after a certain amount of time your iPod will require a resync to update license, if you delete the songs you may need to repurchase them. I am not entirely sure but if you change the settings on your ipod so that you update it manually rather than syncing it you might be able to delete them. well first sync it once then change your iTunes setting so that it doesn't automatically sync songs when you connect your ipod then delete your songs of your computer
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delete the one on your ipod then (from your library) simply drag it back to your ipod
The music files should still be in your "My Music" folder.
In Itunes itself, just press the delete key. If you want to delete from the iPod itself, call up the contents when it is plugged in, highlight (by clicking) what you want to delete, then press the delete key. Alternatively, just delete it from Itunes then sync your iPod - it will cope exactly what is in iTunes.
itunes error 13010 refers to a corrupt itunes library genius file -- to resolve it remove the "itunes library genius.itdb" from your itunes folder and relaunch iTunes
go on itunes (make shore its plugged in) and then go to sync,music then untick the song and it wont be on ipod or delete the song from ur library! plz reccomend...im new here