First, make sure the iPod software is fully updated and you have iTunes 8.1. Second, with the iPod connected, go to the Store menu, authorize the computer with the account the video was purchased on. Third, are you trying to sync the TV show over or just drag it over? Another thought, did you purchase the show in HD or SD? HD purchases cannot be transferred over, but iTunes downloads a SD copy as well and should know to sync the correct version over...