Free Creative Writing Prompts #61: Regrets

1. Talk about the biggest regret you've had in your entire life. What led up to this occurring and what was the aftermath? What have you learned from this situation and how have you applied it to what you do now?

2. Do a character study on a person who uses his regrets to guide most of the decisions he makes in his life. What would happen to this person if he was able to move on free of these past transgressions?

3. What is one way that you have dealt with the regrets in your life? Do you just let them go easily or does it take a lot of talking and time? Have you needed to get professional help? Discuss the entire process for working regret out of your system.

4. What would you do if you could reverse one major regret from your past? How do you think your life would change if this was erased and how would it affect you as a person? Was it really all that much of an impact?

5. Go back in your mind to a conversation that you wish had not gotten so emotional and change it into a logical discussion on your part. Word for word, alter what was said and turn it into an empathic and emotional discourse. How does it change and what is the end result?

6. You have been given one last day with the "one that got away." What do you do with this time, what do you say, and what do you do? You only have this one last chance, so make it count.

7. Imagine that you have had a negative conversation with a person who passed away before you were able to make up. Write about the situation and your attempts to communicate with this person beyond the grave.

8. Write down a plan for your future financial situations based on the poor decisions that you have made in the past. Instead of regretting these past problems, try to look at them as opportunities to move forward with this new knowledge.

9. Craft a story about a kid who made a mistake in elementary school that cost him his popularity through middle and high school. Then give him an opportunity to go back and change that mistake. He can then choose between these two paths for the rest of his life. What path does he choose and why?

10. Have you ever caused extreme harm to someone without knowing it and then found out years later about what was said or done? If so, write about that experience, if not, create a story in which someone from your past comes up to confront you about said past issue.


While there are many things that I could regret in my life, it's hard to when I take into account how much I learned from those situations. Many things that I regret from high school involve me being socially awkward. As a result of those experiences, however, I learned to be a lot more socially adept and at this point I feel like I can communicate with people from most walks of life. Hopefully, these free creative writing prompts about your regrets can make you feel a similar way. If you're feeling brave, feel free to use the space below to provide your writing response to one of these prompts. Happy writing!


Bonus Prompt - Create a giant chart of all the major regrets of your life and write a story in which you rectify all of these wrongs. It's sort of like the show "My Name is Earl." Go into detail and try to fix everything from childhood through adulthood.

Write from one of these inspiring prompts!

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