My Droid X Bluetooth will receive files from other devices, but will not send files to the same devices. Bluetooth headset works great. When attempting to send files, it doesn't even try. It fails immediately.
What type of files are you tring to send because I have had no issues sending either way?
UPDATE: Just did some testing and it seems that size may be a factor in this situation, what device are you trying to transfer to? It seems spartphone to smartphone it will send but when I tried a coworkers regular Sanyo phone it would fail..
Download bluetooth file transfer from the market, works every time.