1) When a character asks a question, don’t always have the other character answer it. – Many writers treat dialogue like a logical exchange of information. If someone asks something [beep beep boop – I am a robot] the other character must answer. The second character will, in turn, ask a question, and the original character then answers it. That’s not true to life. Conversation is messy. Sometimes people leave questions hanging, assume they’re rhetorical, or even ignore them completely, and that’s okay.
2) If a character must reveal backstory, have them do so reluctantly. – There’s nothing more artificial than a character who willingly opens up about their past.
3) If it feels like the characters are speaking to the audience, rewrite the dialogue until it feels like the characters are speaking to each other. – This happens a lot when exposition is involved. The writer includes information that characters would NEVER say to another person, but they rationalize it by saying it’s not for the other person. It’s for the audience. This is where dialogue starts sounding bad. It’s got to feel like a conversation that would happen in real life for it to work.
4) The power of an unwanted third character. – You’d be surprised at how much more fun dialogue becomes when you inject an unwanted third character. An argument between a couple in their car can feel cliche. Put that same couple in a diner booth with a chirpy waitress who won’t leave them alone and the scene comes alive.
5) Occasionally insert exchanges where characters say the opposite of what they should. – I was watching the Amazon show, Forever (spoiler ahead). Maya Rudolph’s friend is trying to get her to go to church to grieve. Maya doesn’t want to go. “Oh, you think you’re too good for church?” Maya thinks for a second. “Yes.” Or here’s an exchange I read in a recent script between two siblings – Brother: “Dad died.” A long silence. Sister: “About time.”
6) Make it so your characters have to come to a conclusion about something. – Bad dialogue is often conversation without a point. An easy way to hack this is to make it so your characters are trying to come to a conclusion about something. And, of course, they don’t agree on how to get there.
7) If it’s bad dialogue, it’s probably a dull situation. – The best dialogue is derived from interesting situations. If you place your characters on a porch with nothing to do but talk, chances are the dialogue will be random and aimless. But if you place the same characters on a floor in the middle of a bank robbery they’re trying to escape from, their conversation is captivating. These are extreme examples but the point is: the more captivating the situation, the more captivating the dialogue.
8) Give one of the characters a secret that affects the other character. – A scene where two people are talking about work is boring. A scene where two people are talking about work and Character A knows that Character B is going to be fired later today is cringe-inducing (in a good way).
9) The correct answer to a question isn’t always the best dialogue option. – In Hell or High Water, our bank-stealing brothers are squaring away their mortgage payment with the trust executor, a man who knows they stole the money. The troublesome brother is skeptical of the executor, and keeps asking him tough questions. His final question is: “How much are you making off this transaction?” Now think about that for a second. The executor knows the exact amount he’s making. But is that the best answer for this dialogue exchange? Is “1200 dollars” a good line of dialogue? No, it isn’t. You want to know what he says instead? “Not nearly as much as I’m risking.” Now that’s a good line of dialogue.
10) Play the opposite emotion of the setting. – Two characters joking around and laughing at a funeral is more interesting than the typical depressing conversation you get. Likewise, two characters having a really depressing conversation at a wedding or a baby shower can turn a cliche scene into an unexpected treat.
