Truth or Dare for Your Writing by Wyatt G. Bessing

Dare MeWelcome back to our monthly columnist, Wyatt Bessing. A writing coach and teacher, author, as he shares with us “Truth or Dare for Your Writing.” Enjoy!


Do you have a secret crush? On whom?
What’s the naughtiest thing you’ve ever done?
Put an ice cube in a sensitive place.
Run across the street… naked!

Did you ever play Truth or Dare when you were young? It was probably thrilling, testing boundaries and building trust among your friends. As you said and did wilder and wilder things, your relationships grew stronger and the world opened up to new possibilities. Yet we grow out of Truth or Dare eventually, finding the dares childish, the truths too painful to admit. We learn to guard ourselves too deeply, developing layers of protection. It’s part of maturity, to cast off the play and games and experimentation of childhood.

But as writers we must continually rediscover that sense of wonder and invention, that fresh way of seeing the world and welcoming its risks, testing its boundaries. By facing risks and asking the difficult questions, you’ll develop a relationship with your reader and open up new possibilities and avenues to explore within your story.

Be daring and tell the truth to keep your readers excited.

In Natalie Goldberg’s famous book Writing Down the Bones, she suggests that writers see the start of their daily writing practice as jumping into a lake fully clothed. You’ll get used to the water as you swim, and then, as you make your way to the other side, you gradually remove your clothing so that once you’ve made it to the other side you’ll be gloriously naked and gloriously alive. Just plunge in and start writing, and let the wildness and risk come to you as you swim away from that safe shore toward the place of no return. It feels good and free; and if it’s a bit uncomfortable and risky, you’re approaching something deep and important and your readers will be all the more excited to come along for the journey.

Here’s a game to play as you write your work-in-progress. Set a timer for ten minutes, writing in manageable bursts of energy. Don’t overthink it, just write, letting the words flow out and escape that internal editor telling you the difference between right and wrong.

  1. When the buzzer sounds, roll two dice, and consult this chart:
  2. Dare: Remove an article of clothing in an alluring way. This could be interesting if you’re writing in a public place!
  3. Truth: What was the most embarrassing thing that ever happened to you?
  4. Dare: Call or email a friend. Read or send them a part of your story.
  5. Truth: If you could kiss anyone right now, who would it be?
  6. Dare: Put an ice cube on a sensitive place on your body.
  7. Truth: The worst mistake you made was….
  8. Dare: Run outside and dance around right now.
  9. Truth: Do you regret anything you did in life? What was it?
  10. Dare: Write a letter to someone and tell them how you really feel.
  11. Truth: What was the most sensual moment of your life?
  12. Dare: Take the rest of the day off from writing. Go on an adventure.

Here’s the twist: You can perform the dare or answer the truth yourself, or you can make a character in your writing do it. Use these questions or dares to challenge yourself and to learn more about the characters you’re writing.

Keep resetting the timer after each burst of writing and Truth or Dare roll, going into deeper and deeper waters as you risk and write dangerously!




Wyatt Bessing is a writer, writing coach, and learning specialist. His stories and essays have appeared in, Outsider Ink, national educational assessment materials, and in the anthology Dance, Human Rights, and Social Justice. Through his workshops, website, and blog at, he guides new and experienced writers in crafting more effective, expressive, and striking work. During the day, he works at Star Academy in San Rafael, teaching reading and comprehension skills to students with learning differences in elementary through high school. He lives in Santa Rosa, CA with his wonderful fiancee and co-creator, Sarah Laugtug.

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