Here’s the thing that’s so tricky about it: People talking in real life are boring. If you transcribed most human interactions, no matter how packed with information or sparkling wit, you’d wind up with a lot of repetition, "uhs," "ums," and "likes," and giant chunks of talky-talk that don’t take the conversation anyplace.
Some of that is because there’s a lot more going on than just talk when you’re face-to-face. Gestures. Expressions. Social nuance that flows from the speakers’ backgrounds with one another. But more than that, real-life conversation is interaction, two people engaged in communicative give and take. There’s no further purpose to their words.
But in fiction, we also need to tell the story with each sentence. If you’re not doing that, those passages don’t belong in your book. So when you write dialogue, the characters are doing more than just pass the time—at least they should be. They’re advancing the plot in some way, whether through description, backstory, character development or conveyance of some bit of crucial information.
And that’s what makes it tricky. Your characters can’t "sound natural" because they’re not talking naturally. So how do you address this?
Once you make sure that your characters’ chatter isn’t just filling space, the easiest way to make sure they sound somewhat normal and not "written" is to read their lines aloud, preferably to someone who is not you. And that will help you develop an ear—or eye—for what sounds good on the page.
But don’t become too conscious of what you’re doing. I know. I know. It’s kind of Zen. And by "Zen" I mean "occasionally frustrating as hell." Here’s the way Elmore Leonard puts it... and Leonard writes the best dialogue of any novelist on the planet:
"I just make it up. Don't you hear people talking in your head? You think of a certain character, and you hear them talking. And from the way he talks, his character has attitude. When you see a character coming that you've met before, you know what his angle is going to be, what his beef is or if he's funny. So that I'm always writing from their point of view, and I'm never writing from my own."
What he said. Write a lot, read it aloud and try to let each character talk to you. I guess when you look at it that way, it’s not so tricky after all.
[Recommended Reading:
-"On Writing," Stephen King.
-"Negotiating with the Dead," Margaret Atwood
-"This is the Year You Write Your Novel," Walter Mosley
-"From the Depths," Gerry Doyle]
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