at Dream Downtown (355 W 16th St, 212-885-9400)
RECOMMENDED: See more Undateables
Want to be set up on a free blind date? Email firstname.lastname@example.org.