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His weekends are spent tailgating at Soldier Field or the Cell, grilling brats, chops, dogs Your first date: He explains the entire history of Original Six hockey over chicken wings and makes it clear that anyone without a Tony Amonte sweater is a Blackhawks bandwagoner. Your first date: A tour of the Art Institute, followed by drinks at The ature Room, a romantic walk along the lakefront, and a passionate kiss in front of Buckingham Fountain.

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Your first date: Ravinia, of course. Social Media Links. The inevitable breakup: Your worst fear will be confirmed when your best frenemy will send a Snapchat video of him canoodling with a heavily spray-tanned girl at Industry Night at El Hefe.

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The Struggling Comedian Billy, age 41 Neighborhood: Ravenswood He took his first class at iO inand has been trying to make it as a comedian ever since. In his spare time he enjoys homebrewing, rock climbing, and riding his vintage Schwinn bicycle after-hours on the Your first date: A party inside an abandoned warehouse where everyone in attendance seems jaded by abandoned warehouse parties. He dislikes having his 9pm bedtime routine disturbed.

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He lists his union affiliation on his OKCupid profile instead of actual job title -- Union Pipe Fitters Localin case you were wondering. He manages to hold down some sort of corporate job by day, but only because his boss hasn't figured out a way to legally fire him just yet.

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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 into. Your first date : An improv show that you genuinely enjoy Your first date: Painting class at Bottle and Bottega. Say hi to her on Twitter via Chicagoista or DailyUrbanista.

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Your first date: Any beercade in the city you want He has a stable job, owns his own condo, and his Facebook is filled with pictures of his nieces and nephews. From hipsters to douchebags, here are 11 types of single men in the city that nearly every woman will date at least once and hopefully only once in her lifetime.

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