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Managing bifurcating conversations
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Dialogue should always be motivated by characters' wants and needs. Characters don't know readers exist, so they should never be talking to the reader. Explaining things to readers in dialogue only works when (1) at least one of the characters involved in the dialogue doesn't already know what's being explained and (2) the character doing the explaining is doing so because it's necessary to what they want/need. I mention this because too many novice writers (myself included, some years ago) write dialogue that is really an information dump for the sake of the reader instead of real interaction between characters.
As far as branching, that happens all the time in conversation, but dialogue is not raw conversation. It's cleaned up conversation, focused on the characters' wants and needs and removing repetitions, unnecessary digressions, ums and ahs, and anything else that doesn't help to either advance the story or reveal character. Branches are okay in dialogue so long as they serve a valid purpose in the story. If not, then they should be pruned.
If you're having trouble with convoluted dialogue, ask yourself what the dialogue needs to accomplish and focus on that. "What the dialogue needs to accomplish" has to do with advancing the story or revealing character (or both), but generally not giving the reader background, because characters don't know readers exist. You can get away with a little of that so long as one of the characters involved doesn't already know what's being revealed, and so long as the character revealing it has a reason to do so. But usually, background is better doled out in small dollops through narrative.
I hope that helps.

Thanks, Dale. This is good general advice, but this conversation is one of those situations where the main character is being thrown into a new and dangerous world. The amount of stuff he doesn't know is vast, shouldn't all be presented as exposition, and would require its own book to do a full "show don't tell." Thus it gets into the Detective Interviewing a Suspect area (although the other participants aren't suspects, and the main character isn't a detective).
I'm currently spreading the conversation across multiple scenes, with scenery and action designed to invoke the specific conversations. If a key clue to what's going on doesn't come up naturally in one conversation, I look for another where it can fit in. The inverse is that, for any one conversation, the points I've been following are the ones that are less likely to come up later, instead of the ones that I, personally, find most urgent to relate.
We'll see how it works out.

Okay. So it sounds like you're already trying to break it into several smaller conversations. I guess the key point is that if the main character is doing the asking because he realizes he needs to know something, that's fine. Or if another character is filling him in because they think he needs to know it (whether he realizes it or not), that's also fine. But the main character might not know he needs to know some things, and nobody else might think to tell him, in which cases those things would have to come out when his ignorance of them trips him up.
I'm just making vague suggestions, of course, since I don't know the actual situation and can only (vaguely) guess...
How do you manage such branching conversations?