Diabolical Would You Rather Conversation Starters
Updated February 17, 2026
Would you rather have fingers for toes or toes for fingers?
Would you rather only be able to whisper or only be able to shout?
Would you rather have a permanent clown smile or permanent sad puppy eyes?
Would you rather have to sing everything you say or dance everywhere you walk?
Would you rather always smell like onions or always taste like garlic?
Would you rather have uncontrollable hiccups during every job interview or uncontrollable flatulence during every first date?
Would you rather be forced to wear a clown wig every day or giant rubber boots every day?
Would you rather have your internal monologue spoken out loud for everyone to hear, or never be able to speak your thoughts at all?
Would you rather have a face that constantly looks angry or a face that constantly looks surprised?
Would you rather only be able to eat foods that are beige or only be able to drink liquids that are green?
Would you rather have your phone autocorrect every word to something inappropriate or randomly delete one photo every day?
Would you rather have a pet that hates you but lives forever, or a pet that loves you but only lives for one year?
Would you rather never be able to use emojis again or never be able to use punctuation again?
Would you rather have to narrate your life like a documentary or have a laugh track follow you everywhere?
Would you rather always feel like you need to sneeze but never can, or always feel like you need to yawn but never can?
Would you rather have every mirror you look into show you 10 years older or 10 years younger?
Would you rather be allergic to your favorite food or allergic to your favorite season?
Would you rather have a unibrow that grows an inch every day or ear hair that braids itself?
Would you rather have to relive the most embarrassing moment of your life every year or have it played on a loop at your funeral?
Would you rather be trapped in an elevator with someone who sings constantly or someone who hums the same tune over and over?
Would you rather lose your memory of the last five years or lose your ability to make new memories starting now?
Would you rather know exactly when you're going to die, or know exactly how you're going to die?
Would you rather be extremely successful at a job you hate, or struggle financially doing work you're passionate about?
Would you rather have everyone you know tell you the absolute truth all the time, or have them only tell you pleasant lies?
Would you rather be completely invisible to someone you love, or have them see you but completely misunderstand who you are?
Would you rather be able to read minds but never be able to turn it off, or be completely unable to understand what anyone is thinking or feeling?
Would you rather live in a world with no lies but also no privacy, or a world with complete privacy but where you can never be sure if anything anyone says is true?
Would you rather be forgotten by everyone you love, or have everyone you love forget everyone else and only remember you?
Would you rather be the one who suffers in every relationship you have, or be the one who causes suffering in every relationship you have but remain blissfully unaware of it?
Would you rather watch your dreams come true for someone else and have to pretend you're happy for them, or have your dreams come true but everyone thinks you don't deserve them?
Would you rather have unlimited power but be completely alone, or have deep connections with others but be powerless to help them when they suffer?
Would you rather know exactly what everyone thinks of you, or never know what anyone truly thinks of you?
Would you rather be incapable of feeling pain but also incapable of feeling love, or feel everything deeply including unbearable pain?
Would you rather be the most loved person in the world but unable to love anyone back, or be capable of deep love but completely unlovable to everyone?
Would you rather live forever but watch everyone you love die, or die young but be remembered forever?
Would you rather know the exact moment your partner will stop loving you, or know the exact reason they eventually will?
Would you rather be right but alone, or wrong but surrounded by people who love you?
Would you rather never experience jealousy again but also never experience passion, or feel passion intensely but be consumed by jealousy?
Would you rather be the one who always forgives but is never forgiven, or be the one who is always forgiven but can never forgive yourself?
Would you rather know exactly how many people truly love you, or know exactly how many people you've deeply hurt?
Would you rather save a stranger from dying but someone you love dies instead, or let the stranger die and your loved one lives, but you have to lie to them about it forever?
Would you rather be completely honest but everyone thinks you're lying, or be a compulsive liar but everyone believes everything you say?
Would you rather achieve everything you ever wanted but die alone and unloved, or live a long life surrounded by people who love you but never accomplish anything meaningful?
Would you rather know with certainty that there is no God, or know with certainty that God exists but He is indifferent to human suffering?
Would you rather betray your closest friend to save a stranger, or betray a stranger to save your closest friend, and have to live with whichever choice you made?
Would you rather erase one person from existence and no one remembers them, or save that person but erase yourself from their memory and everyone who knows you?
Would you rather save a thousand strangers by sacrificing one person you love, or save one person you love by letting a thousand strangers die, and have to live knowing you made a choice either way?
Would you rather have everyone you love die peacefully tomorrow, or live knowing you will outlive every single person you ever love by exactly 50 years?
Would you rather be completely forgotten within a year of your death, or be remembered forever for something you're deeply ashamed of?
Would you rather watch your child give up their greatest dream to care for you in old age, or watch them achieve their dream from a nursing home where you die alone?
Would you rather be able to see 10 years into your own future but be powerless to change anything, or be able to change anything but only 24 hours in advance?
Would you rather your deepest secret be revealed to everyone you know, or live knowing someone else's deepest secret that would destroy them if you ever told?
Would you rather die with a legacy of being good but having done nothing great, or die with a legacy of being great but having done unforgivable things?
Would you rather have your parents' approval but they fundamentally misunderstand who you are, or have them truly know you but never fully approve?
Would you rather be the person everyone comes to for help but no one helps when you're in need, or be the person who never helps others but is always supported when you fall?
Would you rather be able to undo one mistake you made but someone else has to suffer the consequences instead, or let your mistake stand but gain wisdom you could never have otherwise?
Would you rather never be able to say 'I love you' again, or never be able to hear it?
Would you rather have the power to end all suffering but lose your ability to feel compassion, or keep your compassion but be powerless to help?
Would you rather be remembered as a villain who was actually good, or as a hero who was actually evil?
Would you rather die knowing you were right about everything that mattered, or die knowing you were wrong but loved anyway?
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Would you rather have fingers for toes or toes for fingers?
Would you rather only be able to whisper or only be able to shout?
Would you rather have a permanent clown smile or permanent sad puppy eyes?
Would you rather have to sing everything you say or dance everywhere you walk?
Would you rather always smell like onions or always taste like garlic?
Would you rather have uncontrollable hiccups during every job interview or uncontrollable flatulence during every first date?
Would you rather be forced to wear a clown wig every day or giant rubber boots every day?
Would you rather have your internal monologue spoken out loud for everyone to hear, or never be able to speak your thoughts at all?
Would you rather have a face that constantly looks angry or a face that constantly looks surprised?
Would you rather only be able to eat foods that are beige or only be able to drink liquids that are green?
Would you rather have your phone autocorrect every word to something inappropriate or randomly delete one photo every day?
Would you rather have a pet that hates you but lives forever, or a pet that loves you but only lives for one year?
Would you rather never be able to use emojis again or never be able to use punctuation again?
Would you rather have to narrate your life like a documentary or have a laugh track follow you everywhere?
Would you rather always feel like you need to sneeze but never can, or always feel like you need to yawn but never can?
Would you rather have every mirror you look into show you 10 years older or 10 years younger?
Would you rather be allergic to your favorite food or allergic to your favorite season?
Would you rather have a unibrow that grows an inch every day or ear hair that braids itself?
Would you rather have to relive the most embarrassing moment of your life every year or have it played on a loop at your funeral?
Would you rather be trapped in an elevator with someone who sings constantly or someone who hums the same tune over and over?
Would you rather lose your memory of the last five years or lose your ability to make new memories starting now?
Would you rather know exactly when you're going to die, or know exactly how you're going to die?
Would you rather be extremely successful at a job you hate, or struggle financially doing work you're passionate about?
Would you rather have everyone you know tell you the absolute truth all the time, or have them only tell you pleasant lies?
Would you rather be completely invisible to someone you love, or have them see you but completely misunderstand who you are?
Would you rather be able to read minds but never be able to turn it off, or be completely unable to understand what anyone is thinking or feeling?
Would you rather live in a world with no lies but also no privacy, or a world with complete privacy but where you can never be sure if anything anyone says is true?
Would you rather be forgotten by everyone you love, or have everyone you love forget everyone else and only remember you?
Would you rather be the one who suffers in every relationship you have, or be the one who causes suffering in every relationship you have but remain blissfully unaware of it?
Would you rather watch your dreams come true for someone else and have to pretend you're happy for them, or have your dreams come true but everyone thinks you don't deserve them?
Would you rather have unlimited power but be completely alone, or have deep connections with others but be powerless to help them when they suffer?
Would you rather know exactly what everyone thinks of you, or never know what anyone truly thinks of you?
Would you rather be incapable of feeling pain but also incapable of feeling love, or feel everything deeply including unbearable pain?
Would you rather be the most loved person in the world but unable to love anyone back, or be capable of deep love but completely unlovable to everyone?
Would you rather live forever but watch everyone you love die, or die young but be remembered forever?
Would you rather know the exact moment your partner will stop loving you, or know the exact reason they eventually will?
Would you rather be right but alone, or wrong but surrounded by people who love you?
Would you rather never experience jealousy again but also never experience passion, or feel passion intensely but be consumed by jealousy?
Would you rather be the one who always forgives but is never forgiven, or be the one who is always forgiven but can never forgive yourself?
Would you rather know exactly how many people truly love you, or know exactly how many people you've deeply hurt?
Would you rather save a stranger from dying but someone you love dies instead, or let the stranger die and your loved one lives, but you have to lie to them about it forever?
Would you rather be completely honest but everyone thinks you're lying, or be a compulsive liar but everyone believes everything you say?
Would you rather achieve everything you ever wanted but die alone and unloved, or live a long life surrounded by people who love you but never accomplish anything meaningful?
Would you rather know with certainty that there is no God, or know with certainty that God exists but He is indifferent to human suffering?
Would you rather betray your closest friend to save a stranger, or betray a stranger to save your closest friend, and have to live with whichever choice you made?
Would you rather erase one person from existence and no one remembers them, or save that person but erase yourself from their memory and everyone who knows you?
Would you rather save a thousand strangers by sacrificing one person you love, or save one person you love by letting a thousand strangers die, and have to live knowing you made a choice either way?
Would you rather have everyone you love die peacefully tomorrow, or live knowing you will outlive every single person you ever love by exactly 50 years?
Would you rather be completely forgotten within a year of your death, or be remembered forever for something you're deeply ashamed of?
Would you rather watch your child give up their greatest dream to care for you in old age, or watch them achieve their dream from a nursing home where you die alone?
Would you rather be able to see 10 years into your own future but be powerless to change anything, or be able to change anything but only 24 hours in advance?
Would you rather your deepest secret be revealed to everyone you know, or live knowing someone else's deepest secret that would destroy them if you ever told?
Would you rather die with a legacy of being good but having done nothing great, or die with a legacy of being great but having done unforgivable things?
Would you rather have your parents' approval but they fundamentally misunderstand who you are, or have them truly know you but never fully approve?
Would you rather be the person everyone comes to for help but no one helps when you're in need, or be the person who never helps others but is always supported when you fall?
Would you rather be able to undo one mistake you made but someone else has to suffer the consequences instead, or let your mistake stand but gain wisdom you could never have otherwise?
Would you rather never be able to say 'I love you' again, or never be able to hear it?
Would you rather have the power to end all suffering but lose your ability to feel compassion, or keep your compassion but be powerless to help?
Would you rather be remembered as a villain who was actually good, or as a hero who was actually evil?
Would you rather die knowing you were right about everything that mattered, or die knowing you were wrong but loved anyway?