I just bought my sone a Nano for his birthday- we downloaded songs from iTunes but when he tries to listen to them, the Nano just skips right through his song list without playing them. I cannot find ANYWHERE how to correct this! Can anyone help?!
Try restoring your iPod, someone else just had the same problem and the restore fixed it. Sometimes data on the iPod gets corrupted, and it doesn't remember where to find the songs it has put on the iPod. If you arn't already, try using a USB port on the back of the computer instead of the front to help prevent this.