How did you rip your music. you have to use Itunes.
down load itunes from apple.com
go to import music from folder and go to my music folder and bingo all your music will be in a language that your ipod will read.
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this is what you will do, when you sync it again stop the automatic sync the click on your player on the itunes window to see its details, you will see 3 or 4 checkboxes and check manually add music or songs and ucncheck if there is any, the box that says automatically sync music, then click sync, it will start syncing again the disconnect. add songs only to the folder where itunes have got the songs so that next time you sync the ipod the songs previously added wont be erased.
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When you connect the ipodnano to the computer, you can do one of two things: you can go to the ipod's main home page in itunes and go to the bottom where it will have four options listed. 1 of them should say manually manage files. Click on the check box next to it and it should ask you if you are sure and click yes. Then go into your music folder of your ipod and delete the songs you don't want on there. To add music, all you have to do is click and drag what you want onto the oped. The second way you could do it is to go into your library before connecting your nano to your computer and un-checking all of the boxes next to the music you do not want on your nano and then connect it to a computer and let it sync. The first way is easiest and less time consuming as you only have to do it once. Hope this helps!
try restoring the ipod, go here http://support.apple.com/kb/HT1339 for instructions. Once it has been restored to its original settings you can just sync your music to it again, and hopefully this will resolve you problem.
You can get the files from an online music service like iTunes, Napster, Rhapsody, Limewire, Bearshare, etc. Or you can use Windows Media Player 10 or 11 to "Rip" songs from a CD - I would reccommend ripping them in mp3 format.