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:
Julia: She's spent the past year getting ready for grad school and finds it hard to find time.
Henry: He ended a serious relationship a year ago and has a hectic work schedule.
Julia: Something that lets her get to know somebody, like drinks and a walk
Henry: Something like that encourages conversation, like drinks and a burlesque performance or comedy show
Julia: "Henry was already at the table and stood up when I walked in, which was nice. There was a third chair, so the first thing I said was, 'Are you expecting someone else?'"
Henry: "We both gave ourselves a look like, Are we on a date? I guess so. Neither of us wanted to be that guy who sat down at the wrong table. She seemed very lively and upbeat."
Julia: "[I didn't feel] romantic chemistry, but he was really easy to talk to. It was fun to get to know him. We talked a lot about our favorite podcasts, current events and politics."
Henry: "We talked about tons, to the point where we kept missing our orders. It's tough to say [if there was romantic chemistry]. It might be a little too early to figure that out."
Julia: "We were both relieved that we weren't matched up with a weirdo. No awkward moments, except maybe at the end. It was sort of like, I guess we should swap numbers."
Henry: "When the conversation went to politics, it made things a little more awkward because that's how politics are right now. Not the sexiest topic. A little more depressing."
Julia: "We walked to the subway, hugged goodbye, swapped numbers. That was it. I'll probably text him. It'll be friendly. I'm not going to be like, 'When can we go out again?'"
Henry: "I walked her to the subway. We exchanged numbers. I haven't been in touch just yet, but possibly in the future. I'm leaving for vacation, but who knows what happens after?"
Julia: ♥♥♥♥ "He was awesome, but I didn't get matched up with my perfect romantic partner so I can't give him a full five stars. If you're down to date a freelancer, he's a great freelancer."
Henry: ♥♥♥♥ "She was very cute and bubbly - very good personality. We talked for about two hours and it didn't seem like that, so that's something. I'm open to [seeing where it goes]."
Our daters went to Mel's Burger Bar (1450 Second Ave. 212-452-1304)
RECOMMENDED: See more Undateables
Want to be set up on a free blind date? Email firstname.lastname@example.org.