Despite being one of the best cities for dating and nightlife in the country, Chicago can sometimes get the best of us. Between long hours on the job, daily commutes and wildly unpredictable weather, "putting yourself out there" isn't always in the cards. That's where we come in. This issue, we played matchmaker in Wicker Park and sent a guy and gal out on a date to three of the bustling neighborhood's hippest spots. The two kicked things off with fancy cocktails at The Violet Hour, headed across the street to Big Star for tacos and ended the night with dessert at Dove's Luncheonette. So, how'd it go? Well, see for yourself.
Do you want to go on a free date? Email datingirl@timeout.com and we'll find you a match!
The daters:
Jordan, 27
Photographer, artist, avid biker and reader; Lincoln Park
Keaton, 25
Barista, saxophonist, drummer and lover of bad jokes; Lakeview
Drinks at The Violet Hour:
Photograph: Sandy Noto
Jordan
“Holy crap, that’s an impressive beard! He was pretty friendly, and we started talking about how we both regretted not biking due to sweat and the fact it might rain, so I immediately thought he was cool.”
Keaton
“This was definitely a different concept for me, so initially it was more like, ‘How weird am I allowed to be?’ It turned out we have a mutual friend, but regardless, Jordan seemed relaxed and friendly.”
Dinner at Big Star:
Photograph: Courtesy Big Star
Jordan
“We were both pretty excited about the tacos. We are very similar people, so it just came naturally. We talked about our mutual fear of vomit and how horrible nosebleeds are…it was great dinner conversation!”
Keaton
“It’s nearly impossible to go wrong with tacos in the mix—so, we may have had some mystical al pastor guidance going on—but Jordan was funny and easy to talk to.”
Dessert at Dove's Luncheonette:
Photograph: Jaclyn Rivas
Jordan
“Neither of us had been to Dove’s before so we didn’t know what to expect. We got ice cream and found out we have a lot in common. We discussed our worst bike injuries, tattoos and music.”
Keaton
“I honestly didn’t know what to expect from this place, but it was nice and low-key. Everything felt natural, and I’m always down with some funky ice cream flavors.”
The verdict:
Jordan: ♥♥♥♥
“Keaton was slightly awkward and hilarious, which is what I look for in a guy. It went well. I can definitely see us being best friends, but I’m not sure about dating.”
Keaton: ♥♥♥♥♥
“The whole night was very chill (for lack of a better word), which is best-case scenario in my book. I don’t think either of us had any expectations going in.”