I find it amazingly satisfying to cram as much music as possible onto my little bitty nano. Well, not just music, but podcasts and whatnot. Two episodes of day to day (an NPR podcast), the most recent gray's anatomy podcast, and about 500 songs. That is what fits leaving exactly 1.1 of the little bits you can put onto it. I rule. Especially since mine is only a 2gig anyway.
I am on year five of living in Chicago after graduate school. I am planning a wedding. I am a grown up, or I should be. We'll see. That may be debatable.