Can't transfer songs from itunes to ipod touch

For like the tenth time since I've had my ipod touch I can't transfer songs from my itunes to my ipod. Usually it is because I need to update both my itunes and ipod and what do I know there is another update I need to do this time too. So I do both of them but this time it doesn't fix the problem. They are both up to date, when I try to transfer the song it just gets stuch on preparing to update and that's it so at the moment I can't transfer any songs on to my ipod please help.