How do I put any media of any kind on my iPad?

There is no dvd drive or usb port. I finally resolved that if I want to use the iPad for its only discernable purpose—watching movies on an airplane—I am going to have to buy them from iTunes.* Now it is telling me that the date and time are wrong (they aren’t) and that it can’t establish a secure connection, so it refuses to download anything. I have resynced it with iTunes to no avail.

How do I solve this? And apparently 95% of people are satisfied with their iPads. Am I an alien? I hate this f-ing thing.

*if I am wrong and there is any other way to do this please tell me