Can not add songs to ipod--says not space when there should be

I have deleted many, many songs from my ipod but when I try to add just one song, I get the message that there is not enough space for the file. Also, the space available is not going down when I delete songs. Help!! Do I need to delete everything and start over?? Many thanks for any help.

Are you deleting actual songs and not just deleting playlists?
Deleting playlists (which are links to the songs) will not free up space on an iPod.

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