PURCHASED MOVIES WONT SYNC WITH NANO

ok first off earlier today i received a gift card in which i used to purchase 2 movies off of itunes.but 4 some reason i get the same message over and over again saying im sorry these files cannot be placed on ur ipod.at first i thought it was a new update or my ipod*which is new* but i had some spare vids on my comp in which i used to test and it turned out that every 1i used, worked. and ive been trying to contact apple rep's through some numbers i found and the lady i got basically blew me off and after that no one else picked up.........so ummmm yeah basically what im saying is HELP

What is meant by "cant seem to get any of my songs from my nano on to my i tunes account"?  This makes no logical sense.
All of your content should be in iTunes on the computer.
Connect the device.
Select the content desired to sync.
Sync.

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