If you trying to play on headphones, you need the stereo adapter 3.5 to 2.5 sold at a verizon wireless store. Or you can order the Seidio brand here at the CB store.
Most other adapters are not BB compatible.
Posted from my CrackBerry at wapforums.crackberry.com
When I use a mono headset for the PHONE, the headset works fine. When I use the headset to play MUSIC, it does not work.
When playing music, there are two options - Activate Speakerphone and Activate Headset. When I select Activate Speakersphone, it plays through the speakerphone (as it should.) When I select Activate Headset, nothing comes out of the headset, and sound still comes out the speakerphone, very low volume.
I tried doing this with stereo earphones, using a 2.5mm to 3.5mm adapter - same thing happened.