Dare to Choose? 100 Diabolical Would You Rather Questions That Will Twist Your Mind

Diabolical Would You Rather Questions aren’t your average easy-peasy choices. They throw you into the deep end of moral dilemmas, force you to confront your fears, and often leave you questioning everything you thought you knew. Get ready for some seriously tough decisions!

What Makes a “Diabolical Would You Rather” So Diabolical?

So, what exactly makes a Would You Rather question “diabolical”? It’s all about the options presented. These aren’t simple preference questions like “Would you rather have pizza or tacos?”. Instead, they present two undesirable outcomes, forcing you to pick the lesser of two evils, or make a choice that reveals something unexpected about your values. They can be morbid, embarrassing, or just plain bizarre, but the one thing they all have in common is that they are HARD. They reveal the core of who you are.

The popularity of these questions comes from their ability to spark conversations and debates. They’re great for breaking the ice, filling awkward silences, or just getting to know people on a deeper level. Think about it: you can learn a lot about someone based on whether they’d rather fight 100 duck-sized horses or one horse-sized duck!

  • Ice Breakers: Fun for Parties
  • Deep Thinking: Reveals Personal Values
  • Conversation Starters: Sparks Debate

How are Diabolical Would You Rather questions used? Well, pretty much anywhere! Games at parties, road trip entertainment, team-building exercises, or even just a fun way to pass the time with friends. They are often used to test people’s limits and see how they react under pressure. These questions can also be great for creative writing prompts or even therapy, helping people explore their feelings and values in a safe and engaging way.

Usage Description
Parties Icebreaker and entertainment
Road Trips Keeps passengers engaged

Mind-Bending Moral Dilemmas

  1. Would you rather save a group of strangers or your own family from a burning building?
  2. Would you rather know the date of your own death or the cause of it?
  3. Would you rather have the ability to read minds but be unable to turn it off, or be completely invisible but only when no one is looking directly at you?
  4. Would you rather be falsely accused of a crime and sentenced to prison, or get away with a crime but live with the guilt?
  5. Would you rather have unlimited wealth but be unable to ever experience love, or have true love but live in poverty?
  6. Would you rather lose the ability to lie or believe everything you’re told?
  7. Would you rather cause the death of one innocent person to save ten guilty ones, or let the ten guilty ones die?
  8. Would you rather have the power to bring back one person from the dead, knowing someone else will die in their place, or leave things as they are?
  9. Would you rather know all the secrets of the universe but be unable to share them, or know nothing but be able to convince anyone of anything?
  10. Would you rather be immortal but alone, or live a normal lifespan with the love of your life?
  11. Would you rather be able to stop time but only for 10 seconds a day, or have the ability to rewind time by 5 seconds every hour?
  12. Would you rather be the smartest person in the world and always be misunderstood, or be of average intelligence and always be accepted?
  13. Would you rather live in a world where everyone is perfectly honest but brutally cruel, or a world where everyone is kind but always lying?
  14. Would you rather have the power to heal any injury but only if you take the same injury upon yourself, or have the power to teleport but only to places you’ve already been?
  15. Would you rather live in a society with no rules but constant chaos, or a society with strict rules and no freedom?
  16. Would you rather always say exactly what’s on your mind, no matter the consequences, or never be able to express your true feelings?
  17. Would you rather win the lottery but lose all your friends, or stay poor but maintain your friendships?
  18. Would you rather know the answer to every question but forget everything you’ve ever learned, or remember everything but never learn anything new?
  19. Would you rather have the power to control the weather but only for a small area, or have the power to control animals but only one species at a time?
  20. Would you rather live in a world where all your dreams come true but everyone else suffers, or a world where no one’s dreams come true but everyone is happy?
  21. Would you rather always be right but never be believed, or always be wrong but always be trusted?
  22. Would you rather have the power to change the past but risk altering the present, or have the ability to see the future but be unable to change it?
  23. Would you rather be famous and hated, or unknown and content?
  24. Would you rather be considered a genius but secretly be an idiot, or be considered an idiot but secretly be a genius?
  25. Would you rather live for a year as the opposite sex, or lose a year of your life?
  26. Would you rather have the perfect memory, but never be able to forget anything, or have a terrible memory, but never remember embarrassing moments?
  27. Would you rather be completely alone for the rest of your life, with all the resources you need, or live in a crowded city, but be completely ignored by everyone?
  28. Would you rather be forced to watch your favorite movie every day for the rest of your life, or never be able to watch it again?
  29. Would you rather always have a song stuck in your head, but it’s always a terrible song, or never be able to listen to music again?
  30. Would you rather have the ability to talk to animals, but they only tell you their darkest secrets, or be able to understand plants, but they constantly complain about the weather?
  31. Would you rather live in a world where everyone is happy and content, but there is no innovation or progress, or a world where there is constant innovation and progress, but everyone is miserable?
  32. Would you rather have the ability to control your dreams, but be unable to distinguish them from reality, or never be able to dream again?
  33. Would you rather be the hero everyone loves, but secretly be corrupt, or be the villain everyone hates, but secretly be doing good?
  34. Would you rather have an unlimited supply of your favorite food, but it’s the only thing you can ever eat, or never be able to eat your favorite food again?
  35. Would you rather have the power to make anyone fall in love with you, but you can’t control who they are, or never be able to fall in love again?

Gross and Gruesome Choices

  • Would you rather eat a plate of toenail clippings or drink a glass of earwax?
  • Would you rather have to smell burnt hair for the rest of your life or taste pennies every time you drink water?
  • Would you rather have a permanent wedgie or a permanent booger hanging out of your nose?
  • Would you rather lick a public toilet seat or swim in a pool of vomit?
  • Would you rather chew on a dirty diaper or swallow a handful of spiders?
  • Would you rather wear a diaper full of mashed potatoes for a day or wear a shirt soaked in vinegar?
  • Would you rather shave all your hair off or never be able to cut your nails again?
  • Would you rather have teeth made of jelly or fingernails made of cheese?
  • Would you rather be covered in slugs or have ants crawling all over you?
  • Would you rather have a permanent itch you can’t scratch or a permanent sneeze you can’t release?
  • Would you rather pick your nose in public every day for the rest of your life or never be able to shower again?
  • Would you rather have a permanent fart that smells like rotten eggs or a permanent burp that sounds like a foghorn?
  • Would you rather have a hairy tongue or a slimy scalp?
  • Would you rather have constantly sweaty palms or constantly dry eyes?
  • Would you rather eat a bug sandwich or drink a glass of spoiled milk?
  • Would you rather have to wear socks with sandals everywhere you go or wear a speedo to a funeral?
  • Would you rather have worms for hair or have spiders for teeth?
  • Would you rather have to smell dog food for the rest of your life or have to eat cat food for a week?
  • Would you rather wear wet socks all day every day or have a rock in your shoe that you can’t remove?
  • Would you rather have to drink a glass of your own sweat every morning or eat a hairball every night?
  • Would you rather have permanently yellow teeth or permanently green hair?
  • Would you rather have to clean public restrooms for a living or clean up after a zoo animal?
  • Would you rather have to eat a live cockroach or kiss a dead frog?
  • Would you rather have your skin peel off every time you go outside or have your hair fall out every time you get stressed?
  • Would you rather have to smell your own feet for the rest of your life or never be able to taste food again?
  • Would you rather have to sleep in a coffin every night or wake up covered in cockroaches every morning?
  • Would you rather have to pluck out all your eyelashes or pull out all your nose hairs?
  • Would you rather have to wear a clown costume every day for the rest of your life or have to sing opera in public every time you sneeze?
  • Would you rather have to eat a plate of raw onions every day or have to drink a gallon of pickle juice every week?
  • Would you rather have to lick the bottom of your shoe or chew on a used toothbrush?
  • Would you rather have to use a public restroom that hasn’t been cleaned in a month or have to change a baby’s diaper on an airplane?
  • Would you rather have to eat a bowl of mayonnaise every day or have to drink a cup of hot sauce every week?
  • Would you rather have to smell like garbage for the rest of your life or have to look like a garbage man?
  • Would you rather have to wear a full suit of armor in the summer or wear a bikini in the winter?
  • Would you rather have to shave your eyebrows every day for the rest of your life or have to wax your legs every week?

Uncomfortable Social Situations

  1. Would you rather accidentally send a text meant for your crush to your mom, or accidentally call your boss “mom”?
  2. Would you rather show up to a formal event in casual clothes or show up to a casual event in formal clothes?
  3. Would you rather be caught singing loudly and off-key in public or trip and fall in front of a crowd of people?
  4. Would you rather have your pants rip open in the middle of a presentation or spill coffee all over your boss?
  5. Would you rather have to give a speech naked or have to sing the national anthem backwards in front of a large crowd?
  6. Would you rather accidentally insult your idol or accidentally compliment your worst enemy?
  7. Would you rather forget your best friend’s birthday or forget your anniversary?
  8. Would you rather be stuck in an elevator with your ex or stuck in an elevator with someone who talks nonstop about conspiracy theories?
  9. Would you rather accidentally like a really old and embarrassing post on your crush’s social media or accidentally send a risqué text to your grandma?
  10. Would you rather be known for always telling bad jokes or always having food stuck in your teeth?
  11. Would you rather have to dance in front of a crowd of strangers or have to give a presentation on a topic you know nothing about?
  12. Would you rather accidentally walk into the wrong bathroom or accidentally call someone by the wrong name multiple times?
  13. Would you rather have your credit card declined in front of a long line of people or have your fly down during an important meeting?
  14. Would you rather be caught cheating on a test or be caught gossiping about someone behind their back?
  15. Would you rather have to wear a funny hat everywhere you go or have to wear mismatched shoes?
  16. Would you rather accidentally interrupt a wedding or accidentally crash a funeral?
  17. Would you rather have to apologize to someone you hate or have to ask for help from someone you dislike?
  18. Would you rather be the subject of an embarrassing meme or have your embarrassing moment go viral?
  19. Would you rather have to live with your parents forever or have to live in a haunted house?
  20. Would you rather be the worst player on a winning team or the best player on a losing team?
  21. Would you rather have to sing karaoke with a stranger or have to dance with your grandma at a party?
  22. Would you rather be known for always being late or always interrupting people?
  23. Would you rather have to explain a bad joke to someone who didn’t understand it or have to pretend to like a terrible gift?
  24. Would you rather be forced to go on a blind date with someone you find incredibly unattractive or have to attend a family reunion with relatives you can’t stand?
  25. Would you rather have to wear a name tag everywhere you go or have to introduce yourself to everyone you meet?
  26. Would you rather be caught snooping through someone’s drawers or be caught eavesdropping on a private conversation?
  27. Would you rather have to write an apology letter to someone you don’t feel sorry for or have to accept an apology from someone you don’t forgive?
  28. Would you rather be the victim of a harmless prank or the perpetrator of a failed prank?
  29. Would you rather have to ask a stranger for help with something embarrassing or have to witness a stranger’s embarrassing moment?
  30. Would you rather be the subject of a roast or have to give a toast at a wedding?
  31. Would you rather be forced to watch a reality TV show every day for the rest of your life or have to participate in a reality TV show?
  32. Would you rather have to wear a sandwich board with an embarrassing message on it or have to carry a sign advertising a product you hate?
  33. Would you rather be caught lying about your age or be caught exaggerating your accomplishments?
  34. Would you rather have to explain your embarrassing childhood nickname to your new boss or have to introduce your eccentric family to your significant other?
  35. Would you rather have to give a presentation in a language you don’t speak or have to perform a stand-up comedy routine in front of a live audience?

Diabolical Would You Rather Questions are more than just games. They’re windows into our souls, revealing our values, fears, and sense of humor. So next time you’re looking for a way to spice up a conversation, pull out a few of these questions and get ready for some unexpected and unforgettable answers!