I've never tried to pair to a headset so I don't know if it would work but, I have tried to pair with my daughters iPod and wifes iPhone 3GS and it wo t happen. Tried ibluenova but no luck with that either. I've read about a cydia app to replace ibluenova called Celeste but it's not out yet. This is my main complaint about the iPhone. Seriously, it's the best and smoothest smartphone by far in my opinion. Apple needs to get this right. Anybody that has any Bluetooth info relative to pairing with another phone of any kind, I would appreciate the help.