I can get iTunes to shuffle a playlist while playing on my computer, but the ipod itself won't shuffle it. As Ponine said, you can manually shuffle the playlist order before putting on your ipod, but it will remain in that order on your ipod.
It's one of my 2 biggest complaints about iTunes/iPod (the other being that plugging your ipod into your computer via USB resets the "shuffle" every time).
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'He who receives an idea from me, receives instruction himself without lessening mine; as he who lights his taper at mine, receives light without darkening me.'
-TJ
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