I was riding with a friend from the Midwest last year and he had a number of stories like that. He says that several times a year someone pats him on the shoulder and says, "I lost mine too once. It''s OK, you'll get it back!". And a kid at a stoplight rolled down the car window and asked "Are you poor?" This, to a guy riding a handbuilt custom bike with couplers, dressed in $$ wool cycling clothing, $300 cycling shoes, etc.

You'd never get that kind of question in the Boston area; bikes are common and becoming more so, and additionally there's getting to be a more prominent "cycle chic" culture, too. Even though I'm the sort of gal who has a closet full of identical cargo pants and hasn't worn makeup since the middle school play and think the flowery baskets and accessories are sort of silly, I actually do think that the growth of that particular fashion is a good thing.
When bicycling to work is something commonly done by 30-something professional women who can easily afford cars, care about looking nice and wear nice clothes, and aren't especially sporty/outdoorsy in general, it's less likely that people assume you're poor, childish, drunk, or just a hardcore weirdo for doing it. It means that drivers are less likely to assume that if you're riding in the street it's because you're an idiot with a death wish.