How can two headset hear each other on one Xbox?

well to play online if one of the two accounts that you are using has xbox live gold, then both accounts will be able to play online at the same time. About the headset thing, i don't think you are able to do that just becase the console does not support
the entrance of two chanels of audio,

Yes, two people could play online at the same time, both with headsets, and join a party and talk to others, but the two may not be able to hear each other through headsets (because they're on the same console). So both users should be able to hear everyone
else, and everyone else hears both of them, but the two might not be able to hear each other through headsets and would need to rely on hearing each other without microphone/headset.

I hope this helps.

No matter what headset you use,official Microsoft or otherwise,you will not be able to hear someone on the same Xbox as you are through the chat.The Xbox stops two players in the same room from hearing each other through the headset
because of voice lag,echo and other things I think.I do believe Microsoft figured if two people were on the same Xbox,they would be in the same room and be able to talk to each other that way.Gaming headsets weren't really a thing when the Xbox first came
out.

It's a shame it doesn't work,but that's just how it is unfortunately.

If each of you is signed into an account on the console (both should sign in using a controller each), meaning you need two accounts, you should be able to make this work by both being in the party chat.

I have not verified this myself, but I have seen it reported that while you will both be able to hear all the others and they all hear you, you will not be able to hear each other through the headsets as you are on the same console and that would cause some
lag (where you hear each other 'in real life' and then a little after through headsets).

Let us know, but if you still want to call Support the number is 1-800-4MY-XBOX (1-800-469-9269).

However, try this first and see how that goes.

I and my son ran into the same thing today. I bought us both Logitech headsets for Christmas. We are able to play split screen, and we can talk to other members of our party. But we can't hear each other talk. The headsets block out most outside noise,
so even though he and I are sitting right next to each other, we can't coordinate with each other in-game.

Microsoft if you're listening, please add an option that allows two people with headsets, playing on the same console, to chat with each other *through* the headsets.