20 Daring Writing Prompts

For this collection of writing prompts, the theme will be all about risky and emotional pieces of writing. They’ll be ideal for anyone wanting to write a more revealing and challenging article, story or blog post.

  1. Write from the POV of someone who has made you feel angry/upset.
  2. Discuss something that you really struggle with e.g. failure, body image, family.
  3. Write about your deepest fear.
  4. Write a letter to someone who used to or does put you down constantly.
  5. Make a list of your biggest regrets.
  6. Confess something that has weighed on your mind for years.
  7. Write about a time you got away with something really bad.
  8. Talk about how much you loved your first partner.
  9. Make a list of things you want to do but are too scared to.
  10. How do you deal with anger?
  11. Give advice on handling something challenging using personal anecdotes
  12. If you could change one thing from your past, what would it be?
  13. What do you miss most or least about your childhood?
  14. Have you ever been told something you didn’t want to hear?
  15. When was the last time you cried and why?
  16. What does the word “lost” make you think about?
  17. If you could change one thing about someone else, what would it be?
  18. Write about a toxic friend that had a huge effect on you.
  19. Write about a dream that you know you can’t achieve.
  20. Write a letter confessing your feelings to someone special.