: How to plan dialog and keep it on track? When I'm writing a plotline, it often works out that I know two characters will be meeting each other in a particular scene, and that they will converse.

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I've discovered from experience that whenever I try to shoehorn my dialogues into how I think they should go or how I want the scene to work out, they always end up very stilted and unnatural.

The method that I've found works for me is only having an end-state in mind. That is, Person A should now have this knowledge, Person B this knowledge, etc. And then maybe something like "Person A should feel like they're trapped".

Then I simply let the conversation flow between the two characters, no matter how it comes out (but always keeping the end-state at the back of my mind). Sometimes I'll achieve the exact outcome I wanted, other times it means I need to rethink either this scene (is this really the best way to convey this information?) or rework previous/future scenes (can this happen/be conveyed in another scene instead?) - but I find that doing this makes for much more natural dialogue.

As always, YMMV on this - it's very much a character-driven approach and relies on you being very familiar with how they think and act. It does also mean that I need to go back later and revise the dialogue, because natural speech =! effective writing.

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I have a somewhat unconventional style so I don't know how much use this will be to you. Most of my dialogue is intended to convey meaning in some form or another, or to illustrate something about one of my characters, so I consider carefully what my protagonist will say and what the responses will be beforehand. I have to do this to make certain that all of the information I want to convey is conveyed and no more than that. Most of my fiction is odd in that it's told from the perspective of a potentially unreliable narrator, who may not want to share information with the reader directly for his or her own reasons, and instead may wish to convey the information with clues in dialogue, and that's the reason for the careful consideration. I hope that helps you.

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A little riffing, a little planning.

I tend to sketch out a scene in notes and bullets beforehand, so I know more or less where it's going and what I want to accomplish. I'm "watching" the characters interact in my head as I'm jotting down notes, and sometimes entire exchanges come out of that.

Once I've roughed out the scene, then I can go back and tweak to make sure it does what I need it to do, and that the characters are true to how I've envisioned them. Sometimes I have to back up and say, "But Malcolm wouldn't pry like that. This whole section has to go" (massive deletion of text) "so how would he get Charles to open up?"

How the people actually get to where I'm aiming them is all ad libbing, but you should have a good idea of each character's voice so that it doesn't take you by surprise or wander off into the living room. You should know them, as people, and be able to predict how they're going to react.

If you don't know your characters well enough, you have to go back and spend some time with them — maybe doing those silly personal quizzes which get emailed around, answering it in the voice of each character. (I actually find those incredibly helpful.)

So your questions about when they would start and stop talking is up to you, or up to them, in a sense. Those questions aren't going to be answered necessarily by just clattering away at the keyboard like an infinite monkey and hoping that A Midsummer Night's Dream comes out. You have to figure out how your character is going to react to your other character, and write the scene accordingly.

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