I can't figure out how to do it, I have tried a few different programs but can't get them to work. My buddy uses handbrake for his MAC, but that doesn't help me much. I need something that will work for my PC version, can someone help me out here?

You need to convert DVD or video files to iPod mp4 format and then sync to your iPod with itunes.
Check this great guide http://forums.afterdawn.com/thread_view.cfm/253137