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[title]Frustrated by the dating app struggle? We feel you. That’s why Time Out Chicago is relaunching the Undateables, a series in which we send two eligible singles on a date at some of our favorite Chicago restaurants and bars 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 Sara and Andrew to etta in River North for dinner and drinks—read on to see how it went.
Interested in being set up on a blind date? Apply today by sending an email to undateablechicago@timeout.com.
THE DATERS
Sara is a 26-year-old product designer, rock climber, concertgoer and Ultimate Frisbee player.
Andrew is a 26-year-old project manager, stand-up comedian, indie music fan and pianist.
Why they’re single
Sara: “I think it’s a combination of staying in the same social circles for a while and not meeting very new people, but also not having the desire to be on any apps. I also think I’m kind of selective.”
Andrew: “Between the apps and meeting people organically or meeting friends of friends, it’s just kind of hard to find someone who you connect with and feels like the right match.”
Ideal date
Sara: “I like when you can walk around and look at things and talk, so maybe a museum.”
Andrew: “I usually like to keep things casual—you know, go to a bar, talk over a couple drinks and get to know each other that way.”
THE DATE
First impression
Sara: “He had a nose ring, which was interesting. That was my first thought. It wasn’t a bad thing, but I didn’t expect that. And I never actually found out his age, but I wondered if he was younger than me.”
Andrew: “She was cool. Once we started to get to know each other after the photographer left, we realized we had some stuff in common. We had a lot of similar music tastes, so that was a big plus.”
Chemistry
Sara: “I don’t think there was [romantic chemistry]. I was giving him a good shot, and then I think by 30 minutes in both of us were kind of like, ‘OK.’”
Andrew: “We were kind of getting to know each other, and it didn’t seem like there was much there.”
Awkward moment
Sara: “Talking wasn’t awkward. It felt like talking to a friend. But I don’t think either of us were trying very hard with flirting.”
Andrew: “It really wasn’t too awkward, which was nice. Just to be able to sit down, have dinner and not really feel like there was a lull in the conversation or anything like that.”
Afterward
Sara: “We just said goodbye at the restaurant and left.”
Andrew: “Well, we didn’t know the paying situation—we knew the dinner was covered, but we didn’t know if the waitress knew, and we didn’t want to just bail on the check, so we were trying to flag her down. That was kind of a whole to-do, which was pretty funny. And then after that we just said, ‘Yeah, it was a fun experience, great to meet you’ and went our separate ways.”
Verdict [on a scale of five hearts]
Sara: ♥♥ “We had a lot of similar interests, and nothing was that awkward. He wasn’t exactly my type, but he wasn’t so far out of my type, so everything was set up to be pretty good. But I think we just didn’t click or bounce off of each other well.”
Andrew: ♥♥♥ “I didn’t feel like there was much of a spark or chemistry, but it definitely was a fun experience and I enjoyed getting to know her.”
THE DATE SPOT
Our daters went to etta.
Sara: “I’ve been to etta’s other location before with my parents and thought it was pretty good. The River North location has a bit more of a bougie vibe. But it’s a good spot, very safe—you’re gonna find something you like.”
Andrew: “It was awesome. The food was delicious—I had the calamari rigatoni, which was pretty good. It was a little dark and loud for a first date spot, but it’s definitely a place I would take a third or fourth date for sure.”
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.