What is the target device are you sending it to? If the target device is an iPhone, there's no way without first jailbreaking the iPhone first before being able to share files.

I was trying to share some music with one of my workmates (or you can say work colleagues) which happens to have iPhone 4. The same sort of scenario happened where pairing was possible but I just couldn't share my music from my N900 to his (un-jailbroken) iPhone 4. He said stuff about how Apple doesn't allow this sort of functionality. Initially I did not believe him but later on when I checked the list of bluetooth devices that I have paired previously has viewable profiles that each of the paired bluetooth device has, every one of them except for iPhone 4. My old N95-1 has various bluetooth profiles, both my other N900 has bluetooth profiles, my bluetooth headset has bluetooth profiles and my other workmate whom has a cheap android device has bluetooth profiles. As of now I found out that this is actually the case (have a read here).

(edit) I have no problems whatsoever with sharing files between other bluetooth capable devices, all except for iPhones.