So, I will be going on a well-earned vacation soon with my wife. Flight is six hours long, so we’re looking at a way to get dual Bluetooths working on her laptop so we can watch a movie or two together on the flight.
I know this is possible since this very thing is solved by Pipewire in Linux, but Windows is a no-go. Anyone has better experience in this field? Is there an extra driver or something I can install?
It’s not even possible to play back the same audio through two different audio jaks without explicit driver support on Windows.
Audio bluetooth is a complete disaster with one headphone, two it’s basically impossible.
That explains why I couldn’t do it then.
Come on Windows, it’s 2021, bluetooth has been around for ages, you can connect two bluetooth headphones - do you actually mean to say you will cede decent Audio routing to Linux? Another nail in the coffin then…
They’ve been doing it for ages, it’s nothing new.
Beside giving a pointless answer to your question I’ve been thinking how you could get around this stupid limitation and got an idea: you could split the audio from a jack and plug in two bluetooth transmitter to pair to your headphones.
But this is where things get tricky: bluetooth is very sensitive to interference when transmitting audio so having two transmitters side by side might lead to jumpy audio or disconnections. I guess you could give it a try and if it doesen’t work return the transmitters.
BT is not a hard requirement, I’ll just do it like the nineties and use a $5 3.5" splitter as a last resort. It’s just, well… So stupid I even have to do that. And they call Linux the second rate OS… 
Yes, it’s beyond stupid. But it’s more important to change the goddamn start menu instead of improving things.
Have a good time on vacation!
Jackrouter and Virtual audio cable should be able to do it.
Ok, I did some more digging on this.
Windows does not, in any way, shape or form, allow two Bluetooth Audio headsets to be connected at the same time. This seems to be hardcoded into the system itself. Whenever I enable one of them the other is disabled. I think this is in order to be user friendly in case you want to put in a backup pair since battery is lost or something.
… But I found a way to easily share 1 BT + 1 3.5" headphone, so… YAY 