What a great forum! I've been searching for an answer to this question, and though I have not found it, I have learned a bunch of other stuff!
I have a 2GB micro SD card on my 8800 loaded with music. How can I hear the music through my stereo/ipod headphones? It plays thru the handsfree speaker and the handset speaker, but not the headphones. I had to buy an adaptor to downsize the headphone from 3.5MM to 2.5MM.
go to Seidioonline.com and buy the adapter from there. The one you get at RadioShack or Best Buy doesnt work properly in the BlackBerry. The location of the connections is different than most other phones.
I found an LG headset at Best Buy for less than $20. Sorry, I don't remember the model. The sound is good, and the nice thing is it has an inline microphone, so if you get a call you can just answer it. It also has a volume control.