User blog comment:SweetCrazyYandereGirl/I'm stupid.../@comment-5235303-20121106214441

Do you have it set to "manually manage music" or something like that when you connect your iPod? If it still doesn't work you should check if you can listen to you mp3's on your computer. They might be corrupted (happened to me once -_-).

If the "manually manage music" button-thingy isn't checked off, then you first need to import your music to the iTunes library before you can add it to your iPod.

...Hopefully that made sense