You can remove individual songs, audiobooks, and videos from your iPod. Removing an item from your iPod does not delete it from your iTunes library.
To remove items from an iPod other than an iPod shuffle, first make sure that iTunes is set up to manually manage items.
To remove songs from your iPod:
Connect your iPod to your computer.
When the iPod icon appears in iTunes, select it.
If the disclosure triangle to the left of your iPod is closed, click it so that you can see the iPod contents.
Select the item you want to delete and press the Delete key.