Going Deep into Conversation
7 Exercises to Level Up Dialogue
⋙ Master the Fundamentals, Keep the Streak Alive ⋘
Bookmark these daily “streak savers” from Writing Streak.
Dialogue can be delightful—unless, of course, you’re an author trying to write delightful dialogue. For the reader, good dialogue feels like a fun puzzle or a fascinating game of chess. As social animals we love to pick apart the layers of meaning in a good conversation.
Writing this kind of dialogue can be cognitively demanding. Hard work. Speech has so many functions. I like to think of dialogue as a layer cake where you have author intent, externality, internality, and reader interpretation stacked on top of each other.
The bottom layer is author intent where you are using the characters a bit like puppets to drop exposition, communicate with each other, and move the story forward. Basic plain vanilla dialogue. The second layer of the cake is externality where we add conflict, manipulation, and maybe even some forms of external distortion. The third layer adds internality to the flavor profile. What sort of internal conflicts and internal distortions surface? Finally, the icing on the cake is reader interpretation. These are the delightful bits we add to the dialogue to just plain entertain the reader, like voice, humor, and wit.
Dialogue doesn’t have to use all of these layers. Sometimes your reader doesn’t want the whole slice of cake. Or maybe you’re still learning to bake that first layer. That’s fine. Work where you’re at, but add just enough challenge to level up your dialogue.
This Week’s Streak Savers 🪦
⋙ Monday, Feb 17: A Casual Conversation
Setup: A conversation that will transition the story to a new chapter.
Goal: Write dialogue that informs, communicates, and/or moves the story forward.
Constraints:
The first lines must weave in story exposition
Focus throughout on characters communicating information
The last lines lead to a clear next action
Modification: For a bit of fun, write some “maid and butler” dialogue using phrases like, “as you know”, while setting up the next chapter.
Reflection: Did the dialogue sometimes feel a bit too “on the nose” i.e. lacking subtext or nuance?
⋙ Tuesday, Feb 18: A Subtle Manipulation
Setup: A character needs something but doesn't want to ask directly.
Goal: Write dialogue where one character slightly manipulates the other without showing their hand.
Constraints:
The character can't state what they want
Don’t have the character lie
Their true goal must be clear to the reader
Modification: As a challenge, create a more direct conflict where both characters want something.
Reflection: Was it difficult to signal intent to the reader while creating a reasonable manipulation?
⋙ Wednesday, Feb 19: Dialogue with Distortion
Setup: Two characters are trying to resolve a conflict.
Goal: Write dialogue where miscommunication increases the tension.
Constraints:
Start with both characters trying to make things better
Include a misunderstanding, exaggeration, or misdirection
End with their relationship deeply wounded
Reflection: How did the conversation's tone shift when the distortion occurred?
⋙ Thursday, Feb 20: Dialogue with Inner Conflict
Setup: A character must respond to a request they're unsure about.
Goal: Write dialogue that hints at a character's inner struggle.
Constraints:
One character must ask for a clear yes/no decision
The other stalls, clearly conflicted internally
Write until someone exits the conversation
Reflection: What subtle ways did you show the character's uncertainty?
⋙ Friday, Feb 21: Dialogue with Delusion
Setup: Think of a character with a slightly eccentric belief or self image.
Goal: Write dialogue that shows how a character's inner world distorts their perception.
Constraints:
Start with normal conversation
Gradually reveal the character's warped perspective
End with the character doubling down
Reflection: How did you balance making the distortion clear to readers while keeping the situation believable?
⋙ Saturday, Feb 22: Dialogue with Reader Appeal
Setup: A charismatic character meets someone who's all business.
Goal: Write dialogue that makes readers grin using voice, humor, and/or wit.
Constraints:
Make your fun character's voice distinct
Keep the other character's responses stiff
End with the stiff character warming up
Modification: Make your character delightfully unlikable and challenge the other character to remain civil.
Reflection: What dialogue choices made your character most entertaining?
⋙ Sunday, Feb 23: The Many-Storied Dialogue
Setup: Choose a dialogue between two characters where one is telling a story.
Goal: Transform basic dialogue into something complex and delightful by adding layers one at a time.
Constraints:
Write a simple exchange that simply tells the story
Revise or rewrite to add external conflicts or goals for both characters
Add internal conflicts or distortions for at least one character
Edit or redraft to add elements of voice, wit, or cleverness
Modification: As an added challenge, try working each layer backward, from voice, to interanlity, to externality, and finally to the story progression.
Reflection: Which layer changed your dialogue the most? Was there a level where you felt most comfortable working?