5punk

Me and Mrs. J would like to watch something on my PC together since her laptop is struggling with HD files but since I no longer have a stereo set we have to listen in through two different headsets. This seemed like a pretty straightforward thing but apparently it's not that easy to do on windows and I'm struggling to find the solution. And both headsets are USB connected.

Any advice?

This is the easy way, assuming you have non USB headsets.

I had luck in the past playing audio from optical, and analogue out on my soundblaster based soundcard (auzentech x-fi prelude) but it was a bit of a clusterfuck as far as settings go, was always accidental when it worked.

Otherwise, there's possibly the option of using front and rear ports, but I dunno how they'll play together.

Edit: Just noticed the USB thing, basically, I think you're fucked. These are probably cheap enough for you to afford, and will do the job but not a great deal more.