ITunes songs don't play on my iPod

Today I was simply listening to my iPod and I went to a playlist in which all of the songs were ones that I had purchased and downloaded via iTunes. I pressed play, and my iPod simply skipped over all of these songs and would not let me listen to them. This is the 2nd time this has happened, and requires me to connect my iPod to the computer, which may pose problems when traveling. Any suggestions?

It happens to me as well..I use my ipod to go running with and it is really a pain when it skips through the playlist I have created with purchased music or any purchased music.
The only way around it so far is connecting the ipod to the computer before each run...which I sometimes forget at 6am!!!
Advent 3312   Windows XP  

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