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Photograph: John Khuu

Dating IRL: Pilsen

Written by
Grace Perry
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Though Chicago's a great place to be single, dating apps can get really exhausting very quickly. You always run into the same types of people, have to gauge whether they actually look like that in real life and have awkward chit-chat as you try to figure out what their "deal" is. We decided to take a break from the app monotony and set up two Chicagoans, Allie and Sean, on a blind date in Pilsen. 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

ALLIE, 27

Financial administrator, traveler and optimist living in Lakeview.

SEAN, 28

Architect, Airbnb host and collector of succulents living in Humboldt Park.

Photo: Erica Gannett

THE DRINKS: Skylark

ALLIE

“I thought he was so cute! Sean was easy to talk to, so I knew it would be a good night. We laughed about how awkward it was to get our photos taken on a first date.”

SEAN

“I talked a bit about the process of renovating my ancient home in Humboldt Park, and Allie seemed interested in the before-and-after photos. For the record, I did spill my drink.”

Photograph: Jaclyn Rivas

THE APPS: Pleasant House Pub

ALLIE

“We started with the usual intro topics—what we do, where we live, what we like about the city—and the conversation took off from there. We split the Scotch egg and bubble cake.”

SEAN

“We both love gin and tonics, and the G&T here arrived in a gigantic goblet. They even included actual juniper berries, which Allie convinced me to eat. I don’t recommend doing that.”

Photograph: Jaclyn Rivas

THE ENTREES: Pleasant House Pub

ALLIE

"I loved Pleasant House. I ordered a pasty that came with a terrific tower of mashed potatoes and gravy on top. We both like to travel, so we talked a lot about our time abroad.”

SEAN

“We spoke about how our parents met and realized our families have quite a bit in common—both of our moms are way older than our dads, and we both have some immigrants in our families.”

THE VERDICT?

ALLIE ♥♥♥♥

“I was definitely a little nervous at first since this was my first time on a blind date, but it ended up being fun. Sean is genuine and a great guy—really easy to talk to and able to joke around.”

SEAN ♥♥♥♥

“I think dating is about opening up a sliver of your personality and seeing what happens, so sometimes it’s hard to determine if there’s an emotional connection after one date. We hang out at similar places, so I hope we cross paths again.”

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