How to Get Your Characters Talking (especially if you’re blocked)

Cy Tidd
The Startup
Published in
2 min readDec 31, 2019

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Photo by Peter Lewicki on Unsplash

Every fiction writer has looked at the last thing they’ve written in a character dialogue and thought, Oh, great, I just killed this conversation. I have no idea where to go from here. Crap.

I’d sit there and glare at the page. Sometimes I’d end the writing session and leave frustrated. I’d come back frustrated, and find myself in the same spot. Days might pass before I climbed out of the hole I dug for myself.

Turns out, there’s a simple technique to get going again.

The Trick

If you’ve never heard of it, I encourage you to read a wonderful book called Wait, What? And Life’s Other Essential Questions by James E. Ryan. In it are five basic questions that I use to get more meaning out of my life. I also use them move conversations along in my stories.

The trick is to have your character ask one of these questions. You can’t help but answer it.

Your writing block turns into a river of words.

Wait, what?

My favorite question, in both fiction and in real life, is “Wait, what?” There’s so many things you can do with a “Wait, what?” Perhaps restate the original premise. Maybe come up with an interesting metaphor to explain a concept. If the characters are antagonistic towards one another, it spawns more conversation and conflict.

I love these two words.

That’s it. Simple. The best tricks are.

Other dialogue tips since you’re here:

  • People talk by exhaling air. Make sure the things they say can be done on a single breath. Your dialogue will flow better.
  • Exclamation points are rare in the wild. Treat them like a precious resource in your writing. I’m working on a manuscript with 100k+ words. There are 7 exclamation points in it. You can have lively characters without overdoing it with “!” everywhere.
  • If you want to write better conversations, then you need to be able to have better conversations. Much like if you want to write more convincing stories about, say, jousting. The person who jousts can write better jousting scenes than the person who’s just researched it on the Internet (note: I cannot joust). If you can carry on a conversation for more than two minutes, then you can likely write a good one, too.
  • At some point, you’ll want to dump in some exposition. Sometimes you might remind the reader about something that happened already. But you don’t want to repeat yourself. Get a character to do it for you. Sprinkle in some “Wait, what?” here and there and it’s like magic. You can break all sorts of rules.

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Cy Tidd
The Startup

I write books and software. Opinions held loosely.