If you go to My Media thing, then to RingTones and then (mine are on Device Memory, i don't have an SD card) and then you go to ones you put on there, i have that option...you hit the Blackberry option button, next to the pearl trackball and scroll down
If you're room mate has a Chocolate then I'm assuming they have Verizon. If so Verizon's blue tooth is crippled and the only thing they can connect to is a head set. So you wouldn't be able to send anything through blue tooth w/ anyone that has Verizon. I just barely switched from Verizon.