Running Two Bluetooth Headsets

[TInSOMD]

I bought a second BT headset so that my wife and I could watch movies together on long trips. Both headsets pair, and both play correctly when I make each headset the default, but I can't make both of them play at the same time.

Should this be possible, or is it a system limitation?

If it's not possible to connect both at once with BT, can I connect one with BT and run the other wired, and get audio from both at once?

Since only one headset has the wired option, just using a splitter on the wired output isn't an option.

 

[sharpuser]

Here's one thing I do - converts any headphone or audio receiver to Bluetooth. Simple.

Your Surface or smartphone or other source can transmit to headphones (Y-Adapter for multiple) or other stereo receivers or sound systems with Auxillary input capability.

Griffin iTrip Clip Bluetooth Headphone Adapter