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News / Sex & Dating

We set up two Chicagoans on a blind date in River North—here’s what happened

We set up two Chicagoans on a blind date in River North—here’s what happened
Photograph: Jordan Avery

There's no denying that Chicago is a great place to be single, but we could all use a break from the dating-app grind. Enter Dating IRL, an original Time Out Chicago feature that sets up two eligible singles on a blind date at a Chicago hot spot. After a night out, the daters report back with honest feedback on first impressions, chemistry and awkward moments. This time, we matched Jessica and Julius and sent them to Good Measure for dinner and drinks. Let's see how it went. 

RECOMMENDED: Do you want to be set up on a blind date? Apply today.

THE DATERS

JESSICA, 32

Publicist, model/actress and culture geek

JULIUS, 28

Adventurer, photographer and avid reader

FIRST IMPRESSION

JESSICA

“Julius came into the room wearing a smile that put my nerves at ease. He was warm, energetic and funny. He was really present during the conversation.”

JULIUS

“Jessica had a bright smile and good energy. Moreover, she’s funny. She’d been to the bar before, so she gave me the rundown and told me about the fun cocktails.”

Photograph: Jordan Avery

CHEMISTRY

JESSICA

“I was surprised by how well it was going, and that probably made me ‘tune in’ to him even more. There weren’t any dull moments.”

JULIUS

“We had more platonic chemistry, but chemistry all the same, which is more exciting because I think Jessica will be an awesome friend.”

AWKWARD MOMENT

JESSICA

“I had to figure out a way to curb my alcohol intake because I had a flight at 7am the next day. But every time I went to announce my exit, he ordered another drink!”

JULIUS

“I was late to the date because I thought it was late enough to Uber Pool. I was the first pickup and the last drop-off.”

Photograph: Richard Shilkus

THE DATE SPOT: GOOD MEASURE

JESSICA

“The neon lighting is subtly sexy, and the punk-rock music is loud enough that you have to lean in close to hear what your date is saying.”

JULIUS

“Good Measure has well-crafted cocktails and really great service. The bartender was a great conversationalist. I look forward to visiting again.”

THE VERDICT

JESSICA ♥♥♥1/2 (out of 5)

“We didn’t exchange numbers at the end, which is a shame. I would have certainly taken him up on showing me the ropes at a local rock-climbing wall.”

JULIUS ♥♥♥♥♥ (out of 5)

“Jessica and I have similar interests, so it was nice sharing our thoughts on traveling, Chicago and our respective dating experiences.”

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