Problem with Syncing my iPod Nano

I got an iPod Nano a little over 2 months ago, and everything was going well until one day it wouldn't sync. I hit sync and it says my ipod is update but it isn't. I have plenty of room, and I've been doing things the same way for almost 400 songs and it just stop updating my iPod. What should I do? Please help me, I want to add my new songs!!! They are in my library but never show up on my iPod! Please assist me in solving this! Thanks!!!
  Windows XP  

Did everyone try the basic "5Rs" first? Mainly did you first try to reset the iPod and then if that didn't work, did you try to restore it?
Patrick

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