My guess is this has something to do with parties. Make sure he is not in a party, even one by himself, and try again. The game prioritizes party chat.
Can he hear you? If he can then I'm not sure what is wrong
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this is on ps3 so we dont have a party chat... and no he cant hear me but he can see that my mic is on. and like i said he can hear the 3rd person and communicate through him to tell me stuff.
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Maybe he is muted? I'm not sure as I just joined the Sony team with the ps4