Reading this made me realize an implied feature of the iPhone - with an 802.11 connection and running OSX, this could essentially run iTunes. Well, when I open iTunes on my laptop on campus I see a dozen or so shared music lists on the network. If you want to share your music with the cute girl in the coffee shop it would be easy as pie with an iPhone - as long as you're on the same network. This scheme would work better than the Zune's squirt anyway. You can stream the music from someone else's machine as long as they are in range for as many times as you would like, and when you're no longer on the same network it goes away (iTunes doesn't allow you to copy the music over). Plus you get the added benefit of searching the other person's music list and you can share passively. The iPhone just might be a lot more social.