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Millennium Park in Chicago. Watching people engage Cloud Gate, "The Bean", is sure to give you a smile and a slow shaking of the head from side to side.
Michigan Avenue (Magnificent Mile portion of it) would be second because there's not really any practical place to just sit and watch, or stand out of the way. Although walking up and down the street is not terrible in it's own right, either.
Haven't checked if somebody already mentioned it, but Lake Calhoun, Minneapolis; or Nicollet Ave in downtown Minneapolis (specifically near Target HQ -- whom apparently employs only the most beautiful of people!) are two pretty big hotspots for seeing people and being seen. Others include Lake Harriet, Lake Street (cruisin') and oddly enough, Mall of America or even the Galleria (upscale).
But even if you can hardly walk or hate to exercise, as long as you have a libido and/or marbles rolling around up there, you will enjoy being on Lake Calhoun 8-9 months of the year!
Los Angeles: Hollywood Blvd, Venice Beach...or any beach for that matter, 3rd street Promenade, Olvera st, Fashion district
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