225+ ‘Regret’ Writing Prompts
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Make It or Break It
Write a letter from the perspective of an injured athlete to their younger self, warning about the injury and giving advice on how to avoid it.
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Streams of Memories
Write a monologue where an elderly character is reminiscing about their past, recalling both painful and joyous moments.
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The Unspoken Apology
Compose a monologue in which your character expresses regret and seeks forgiveness for a past action, something they can’t rectify.
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Spirit from the Sidelines
Write a story from the perspective of a ghost observing a day in the life of a busy family member.
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Ghostly Evocations
Pen a dialogue between a ghost and a human where the specter reveals pivotal moments from its past.
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The Final Transmission
Write about a character’s last moments in a spacecraft before a critical malfunction.
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Text Messages in a Bottle
Imagine you could send five text messages to a past or current important person in your life. What would you say?
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Tragic Tyrant
Pen down a story of a villain who was once a hero, or had the potential to be one, but was led astray.
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Dying Sun
Write about a vampire who desires to experience the sun one last time before their eternal slumber.
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Sorrow of the Undead
Write about a vampire who begins to experience regret for the things he can never have – a normal life, a family, growing old.
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Lost Love Rediscovery
Re-encounter an old love and describe how you both have changed since your relationship.
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The Lost Love Letter
Write a story about a love letter from many years ago that suddenly resurfaces on Valentine’s day.
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Voices From The Beyond
Craft a tale wherein a young medium tries to help spirits convey their unfinished businesses to their loved ones but one particular spirit refuses to move on.
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Haunting Regrets
Write about a significant regret or unfulfilled dream from your past that haunts you like a ghost.
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Unearthed Love Letters
An ancient, haunted love letter is found on Valentine’s Day, stirring the ghost of a heartbroken lover.
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One Last Letter
Craft a final letter that a passenger on Titanic pens to a loved one, knowing they won’t survive.
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Love Letters Unsent
Imagine finding an unsent love letter that you wrote in the past. Describe the person it was intended for and why you never sent it.
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Phantom of the Past
Write about a ghost that travels back in time to prevent its living past self from making a disastrous decision.
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Temporal Healing
Write about a protagonist who travels back in time to fix a regretful moment in their past.
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Time-Travel Paradigm
If you could travel back in time and change one event from your past, what would it be and why?
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Echoes of the Past
Place yourself in the rotting shoes of a former leader figure, now a zombie, surveying the rubble of the city that was once under your care.
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Survivor’s Guilt
Detail a survivor’s experience who left his famine-stricken village for a better life abroad.
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Choosing a Normal Life
Your superhero chooses to retire from their superhero life to live normally – write about their struggles and triumphs.
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Saving Self
Write a story revolving around a retired superhero battling personal demons in silent retirement.
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Releasing Regrets
Write about one regret you have from the past year, and then draft a plan for letting it go.
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Forgotten Correspondences
Imagine an abandoned house where letters never sent were kept stored away. Your main character accidentally stumbles upon them.
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Redemption Song
Detail the path of redemption Darth Vader takes towards the end of his life and how it changes the perception of his character.
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Lone Victory
Write a story in which the protagonist achieves their goal but loses something essential in the process.
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The Superhero’s Lost Love
Write about an aging superhero and a romantic relationship from their past that had to be sacrificed for the sake of humanity.
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The Letter Never Sent
Detail a letter you would write to someone you had feelings for but have lost contact.
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Last Wish Retribution
Create a narrative around a dying woman’s curse that brings forth a vengeful spirit, terrorizing those who didn’t fulfill her last wish.
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Asserting Your Boundaries
Write about a situation where you regret not setting proper boundaries and how you can set those now.
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Echoes from the Past
A cold case related to the detective resurfaces with renewed danger but a chance at redemption. How will they handle it?
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Lone Wolf Syndrome
The protagonist chose a solitary survival path, to avoid the pain of loss, only to find themselves wracked with guilt over those they could have helped.
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Late Bloomers
Craft a narrative about an individual who discovers their superhuman abilities late in life.
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Perspectives of the Conspirators
Pen a series of letters from the conspirators involved in Caesar’s assassination, written in the days leading up to and following the Ides of March.
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Shadow Player’s Endgame
Write a story about an aging spy who discovers a plot against their life and must outwit their own agency.
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Missed Opportunities
Reflect on a time when there was an opportunity to help someone during the Christmas season, but you didn’t take it. How would things change if you had chosen differently?
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The Queen’s Redemption
Imagine a storyline where the evil queen seeks redemption after attempting to kill Snow White.
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Flower Stand Monologues
Imagine that you run a small flower stand and create a monologue to your flowers at the end of the day.
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Missed Love Letters
Write about a series of love letters that never reached the beloved and how it changed their lives.
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Second Chances
Write about a moment in your life that you wish you could revise, and how you imagine things would be different now.
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Ghostly Guilt
Write about a mistake you made that still lingers in your consciousness, and how you have grown since then.
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The Apology Letter
Write about a character who writes a heartfelt apology to their former love interest.
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A Modern Marley’s Warning
Write a 21st-century version of Charles Dickens’ “A Christmas Carol”, focusing on the haunting visits Marley and the Christmas spirits pay to Scrooge.
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Letters To The Lost
Write a letter to the person you have lost, expressing all the things you wish you had said.
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Resolution Timeline
Describe a past regret or resolution that you had, how you worked through it, and where you stand today.
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Purgatorial Memories
Write a tale about a ghost who is stuck in purgatory, forced to relive its most traumatic human experiences.
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The Time Traveler
If you could go back and talk to your younger self or future self, what would you say?
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Tree of Forgiveness
Write about planting a ‘tree of forgiveness’ where each leaf represents a specific regret you have.
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Future Wisdom
Imagine meeting a future version of yourself. What advice would they give you about your regret?
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Map of Regrets
Draw a map of regrets you’ve had over your life, marking milestones of regret and ways you have overcome them.
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Courageous Conversations
Imagine having a conversation with someone or something involved in your regret and express your feelings, unanswered questions, and expectations.
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Releasing Regrets
Write a letter to yourself about a single regret you have, forgiving yourself for the mistake and exploring what you learned.
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The Disappointing Report Card
Describe a child’s reactions and actions after receiving a poor report card.
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Accidental Meeting
Write a story where the protagonist runs into an old classmate in an unexpected location.
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The Lost Love Letter
A forgotten love letter is found years later, rekindling old feelings and presenting an opportunity for a second chance at love.
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The Redemption Arch
Create a character starting from the depths of despair or wrongdoing, that slowly works their way towards redemption.
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Long Lost Letters
Discover a trove of letters from your younger self. What do they say, and how do they make you feel?
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Retrospective Apology
Write a monologue of a character apologizing to someone they can no longer reach.
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Room of Regret
Write about a lone room in the haunted mansion that has remained untouched and furnished.
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Tamed Eternity
Craft a story about a vampire who falls in love with a human, but refuses to turn them due to past regretful experiences.
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Evolution of Fear
Write about a main character who starts off disregarding the zombie threat, but soon comes to face the gruesome reality.
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Rewriting the Past Year
Imagine you have a time machine and you could rewrite any event of the past year, what would it be and how would it lead to a different present?
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Atoning for Misdeeds
Create a narrative about a character who’s seeking ways to make amends for a past action that caused emotional pain to someone they care for.
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Confronting Consumption
Write about a time you overlooked an eco-friendly option due to convenience or cost.
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The Turncoat’s Testimony
Write a monologue from the perspective of a person who caused heartbreak by ending a relationship, expressing their guilt and wavering doubt about their decision.
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Estranged Lover’s Lament
Craft a soliloquy where a character express their longing and regret towards an estranged lover.
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Echoes of Past Apps
Imagine a world where technology is advanced enough to capture and recreate ghost-like images of people’s past selves.
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Skiff’s End
Narrate the account of Jabba’s final moments during the Sarlacc pit incident, from his own perspective.
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Tragic Prologue
Pen a story that kicks off with the introduction of the villain, detailing their backstory or motive rather than starting with the protagonist.
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Final Redemption
Develop a story based on a protagonist striving to unravel a series of mysterious events, aiming to redeem their tragic past.
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Lost In A Moment
Write a story where the protagonist is trapped in a suspenseful situation because of a personal tragedy.
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Last Stand
Narrate the internal monologue of a Jedi in their final battle, facing their destiny with courage and acceptance.
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Crooning with Cupid
Imagine a song sung by Cupid, the god of love, about his adventures and misadventures on Valentine’s Day.
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Beyond the Lake
Envision a story where an uncharted lake serves as the portal to the afterlife, where the spirits of the deceased communicate with the living.
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Redemption Road
Create a villain who goes through significant character development and ends up seeking redemption.
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Echoes of the Lost Ship
Write about a famous shipwreck from history, with its crew said to still haunt the wreck site.
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Acceptance and Forgiveness
Write a letter to your broken heart, acknowledging its hurt and voicing forgiveness.
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The Hidden Kingdom Beneath the Gallows
Create a story revolving around an underground kingdom beneath the notorious gallows, inhabited by ghosts of the condemned men.
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A Ghost in the Lighthouse
Write a story about a ghost that warns sailors about an impending disaster from an abandoned lighthouse.
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Ghostly Repentance
A ghost haunts a place or person as a form of penance for a crime they committed in their primary life.
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The Unsent Valentine
Write a story where a character is desperate to confess their love but never sends their Valentine.
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A Letter Never Sent
Craft a story revolving around a heartfelt letter written in the throes of passion, but never delivered to the intended recipient.
