I've had issues with my bluetooth headset connecting, too.
I've had some luck in trying to connect with the applet, and then restarting 
the headset.
If you run bluetooth-applet from a command line, does it tell you anything 
useful? I've noticed mine saying
"No supported protocols on device"

-- 
bluetooth headset detects and authenticates against bluetooth stack but fails 
to connect
https://bugs.launchpad.net/bugs/432842
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