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[title]Frustrated by the dating app struggle? We feel you. That’s why Time Out Los Angeles is launching the Undateables, a series in which we send two eligible singles on a date at some of our favorite local spots in the hopes of striking up a new spark. Following the night out, the daters report back with their candid thoughts on first impressions, chemistry and (of course) the inevitable awkward moments. This time, we sent Kelly and Jimmy to the Rooftop at the Wayfarer Downtown L.A.—read on to see how it went.
THE DATERS
Kelly is a 28-year-old IRS agent.
Jimmy is a 29-year-old software engineer.
Why they’re single:
Kelly: She says she’s a hopeless romantic who hasn’t met someone worth pursuing yet.
Jimmy: He says he’s prioritized school and starting his career over a serious relationship.
Ideal date:
Kelly: A picnic or stargazing filled with conversation, jokes and banter.
Jimmy: Anything that’s super fun where he can enjoy himself.
THE DATE
First impression
Kelly: “He seemed shy, quiet and reserved. But I interview people for a living, so for me it’s really easy to get people talking once you ask certain who, what, where, why questions.”
Jimmy: “I thought she was super nice and really easy to talk to. I was a little bit surprised that we basically went to college in the same city.”
Chemistry
Kelly: “We found out that we both went to undergrad in Amherst, Massachusetts, so we kind of reminisced about our undergrad days. He was really easy to talk to—unintimidating and calming—but I didn’t feel that much romantic attraction.”
Jimmy: “We talked about the East Coast to West Coast transition (for her), and hobbies, interests and career stuff. I don’t think we ran out of stuff to talk about, but I would say that it was kind of awkward at times.”
Awkward moment
Kelly: “Nothing in particular. I think near the end of the date the conversation kind of died down—I was getting a little food coma because the food was amazing.”
Jimmy: “I mean, I didn’t know her at all and she didn’t know me, so it was kind of weird to try to find stuff to talk about, I guess.”
Afterward
Kelly: “We shared a dessert and then walked to the parking lot together. He asked for my number to keep in touch, so I was pleasantly surprised about that because I kind of felt like I was initiating and leading most of the date.”
Jimmy: “I’d definitely be interested in talking to her again and hanging out. I feel like I didn’t get to know her that well.”
Verdict [On a scale of five hearts]
Kelly: ♥♥♥ “It was a very chill date, it felt like two old friends catching up. But I would give it a second go; I usually don’t write anyone off on the first date because I know how nerve-racking it can be.”
Jimmy: ♥♥♥♥ “It was a really nice evening and I really enjoyed it. I’d be interested in chatting some more and going out again.”
THE DATE SPOT
Our daters went to the Rooftop at the Wayfarer Downtown L.A.
Kelly: “The restaurant was so good. I was amazed at the view; it was the perfect time at sunset. The server was so friendly, so funny. I got the steak—it was amazing, they cooked it perfectly—and then the beignets for dessert were so good, they made them fresh.”
Jimmy: “I thought the restaurant was very good, the food was good. We arrived just when the sun was setting and sat on a corner table—it was kind of like a scene out of a rom-com.”
Maybelline Fit Me foundation was provided to Undateable participants along with concealer, powder and blush. Visit the Fit Me foundation match finder to find the perfect shade for you to wear on your next date.