Ok, my girlfriend has an ipod touch, 1st gen, and she downloaded some episodes of a show she likes, and wants to watch them on her ipod touch. It gives her some sort of error, and says it cant play videos or something on it. She doesnt have the latest OS for her Ipod touch since 1st gen has to pay to get it, where 2nd and 3rd gen get it free. My question is, would upgrade the OS solve the problem or is it something else? Also, would Jailbreaking the phone (since that is legal now) get her to watch videos on her ipod, but without having to pay? Help a BF help his GF out here!