Unable To Sync Ipod. Help?

I have my iPod plugged into my computer, and it is registering on iTunes, but everytime I click the Sync button on iTunes, the letters turn grey like they do when you've clicked it, but then they turn black again and it does not sync my iPod.
My friend had just recently put some music on my iPod from his computer, would this have affected it?

Well, I unchecked the Manually Manage Music and Video box and it synced my ipod but took off the songs my friend put on there. Oh well, Ill have to get them again.

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    Well, I unchecked the Manually Manage Music and Video box and it synced my ipod but took off the songs my friend put on there. Oh well, Ill have to get them again.

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