28 Writing Prompts about Regret

Hey there, fellow human!

Feeling bummed about stuff you did (or didn’t do)?

Well, guess what?

Everyone does! That’s why regret is such a great topic for spinning a story.

This prompt pack is all about those “what ifs” and “shoulda, woulda and couldas” that haunt us all.

We’ve got a bunch of ideas to get your creative juices flowing, whether you’re a short story ninja, a poetry pro, or an essay enthusiast.

Just breathe, spill your guts onto the page, and let the magic happen!

Writing Prompts about Regret

The Untaken Journey: Your protagonist was once presented with the opportunity to travel around the world, but chose not to because of responsibilities or fear. Now they regret not seizing this once-in-a-lifetime adventure. Develop a story where your protagonist finally decides to embark on this grand journey, proving it’s never too late to live one’s dreams.
An Apology Too Late: Your character has lived their life keeping a hurtful secret from someone close to them, a secret that could potentially shatter their bond. Now, on their deathbed, the character feels an overwhelming sense of regret and decides to reveal the truth. Write a heartfelt letter of confession and apology from the character to the person they wronged, expressing their deep regret and the reasons for their past actions.
Unfulfilled Aspirations: Imagine a character who always had a burning passion for something – music, painting, acting, writing – but due to circumstances, societal pressures, or fear of failure, they never pursued it. Now, in their old age, they are filled with regret for not following their heart when they had the chance. Develop a narrative where this character, despite their age, decides to chase their dream, showing it’s never too late to rectify a regret.
The Forgotten Friend: Your protagonist had a childhood best friend. As they grew older, however, life took them on different paths and they gradually lost touch. Years later, your protagonist learns about the tragic demise of their friend, and is filled with regret for not keeping the friendship alive. Construct a story where your protagonist finds a unique way to honour their lost friend, dealing with their regret and finding closure.
Ignored Advice: Your main character was given a piece of life-altering advice when they were young, but they dismissed it as trivial and continued down their chosen path. Over time, they realize the wisdom in those words and regret not heeding the advice. Write a story in which your character, with this newfound insight, attempts to amend their life according to the once-ignored advice.
The Unsaid Words: Imagine a scenario where your character and their significant other parted ways after an intense argument. They always thought there would be a chance to reconcile, to say all the things left unsaid, but that chance never came. Create a narrative where your character navigates their regret and learns how to move forward while carrying this weight.
Missed Goodbye: Your character’s loved one passed away suddenly, without giving them a chance to say goodbye or express their love one last time. The regret of not making the most of their final moments together haunts your character. Develop a story wherein your character finds solace and manages to say their belated goodbyes, albeit in a non-traditional way.
Forgone Forgiveness: The main character had a falling out with a family member and held onto their resentment for years. Now, that family member has passed away, leaving the character in a sea of regret for not forgiving them when they had the chance. Write a narrative where your character grapples with their regret and seeks a path towards forgiveness and self-healing.
The Love Not Chosen: Picture a character who once had to choose between two people they deeply loved. They made a choice but as time goes by, they start to question whether they chose correctly as they can’t help but feel regret for the love not chosen. Craft a story that follows this character’s journey as they come to terms with their choice and grapple with their lingering feelings.
A Career Over Family: Your character chose a demanding career over starting a family. While they achieved immense professional success, they find themselves feeling increasingly empty and regretful, longing for the family life they missed out on. Create a narrative that explores your character’s struggle with regret and their attempt to fill this void in their life.
The Neglected Passion: Imagine a character who, in their youth, had a passionate hobby. As they grew older, career and responsibilities took over, leaving no time for their passion. Now, they’re filled with regret for letting it go. Develop a story where this character rediscovers their passion, reminding readers that it’s never too late to reconnect with the things we love.
The Taken-for-granted Friend: Your character had a dependable friend who was always there for them. But they took this friend for granted, and over time, the friend walked away. Now, the character realizes their mistake and feels profound regret. Create a story that depicts your character’s attempts to mend this broken friendship and make amends.
Abandoned Homeland: Your protagonist left their homeland at a young age in pursuit of a ‘better life’. Over the years, as they fail to find a sense of belonging elsewhere, they regret leaving their roots. Your task is to write a story of your protagonist’s journey back to their homeland, seeking the connection they’ve longed for and addressing their regret.
The Unforgotten Betrayal: Your main character betrayed someone close to them in a moment of selfishness. Years later, this act of betrayal haunts them, filling them with guilt and regret. Write a narrative where your character seeks redemption and tries to right their past wrongs.
A Parent’s Regret: Your character was not always present for their children while they were growing up, prioritizing other aspects of life. As the children grow older and distance themselves, the character realizes their mistake and feels deep regret. Develop a story in which your character tries to rebuild these strained relationships and make up for lost time.
Neglected Health: The protagonist of your story neglected their health for years, prioritizing work, social life, and other aspects over their well-being. After a significant health scare, they are filled with regret. Create a story that follows your character’s journey towards a healthier lifestyle, aiming to inspire readers to prioritize their health before it’s too late.
The Unfinished Book: Imagine a character who started writing a book in their early 20s, full of passion and ideas. As time passed, their priorities shifted and the book was left unfinished. Now in their later years, they regret never completing it. Craft a narrative where your character decides to complete their long-abandoned book, showing it’s never too late to fulfill a dream.
The Lost Mentor: Your character had a mentor who always believed in them, but due to pride and misunderstanding, they parted ways on bad terms. Years later, they regret not mending things when they had the chance. Develop a story where your character attempts to reconcile with the past and pay tribute to their lost mentor.
An Unkept Promise: The protagonist once made a promise to a loved one but failed to keep it. This unkept promise haunts them with regret. Your task is to write a story that explores how the character finally finds a way to fulfill the long overdue promise, or comes to terms with their inability to do so.
The High School Dropout: Your main character dropped out of high school and led a life full of struggles. Now in their adulthood, they regret their decision and long for a different life. Create a story that follows your character’s journey back to education, demonstrating the power of perseverance and the courage to confront regrets.
The Estranged Sibling: Your protagonist had a falling out with their sibling over a trivial matter, and they haven’t spoken in years. After hearing news of their sibling’s achievements, they are filled with regret for the lost relationship. Develop a narrative where your protagonist reaches out to their estranged sibling, seeking reconciliation and healing.
The Missed Opportunity to Help: The main character had the chance to help someone in need but chose not to, for some reason. Later, they learn the person fell into greater hardship, and they regret not lending a helping hand when they had the chance. Write a story in which the character grapples with their regret and seeks a way to make amends.
The Ignored Intuition: Your character once had a strong gut feeling about a decision but ignored it, leading to an outcome they now regret. Craft a narrative that explores your character’s journey to trust their intuition again, learning from their past mistakes.
The Hasty Marriage: Your protagonist married in haste, under societal or familial pressure. As years pass, they realize they are not truly happy and regret not taking the time to understand their partner better before committing. Develop a story where your protagonist confronts their regret, either by trying to mend their relationship or seeking happiness elsewhere.
The Last Place Home: Imagine a character who, desperate to break free, leaves their small town at a young age. Over the years, they have grown to miss the simplicity and sense of community they once had. They now regret their haste to leave. Craft a narrative in which your character decides to revisit their hometown, facing their past, and understanding their true feelings about ‘home’.
The Given Away Heirloom: Your protagonist inherited a precious heirloom from their grandparent. However, in their youth and ignorance, they sold it. Now older and wiser, they regret their decision and miss the connection to their roots. Develop a story in which the character embarks on a journey to reclaim the lost heirloom, reconnecting with their past along the way.
The Regret of Dishonesty: Your main character lied to their partner about something significant, thinking it would save their relationship. However, the guilt of this lie eventually drove them apart. Now, the character deeply regrets their dishonesty. Write a narrative in which your character tries to win back their partner’s trust, demonstrating the importance of honesty in relationships.
The Lost Art of Letter Writing: In the age of technology, your character regrets losing touch with the old-fashioned art of letter writing. They miss the personal touch and the deeper emotional connection that handwritten letters provide. Create a narrative where your character decides to bring back this lost art in their life and inspires others around them to do the same.