Tootsie

Writing prompts inspired by the movie Tootsie.

Before we get to today’s writing prompts, let’s start with some inspiration from novelist Amy Tan:

“Everybody's — everybody's novel is semi-autobiographical. I mean, you have questions, or the way you think of life, or the kind of people you think are interesting — or not interesting. People who have impacted your life and made you who you are, that's who you put in your story. So they're all autobiographical. People say it's autobiographical even if I have written about a ghost, you know? When I'm writing, what often happens is — are strange coincidences, and then I think, these are the clues. It's like a little thing I have to follow, and I keep following more coincidences. I'm on the right track. And then I find something that is shocking, that maybe my grandmother was a courtesan. You know, my mother had been in jail. All of these things come together, and they make sense. Fiction makes those things happen faster, because I let myself go, and I'm not as self-conscious. But all these things from the past, they somehow rise up when you let go and say it's fiction.”

How much autobiography do you put into your fiction? I’d love to hear your thoughts in the comments below.

Okay, now let’s get busy writing.

Today’s prompts were inspired by the movie TOOTSIE. It’s a perfect screenplay. The characters are complex and flawed and real. As you’re writing today, I want you to think about how you can draw out your characters’ flaws more.

EXERCISE #1: 

“You’ve got a terrific face.”

JOURNALING PROMPT: Give yourself a series of compliments. Keep giving yourself compliments until it begins to feel uncomfortable, and then push through that discomfort. Discover as many little things that you like about yourself as possible.

FICTION PROMPT: If you’re writing a narrative, who is the character in your story who you know the least? Give this character 30 compliments. What are 30 things you like about this person? Don’t overthink it. If you get to 30 and there’s still time, come up with more compliments.

EXERCISE #2: 

“Turn the tables on me.”

JOURNALING PROMPT: Who do you want to confront? Fill yourself with confidence and swagger and write down everything you want to say to this person.

FICTION PROMPT: If you’re writing a narrative, write a scene where your protagonist confronts someone from their past. LET THEM GO OFF. Even if it’s out of character for them, write them at their BOLDEST.

EXERCISE #3: 

“No one wants to work with you.”

JOURNALING PROMPT: Face a hard truth. What is one of your faults? Something you don’t want to admit to. Freewrite about how this thing has gotten in your way in the past and how you might change it.

FICTION PROMPT: If you’re writing a narrative, write a scene where a character gives your protagonist some tough love and says something they don’t want to hear.

BONUS ELEMENT: Try to include a kiss in the scene.

EXERCISE #4:

“I don’t trust a man who won’t meet my eye.”

JOURNALING PROMPT: What are your personal deal breakers? (In either romantic or platonic relationships.)

FICTION PROMPT: If you’re writing a narrative, write a romantic scene for your protagonist, but whoever they’re with does something that they cannot recover from.

BONUS ELEMENT: Include some sort of unusual, uncomfortable, or difficult act of weather.

EXERCISE #5:

“Nighttime Drama.”

JOURNALING PROMPT: What’s the soapiest thing that’s ever happened to you? (Soapy as in soap opera.) Write out that story.

FICTION PROMPT: If you’re writing a narrative, write a scene where someone makes a dramatic revelation. Something that takes your protagonist by surprise. Some additional ingredients to include: something eaten, something thrown, something caressed.

EXERCISE #6: 

“Why should you move out?”

JOURNALING PROMPT: There is something big you’re afraid to do. What is it? Talk yourself into doing it.

FICTION PROMPT: If you’re writing a narrative, write a scene where another character encourages your protagonist to make a change in their life.

BONUS ELEMENT: Think about including a unusual moment of physicality.

EXERCISE #7: 

“Put some make-up on it.”

JOURNALING PROMPT: What do you wish you could hide or change about yourself?

FICTION PROMPT: If you’re writing a narrative, write a monologue where your protagonist talks about one of their imperfections.

EXERCISE #8: 

“This is some other girl’s candy.”

JOURNALING PROMPT: Think of a time when you took something that wasn’t yours, either accidentally or intentionally. Walk yourself through the ramifications of that.

FICTION PROMPT: If you’re writing a narrative, write a scene where your protagonist steals something from someone.

BONUS ELEMENT: Include a lie.