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We sent two Chicagoans on a blind date in Wicker Park—here’s how it went

We sent two Chicagoans on a blind date in Wicker Park—here’s how it went
Photograph: Sarah Joyce

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, each dater reports back with honest feedback on first impressions, chemistry and awkward moments. This time, we matched Raphael and Jessica and sent them to etta in Wicker Park for dinner and drinks. Let's see how it went.

RECOMMENDED: Want Time Out editors to set you up on a blind date? Apply for Dating IRL today. 

Photograph: Sarah Joyce

MEET THE DATERS

RAPHAEL, 27: Extrovert, music lover, creative

JESSICA, 24: Social media manager, book nerd, feminist

Photograph: Sarah Joyce

FIRST IMPRESSION

RAPHAEL

Jessica was the perfect person to ease the awkwardness of a blind first date: all smiles, cute, nice and just as open to trying new things as I am.”

JESSICA

I usually go for shy, clean-cut guys, so his tattoos and extroverted personality were off-brand for me. But the conversation flowed smoothly, so maybe I should reconsider my type." 

Photograph: Sarah Joyce

CHEMISTRY

RAPHAEL

It was really easy to talk to her right from the get-go, and although there weren’t fireworks, I definitely wouldn’t put our connection entirely in the ‘friend’ bucket.

JESSICA

There was definitely a spark, but I’m not sure if it was first-date excitement or actual chemistry. I’m thinking it’ll end up more of a platonic thing, but I’d like to feel it out.”

Photograph: Sarah Joyce

AWKWARD MOMENT

RAPHAEL

There weren’t many awkward moments, which is rare for a first date. That being said, a few patrons gave us interesting looks, and someone asked if we were famous.”

JESSICA

I was worried our conversations would feel forced, but it felt pretty natural. Our server knew we were on a blind date and joined us for dessert: coffee-infused tequila!

Photograph: Jaclyn Rivas

THE DATE SPOT: etta

RAPHAEL

Everything we tried was great, the ambience was solid, and the service was exceptional. The bubbling shrimp and roasted asparagus were fantastic.

JESSICA

Everything we had was incredible, from the cocktails to the appetizers and entrées to the coffee-infused tequila for dessert. I’ll definitely be back.”

THE VERDICT

RAPHAEL ♥♥♥♥ (out of 5)

We had some things in common, but I think she’ll find someone that fits her style far more than I do. She was really nice, but I’d rather not waste her time.

JESSICA ♥♥♥♥ (out of 5)

Now that we got the first-date basics out of the way, I’m curious to see if discussions flow as easily. I don’t think he’s my soul mate, but we had a great time.

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