Dan asked David Wong:

Having read JDatE, I have to ask: does the dialog come naturally, or do you have to think about "how would this guy talk to that guy?" I find when I write, I can produce some "natural" dialog, but I always seem to question my decisions, then rework or rephrase, and I rarely get a natural, "organic" flow. A lot of my conversations feel contrived. Just looking for some pointers from a success. Please and thank you.

David Wong There are a few tricks I used that will become obvious once you know about them, but one thing that separates real talking from fictional dialogue is that the former is messy - people interrupt, they don't answer the question, they evade, they don't hear what was asked or choose to ignore it, they rarely clearly state their intentions, motivations or desires. Everything is cloaked in jokes or sarcasm or deflections.

Those imperfections are what (I think) makes it feel more natural to a reader versus people delivering plot points to one another. BUT there is a high degree of difficulty here, because the dialogue still has to serve the same purpose - you come into a scene knowing, "Here is where Bob finds out his boss suspects he's behind the missing documents" and you know that you have to get there before the scene is over. But you have to write it knowing that in a natural-sounding exchange, it's not going to be as simple as one guy making an accusation and the other guy trying to refute it, humans rarely approach things that directly and there are a lot of tangents etc along the way.

Doing it like this isn't easy and, in fact, lots of blockbuster movies and bestselling novels don't even bother. So I may not know what I'm talking about.

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