Medium NaNoWriMo Writing Prompt #3

What is your character’s biggest regret?

In honor of National Novel Writing Month 2016, Medium is offering a weekly writing prompt now through the beginning of December to spark your imagination and help you write fifty thousand words in November.

Last week’s post was about building a backstory. This week is about taking that backstory and adding darkness.

Epic facepalm

Deep down, we all have something we wish we would have done, or wouldn’t have done.

  • What haunts your character?
  • What do they resent and why?
  • How might your character be granted a second chance at something?
  • How can you use a decision the character made in your novel to backfire on them later?
  • How can you use a regret to push your character to change?

In my NaNoWriMo 2014 Novel, When Desperation Meets Opportunity, my character Jim tells his story alongside another person, Maggie. Both parties are being coerced into doing different tasks for a mystery person. Throughout the story, there are allusions from Maggie’s side about the father of her baby leaving her. Then, in Chapter 17, the dots are connected, and it is revealed that Jim is the father. His regret from taking off the moment he knew she was pregnant only intensifies as he learns the reasons why she shows up at his door (the child has been abducted!). The ramifications of this regret are a strong driving force as the story winds its way to a conclusion.

You can read the full scene here.


Whether it is a big bomb like the reappearance of a past love interest or something subtle that carries through a chapter, how can you use the regrets of your characters to expand your plot or provide important context for their personalities?

We’d love it if you would share the deepest regret of your main character as a response below. You could share the actual draft text and/or comment on what you discovered by way of this prompt. However, if you don’t feel quite comfortable going public with some juicy drama, click on the recommend heart so at least we know this inspired you!

Keep writing, ‘WriMos!

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