Let’s get real: App dating sucks. Navigating the world of online dating is exhausting, tedious, and too-often unsuccessful. You always meet the same kinds of people on Tinder, grab beers, tip-toe through awkward conversation and try to feel out whether this is going anywhere. So we decided to take a break from the app monotony and set up two Chicagoans, Sam and Amy, on a blind date in Bridgeport. Let’s see how it went.
Do you want to go on a free date? Email datingIRL@timeout.com and we might set you up with a match!
Photograph: John Khuu
THE DATERS
Amy, 25
Advertising account planner, wannabe chef and cofounder of a brewery-of-the-month club living in East Village
Sam, 24
Video producer, football fanatic and improv nerd living in North Center
Photograph: John Khuu
THE FUN: Bridgeport Art Center
AMY
“I’d definitely recommend Bridgeport Art Center, but it doesn’t offer much by way of an icebreaker. Thankfully, we were both pretty talkative, so it wasn’t awkward at all!”
SAM
“We tried to sneak into a wedding on the floor above us. But we then made eye contact with the bride down a long hallway. We got scared and said, ‘Let’s go drink.’ ”
Photograph: Jaclyn Rivas
THE DRINKS: Maria's Packaged Goods & Community Bar
AMY
“Maria’s is an awesome space with a different vibe in each room. We talked about everything from family to bad date experiences, comedy, favorite movies—even politics.”
SAM
“At one point, a very drunk man sat down next to us. He said he couldn’t resist talking to us because of how nice we looked. He’s going to be the best man at our wedding.”
Photograph: Jaclyn Rivas
THE MEAL: Kimski
AMY
“Polish and Korean fusion is fabulous. Who knew? We shared a bunch of things, and they were all delicious, but the poutine… oh, my! It was melt-in-your-mouth goodness, with cheese curds and spicy kimchi on top.”
SAM
“Things were going so well that, after dinner, we kept things going and caught an improv show. I think the entire date lasted, like, seven hours or something!”
THE VERDICT?
AMY ♥♥♥♥
“The date was a blast! Sam is in an improv group and performs at the iO Theater, so we continued the date and went out to see a comedy show after dinner.”
SAM ♥♥♥♥
“I’d love to see her again. She was so intelligent, charming, charismatic and, of course, beautiful. It was one of the best dates I’ve been on.”
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