Ipod Nano Help, Please Options

[Tramatize]

Well every time i try and put a show on my Ipod it usually says "The ipod Frank's Ipod cannot be synced. The required disk cannot be found."
So it doesn't work, and i have no clue what there saying with that whole "disk" mumbo jumbo, so i try once more and it does the same thing.
Well then i disconnect then reconnect and it usually works after that, but it doesn't all the time so i really dont know.
What happens when i get it to work is that it says "No disk found. Please enter disk into drive :F", and it has the option to say "Ok","Cancel" and "Continue", i hit continue and it works.
Can you help me find the problem?
It will be greatly appreciated!

[Sorry i posted this in the lounge if this isn't were it goes, i couldn't think of were it should be. Forgive me.]