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Over 50? His response: Gregory, age 35 Neighborhood: He dislikes having his 9pm bedtime routine disturbed. Ravinia, of course.

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Wes, age 36 Neighborhood: Fifty percent of your date will be spent sitting with an awkward smile plastered on your face while he catches up with everyone he bumps. Your worst fear will be confirmed when your best frenemy will send a Snapchat video of chocago canoodling with a heavily spray-tanned single guys in chicago at Industry Night at El Hefe. Hector, age 28 Neighborhood: Bears, Hawks, Sox, Bulls.

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An improv show that you genuinely enjoy Jeff, age 26 Neighborhood: Painting class at Bottle and Bottega.

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The Insufferable Hipster. The Native Chicagoan Mikey, age 27 Neighborhood: The Temporary Resident Antoine, age 27 Neighborhood: The Industry Guy Wes, age 36 Neighborhood: