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 Lauren and Prabu to Tack Room in Pilsen for dinner and live music—read on to see how it went.
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Lauren is a 40-year-old teacher, voracious reader, sci-fi enthusiast and lover of BBC.
Prabu is a 42-year-old software developer, foodie, traveler and jungle music fan.
Why they’re single
Lauren: She hasn’t been actively dating since the pandemic.
Prabu: He spent his earlier years focused on his career and has struggled to find someone who shares his interests on dating apps.
Lauren: Dinner and then a play or musical, with a stop at a café afterwards to discuss.
Prabu: Getting to make a real connection with someone.
Lauren: “He’s a very amiable individual. When I walked in, he seemed scared, so I called his name. You know, ‘Prabu! Hello!’ I don’t think he knew who I was. But then I thought immediately that maybe I’m overdressed.”
Prabu: “She was great. She had a beautiful smile and smelled nice. And she was very easy to talk to—she just seems like a really great person.”
Lauren: “He’s definitely someone who would be No. 1 on my friends list, like he’s someone who could be a really good friend. I see no romantic involvement whatsoever. ... I wouldn’t say we had much in common, but we had continuous conversation throughout the night, which was great.”
Prabu: “It felt in the beginning [that there could be romantic chemistry], but that declined a bit as we talked more. Like, it was my first time going to a piano bar, but I think she had been to one before and she knew all the songs they were playing. I mean, I had kind of heard of them, but she knew all the words to them—Rod Stewart, Billy Joel—and she was singing along to them. ... Then they played a Smashing Pumpkins song, and I’m like, ‘Oh, that’s a song I grew up listening to.’ And she was like, ‘Who are they?’ ... But it’s not just that one little thing, it was a combination.”
Lauren: “I think the posing was kind of awkward. Immediately we had to get close and smile—and that was kind of hilarious, actually.”
Prabu: “I knew a photographer was going to be there, but I thought they were going to be candid shots, and then she was having us do poses and stuff. I was a little out of my element, I guess. But it was twofold, because [the photographer] brought us closer together, and it kind of broke the ice, which was awesome.”
Lauren: “We left a little bit after 9:30 and he walked me to my car. I was parked very close—on the same block, actually—so I was maybe three feet away from Tack Room. He was farther away, so I told him to go ahead. We hugged and said goodbye.”
Prabu: “As a reflex I said I’d walk her to her car, even though I guess it was still daylight and there were lots of people there. But then as soon as we walked out she was like, ‘Oh, my car’s right there.’ ... We just hugged and said, ‘Nice meeting you’ or something like that. But we didn’t get each other’s numbers or anything.’
Verdict [on a scale of five hearts]
Lauren: ♥♥ “I talked to my best friend when I got in the car. And I specifically said, ‘He would definitely be in the friend zone.’ ... I had a fun time, even though I was not interested in Prabu romantically. He would definitely be a fun friend to hang out with, and I have plenty of those—plenty of male friends included.”
Prabu: ♥♥♥♥ “I would say three and a half or four. It wasn’t a bad date, but it wasn’t a date where I would want to continue seeing her.’
THE DATE SPOT
Our daters went to Tack Room.
Lauren: ‘I definitely enjoy piano music, so I enjoyed seeing a piano bar. ... The musician was really great, and I knew a lot of the songs he was performing. Prabu kept trying to encourage me to sing a duet, and that was hilarious.”
Prabu: “I’d never been there, but yeah, it’s a good place. I had the shrimp cocktail and a burger—I’d recommend it.”
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.