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Festivals There are TONS of street fests, neighborhood fests, food fests and music fests every weekend. Obviously the bigger ones like Taste of Chicago and Lollapalooza will be packed with people, and those kinds of crowds can be intimidating and rage-inducing. It is, however, really easy to start a conversation with a stranger at such events: Go earlier in the day if you want to avoid the really garrulous drunks and lobster tans. And you'd be remiss if you didn't check out the stellar free music and movies in Millennium Park. Who doesn't want to get durrty after watching "Pee Wee's Big Adventure?

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Some dates are a casual party Weekned two, or maybe you even joining a group activity and meeting their friends for the first time. A good place to kick off the first date. On a different note, why not go to a comedy club - its Chicago and practically part of the lifestyle. Being in nature is a great way to turn up the romance.

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