I just had about the preppiest day in recent memory, but it was nice. What out-of-character-for-you things do you sometimes enjoy?
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Aw man, days like yesterday make me miss DC.
I went to Rock & Roll Karaoke on Monday night at an uber-hipster bar. That was kinda out of character.
for me, i'd have to say it's social clothes shopping at thrift stores.

To wit: met up with an old friend in the morning and stopped by a little french bakery in Georgetown for juice and eclairs, then spent the afternoon bridal dress shopping in various boutiques. Had a sushi lunch in a slightly less stuffy neighborhood, browsed more stores, and ended with dinner and drinks here:
http://www.zoladc.com/
Aside from the sushi lunch, definitely not something I usually do, but it was a rather charming day. :-)