I know it doesn't, in that I know you don't share all information with your friends by any means. But I think it would help him trust me in the sense that you'd be making choices about information for yourselves, instead of through me. You're both most worried about messin' up my relationship with the other, so what I'm trying to find is something that will take me out of it.

I wouldn't tell him anything from you since that would be your choice to make, just as it would be his choice to tell anything to you. The only things I'd tell him would be my things, which is what he actually wants from me. Neither of you would have to decide on trusting me based on whether you trust each other.