Thank you so much for your help! (My boyfriend does have different taste in music, haha)

Well I called the support people and they did get me to download the new version of itunes and the ipod updater. So I did that and then they asked me what kind of files the songs where and they were all downloaded as MPG-1 and ipod does not recognize those they had to be MP3 so I just needed to convert my songs. So I'm doing that now.