iPod Need to add my iPod Shuffle to my iTunes library...

[Wheeltard]

this is absolute bull*****! My first generation iPod shuffle is not showing up in my iTunes library or as an option to sync. How can I get my iTunes library to recognize so I can fill it with tunes for my ski trip? Sorry to rant, but I have no idea why all of sudden it's not recognized by my library. This sucks. Any help would be greatly appreciated.
Wheels

 

[Wheeltard]

Anybody got any ideas? If there is an even less elegant way to load the shuffle, I'd be open to that too. This is just frustrating, and I'm leaving Tuesday. Any help would be greatly appreciated.
Wheels