This is how to delete songs manually from your iPod…

Connect it to your computer and make sure iTunes is open on your computer. Click on your iPod's name under ’Devices’ on the left hand side of the iTunes interface.

Click on the 'Summary' tab. Under 'Options' make sure you've checked the 'Manually manage music' check box. Under ’Devices’, select 'Music' and select a song you want to delete and press the 'delete' key on your keyboard.

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To delete all songs, go to 'Edit > Select All' and hit the 'Delete' key.

Note: When you delete a song or other item manually from your iPod, the song is not deleted from your iTunes library. To delete a song from the iTunes music library, click on 'Music' under 'Library', select a song and hit the delete key on your keyboard.