IPod Nano (2nd Gen) wont sync with Itunes 9

I haven't had to sync my iPod for a while, so I think it might be an issue with Itunes 9, but I am not sure.
I have a 2nd gen nano, and itunes recognises it when I plug it in, my iPod display the Do not disconnect thing, but it doesnt sync. I have it set to manually manage music, but that won't make any difference will it? Under "file" the option to Sync Songs on iPod is greyed out.
Does anyone know what to do about this? i'm really annoyed as I do not want to restore my iPod as I have some music on it that I can't find anymore (think it went missing when I moved my library 2 years ago)

i didnt realised iTunes had been changed so you had to physically drag the music you wanted on the iPod onto there yourself.
You don't have to. Only if you want to manually manage the music yourself.
i decided to just automatically sync it, but now it has wiped everything off, and is putting it all back on again! will it do that every time
No.

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