Just used Helvum from Flathub to watch a show on my laptop through my wife’s and my headphones simultaneously, and it worked flawlessly! Someone should make a GNOME extension to allow choosing multiple outputs, or something.
As nice as it was to be able to do what I wanted, it was definitely intimidating at a glance. But it was as simple as connecting both headphones over Bluetooth, then dragging the app to the headphones in Helvum.
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