iPod PC / MAC query

I'm buying my boyfriend an ipod for Christmas and I am wondering if there's any way of putting the music I already have on my iTunes onto the iPod for him? The reason I ask is because all my music is on a Mac and when I tryed connecting my iPod to my home PC it said I need to format the iPod to use it on the PC (and I presume I'd lose all the music). My boyfriend will be using a Windows based PC/Laptop so has anyone any ideas?

it's possible to do it alright although you'll need to be a little bit savy if this guide that i came accross is anything to go by

[broken link removed]


best of luck with it.

Will the Apple DRM not prevent you syncing iTunes on one computer with more than one iPod? In any case isn't the original poster basically asking how to illegally share copyright material?