Purchased songs show up, but won't play on iPod

Hey-newbie here. I checked out iPod 101 and it doesn't address this exact problem (or if it does, I'm thick and can't see it!).
I bought some songs off iTunes. They show up in the Purchased file and in the Library. They also show up on the iPod, but when I got to play them, they skip to the next song. I've restored, deauthorized and reauthorized, turned off virus protection-what am I missing? The iPod is one week old! Arrgh! TIA.

Don't have a solution, sorry for that; but you wouldn't happen to be Tia Ann would you?

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