Can't download songs onto iPod Shuffle! PLEASE HELP!!!

On iTunes, I have a lot of songs checked off to go onto my iPod Shuffle. When I click on Autofill, none of the checked songs appear, only the unchecked ones. Can someone please help me??
  Windows XP  

Is nobody answering because it's too hard of a question?
(sorry, I'm a little impatient right now, I just got my iPod Shuffle for Christmas, and this shouldn't be happening! It's driving me crazy!)

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