I found this on a blog for some one else who had the same problem
1. The last time it worked I was using Mac OS 10.4. This allowed for file transfer via Bluetooth in a slightly different manner than 10.5. For example, when the bb connects to the computer, it loads the OBEX service (drivers) to the device and effectively open the blackberry up for object exchange (file transfer). From what I can tell, this service is now a clandestine part of 10.5 whereas, in 10.4 it was overt. What does this mean?
2. This means that in 10.5 the services do exist and file transfer is still possible, but more steps are required to achieve the desired results.
3. First, make sure both devices (computer and blackberry) are in "discoverable" mode and have been paired.
4. Perform the following in 10.5: select a file from the computer via the Bluetooth File transfer assistant - select "send file via Bluetooth" - Now, set the blackberry to "Receive file via Bluetooth" - doing this it will enable the device to receive the file and, seemingly enable the obex file transfer service. Once it completes, send a file in the other direction (from the blackberry to the computer). It should work.
I think the disparity occurred when I upgraded from 10.4 to 10.5 because 10.4 did not require so many steps to perform to complete the file transfer. I think Apple must have changed something in 10.5 and made it more difficult, or was trying to hide the obex service (maybe they considered it a security issue or something). Who knows? I hope this helps.
