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Moved to the wrong city. Heavy drinking culture in Chicago.
Go to a second city show
Also check out Guthrie's if you're close to the northside - beer and board games
Time for a new girlfroend
Go to Andersonville/wrigleyville. Also check out the theatre scene. Amazing stuff there. Try Lookingglass, Steppenwolf, Goodman or Chicago Shakespeare
Mini golf is always a good time, SO likes to see improv shows
Beercade
California clipper or the tons of jazz bars
Swingers party
You are too young to be asking such questions
Broadway shows!
Lots of stuff in the summer.. but I think things like Adler after Dark (where they keep the planetarium open after hours) and the like are a nice date night type thing if you're into that. And drinking is an option, but not required.
Headquarters - beercade
Let's go to a cabaret show at bordel. I've never been
Wonfun 2fun - it's a really good new Chinese restaurant with a karaoke bar upstairs!