This is a toughie! I used to be the same way, actually. And then one day, I suddenly started getting compliments on my dialogue. It was so surreal!
The big things here are research and practice.
Find books, movies, and TV shows that you think have realistic dialogue. Learn from them. Just sit and absorb the naturalness of it.
Then find some pieces of media that don’t have good dialogue. Make notes–what is it that makes them unnatural? What are phrases that no actual person would ever say?
The next step will help if you’re stuck on that. It’s eavesdropping! Go sit in different types of public places and just listen in on people. How do they talk? What mannerisms do they have? How does their language differ from “perfect” grammar? What words would you use to describe their way of speaking? Take as many notes as you can!
Try libraries, parks, restaurants, cafes, movie-theatre lobbies–anywhere you can find large groups of people. Do what you can to think outside the box on that.
Some other things you’ll want to start doing is just reading it out loud to yourself. What parts do you get stuck on? What sounds unnatural? Trust your instincts.
Once you’ve made your progress, get two (or more) people you know to read one of your new stories out loud, each person doing the dialogue for a different character.
Listen to them and answer the same questions you asked yourself–where do they get stuck, and what doesn’t sound natural?
Let them give you some pointers on how they think the characters would talk in those situations. They won’t be 100% accurate since they’re your characters, but they can tell you if it sounds like a conversation an actual set of people would have.
While they’re reading, resist the temptation to help them out. Your story may one day be read by people who don’t know you or anything about you. You have to let your baby fly on its own if you want to make sure that it is understandable to people other than yourself.
That’s the thing: other people will be reading your dialogue in the future.
They don’t have context of who you are or what you’re like. They can’t get inside your head and psychically know what you were trying to achieve.
This is where technique comes in as part of writing as a craft. It might sound good to you, but if it doesn’t work for other people at all, then you need to work on doing better.
If you’re learning to be a carpenter, then you need to be able to make a chair that lots of different people of different weights can sit on. Your chair can’t break apart the second someone sits down on it. It has to fulfill its purpose as a chair.
Just like the chair, your story has a purpose: to be understood on one or more levels. If your story is written well, then it will be understood on a direct level and on a level that’s more spiritual, more about the heart of the story than what it directly says.
As much as it sucks, the key is to practice, practice, practice. You aren’t going to get good at dialogue overnight. You have to put your mind to it, but if you can do that, then you’re golden. 🙂
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