Question about your headset (not OBS), does all sound on your system come out of your headset, or do you have it set up so that skype/teamspeak/etc come out of your headset, and then your game/desktop comes out of your speakers?
OBS appears to be working fine. I'm sort of curious as to what OBS does pick up in this case. It should pick up everything if that's how you have your headphones output set up. You don't have a xonar sound card do you? If you do, make sure to go into its settings and disable GX mode.
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