Q: What's the secret to humor writing?

A: In most character-driven humor you have to thwart people's expectations, and that provides a surprise. 

Q: Are surprises enough for humor?

A: No, you also have to have a particular tone. That signals the reader: this is funny.

There are surprises in Harry Potter that are funny and some that are not funny. When a character dies, that's a surprise, but it's not funny.

But there's a scene where Dobby's beating his head with a lamp in Harry's bedroom, and it’s pretty violent, but that IS funny. If you go back and read that scene, Rowling never pauses to inquire about Dobby's injuries. The story just moves on. That's the signal. The whole tone of the scene is "Don't worry about it."

That's essential in all humor, to get the tone right. You don't want your reader to start worrying about something that's happened. You don't want to create anything that's too near drama when it's supposed to be humor.

Q: What's your best advice for writing humor?

A: The number one thing is to recognize that, in your first draft, there is no way that you have jokes that are funny enough. They're all placeholders for you to go back and fix.

That’s because your brain always reaches for something it knows. (What you've written is probably somebody else's joke.) Or you'll read it and think: yeah, that matches up with what's supposed to be funny, and it will in the reader's mind too, except nobody will be laughing out loud.

And that’s okay. Write placeholder jokes that seem funny when you write them. But then you have to go back and make them better.

Q: How do I make jokes better?

A: Usually you will make a joke better by changing the wording and amping up how specific the details are.

For example: I’m writing a book about a cheapskate dad who takes his family on a knock-off Disney-like cruise that isn't legit at all. There's a mystery and the kid-hero, Charlie, gets very involved with the captain. The captain of the cruise ship is discussing what might happen to him if he ends up losing his boat.

In the first draft the captain said, “I’ll end up as a Starbuck's barista at the Miami airport!"

It was OK. The only reason it wasn’t completely awful was because I put “the Miami Airport" in there. Being specific is what makes it funny because, why the Miami airport as opposed to any other place? But it still was just ‘blah’, so over the weekend I started working on it. I don't think it's totally done yet, but I think it's way better than it was.

Now it says, “I’ll end up as a Starbuck's barista at the Miami airport, whipping up grande half-caf, half-sweet, coconut-milk, cinnamon dolce lattes for an idiot in a beanie who claims his name is Northeast Rainbow." Now I've taken it way bigger, way more specific. So that's how you make it bigger and funnier.

Then I added a second paragraph with our hero, Charlie's thoughts on what he's just heard. (And thoughts always provide a lot of room for humor. You can add some really outrageous things in thoughts that feel real because the person didn't say them ,they're just thinking them. That gives you a good insight into their skewed world view.)

Charlie thinks about what the captain has said and he thinks, “He would have thought that was extreme, except there was a high school kid on his block who wore a beanie, carried around a Starbucks cup wherever he went and was named Lobo Lupe Wolf. Lobo was Spanish for wolf, and Lupe was French for wolf, so his actual name was Wolf, Wolf, Wolf."

So that's how you take one little line and you blow it up by getting very specific