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I have had to do this ALL the time (obviously i'm not good with picking songs) all you have to is right click the song you want to delete and some options should show up on the left or right then click delete or you could drag the song into music off your ipod
make sure on itunes it says sync all selected songs(make sure all songs you want to download are selected)then try to sync it again if thats not your problem it could be a bad i pod
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