I love coming up with fiction writing prompts or exercises, and I think this list is particularly good for character development. You learn a lot about someone from how they behave in their most embarrassing moments, and this is a great way to create a sympathetic character.

I’m writing these as “you” statements because it’s less clunky that way. And you can use them as prompts for writing about yourself, whether you’re blogging, writing an essay, or writing a memoir. That takes some bravery, but people love to hear other people’s embarrassing stories. It helps them realize they’re not the only ones who get in those situations!


Cringe: 50 Creative Writing Prompts to Help You Embarrass Your Characters #fiction #idea starters #writing exercises #sympathetic characters


1. Your bra comes undone or the bra strap breaks.

2. You accidentally send an email or a text criticizing or mocking a person… to that person.

3. You break a chair or a fence you sit on.

4. You’ve gone to the wrong classroom, business meeting, or funeral.

5. You say something very personal to your best friend or partner and then realize someone else is in earshot.



6. You break a glass or spill a drink.

7. You unexpectedly have your period and bleed through your clothes.

8. You congratulate a woman on her pregnancy. She’s not pregnant.

9. You accidentally hug a stranger thinking it’s your parent or significant other.

10. You were only pretending to know about something, and then somebody asks you detailed questions about it.

11. You take a spectacular fall on stage.

12. You say the wrong thing during your wedding vows.

13. You walk into a pole or a wall.

14. You realize you’ve been calling someone the wrong name for weeks.

15. You show up for dinner on the wrong night.

16. Someone reads your private letter or diary entry out loud in a group.

17. You realize your shirt is on backwards or inside out (or both).

18. You’re underdressed, overdressed, or wearing something completely inappropriate for the occasion.

19. You fart while taking part in a group conversation.

20. You faint or get sick at the worst possible time.

21. An unflattering or compromising photo of you is widely distributed.

22. A family member brings up something private in front of friends.

23. You’re caught singing or dancing when you thought you were alone.

24. You eat something that was only meant for decoration.

25. You send an important email to important people with a truly unfortunate typo.


Now that I’ve finished the list, it occurs to me that at least one or two of these have happened to all of us. I hope this gave you some writing inspiration! If  you don’t want to miss future writing posts, follow the blog — you can sign up below. Happy writing!