HT204387 Can my iPhone pair with 2 different bluetooth headphones at once?

I want to know if I can playback music from one phone to two different bluetooth headphones at once so myself and a friend can listen to the same songs.

Don't remember if anyone has reported on this, but just give it a try. Here's an Apple support article on using bluetooth.
http://support.apple.com/kb/ht1664

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