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check out the Viagara triangle (bounded by Rush, State, and Chicago). bunch of restaurants and bars there where the cougars hang out.
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re: gls_junk
Bear in mind that the Viagra Triangle didn't get it's name from cougars. They're a more recent iteration. It's the old guys on the make that give it its true character.
For drinks and apps I (yes, over 35), lean to the wine bars: Webster, Vola, Bin and Bin 36, Randolph Wine Cellar, Pops, etc.
http://chicago.citysearch.com/listing...
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