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How to write dialogue well?

I really struggle with writing dialogue, mainly because I have trouble understanding people IRL.

How do you guys do it?

For me, I tend to imagine two people conversing with one another and just let my muse flow with some tangential notes to address certain plot points as needed.

It is a bit tricky, but I find that as a result my dialogue comes out strongly.

It also helps if you can figure out a 'voice' for a character. If you get good enough, you can write lines of dialogue without saying who is speaking and potent context clues alone will let the leader keep track of who is who.

My biggest advice would be to avoid letting dialogue just become a plot device (only important conversations, plot hooks, etcetera). Basically, don't be afraid to just have random ass conversations that are fun in the moment and have no greater significance.
 
It's a tricky thing I think. First off, read aloud. Try to roleplay the conversation. Keeping in mind how a character speak. Also, less is more usually. Try to not have long sentences for dialogue.
 
Thinking about Tarantino's dialogues, the thing I like most about those is that they make it both amusing and mundane at the same time. Like talking about what different burgers are called in France, or how one of Madonna's songs is all about big dicks. Dick dick dick dick dick dick dick dick dick. You take a mundane topic but have the characters talk about it in such a funny way that it makes you eager to hear what wild thing is going to come out of their mouths next.

That plus a lot of wit. "Did you see a sign outside my house that says dead nigger storage? Oh, you didn't. You know why? Cause there isn't one, cause storing dead niggers isn't my fucking business!"

Or there's also the Deadwood route where a bunch of crusty guys insert creative cuss words into everything they say. "I may have fucked my life up flatter than hammered shit, but I stand before you today beholden to no human cocksucker. And workin' a payin' fuckin' gold claim"

Also it can help to have characters interrupting and talking over each other sometimes, to make it feel more organic. I recall Curb Your Enthusiasm liked to keep scenes unscripted to allow this natural sort of dialogue to come out as the actors improvised. But it's hard to translate that to text, so I would use it sparingly.

A good place to start might also be to have one character tell a funny story, and splice in natural reactions from the other characters as you go along, like laughing, cheering, groaning, talking back, adding little quips like, "Hey Sarge, you'll get lip cancer smokin' those" (Bill Paxton in Aliens). Just random stuff that the reader doesn't expect that will keep him interested in finding out how the rest of the scene goes.
 
What's your goal for the dialogue? Do you want to be able to deliver exposition without sounding like robots? Do you have an existing dialogue but you want to make it more interesting or funny? Are you struggling with subtext?
My general advice:
- know who your characters are and even more importantly what they want. In real life, lots of people are weirdos. But two weirdos who want something from each other or want conflicting things can have an interesting dialogue.
- It also helps if you have something you want to say. If your story is about something, then choose characters who are drawn to talk about that thing.
- What's your goal for the dialogue? If you want if you just want to get it over so you can get back to the fun part, then find a way to say it in the least words possible. Always foll focus on the fun part of your story. On the other hand, if your goal is for a fun dialogue, have them say things that are fun to you.
- people don't always say what they want, if they're afraid or embarrassed about what they want. Let's say you have three guys and they all want to date this girl. One guy might try to make friends with the girl. Another guy might try to say a lot of things to impress her. And a third guy might talk about the flowers then blurt out that he thinks she's pretty.
 

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