Error message - what has the boy done now?

My son deleted his playlist on iTunes on Saturday for some unknown reason. Today he plugged in his iPod and all the songs on it deleted/erased.
So I thought, just create a new playlist right? Yet after multiple tries, I get a message saying that the iPod cannot be synced because all playlists selected for updating no longer exist.
I am so confused. What step am I missing or foregtting?

See this user tip.
http://discussions.apple.com/thread.jspa?messageID=607312&#607312
For versions of iTunes from 7 onwards, the option to "update selected playlists" is now under the "music" tab in the summary screen.

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Error message - what has the boy done now?

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