300 Hard Would You Rather Questions to Break Your Friends' Brains

"Would you rather" questions are great ways to put your brain in a bind and, ultimately, to make you feel extremely grateful that you (probably) don’t actually have to answer any of these questions in real life. They’re also excellent ways to examine your partner's or your friends’ values as well as your own. 

Of course, not all of these types of questions are created equal. Sometimes, these quandaries can be heartwarming choices between two great options. Other times, they can be agonizingly difficult nightmare scenarios. Almost always, they're amazing ways to start conversations and get to know yourself and the people around you a little better.

Would you rather have another boring, run-of-the-mill conversation or a hilarious, deep, and revealing chat inspired by one of these "would you rather" questions? We bet we know the answer! These 300 questions explore everything from historical quandaries to big questions about life and death.

Some are harder than others, but all are sure to put your imagination to work...and if you ever do find yourself in a situation where you have to decide between knowing how you die and when you die, or whether you'd choose the Overlook Hotel or the Bates Motel, you'll know what to do.

1. History Would You Rather Questions
2. Nature and the Body Would You Rather Questions
3. Geography and Travel Would You Rather Questions
4. Movies, TV, and Book Would You Rather Questions
5. Food and Everyday Life Would You Rather Questions
6. Truly Difficult Would You Rather Questions

History Would You Rather Questions

Would you rather be a royal a century ago, or a regular person today?

Would you rather witness the signing of the Declaration of Independence or the fall of the Berlin Wall?

Would you rather spend one year as a medieval knight or a Renaissance artist?

Would you rather attend the first Olympic Games in ancient Greece or the first modern Olympics in 1896?

Would you rather explore the Library of Alexandria before its decline or see a show at the original Globe Theatre?

Would you rather have a portrait of you painted by Leonardo da Vinci or Michelangelo?

Would you rather spend a week at Versailles during the reign of Louis XIV or at Buckingham Palace during the Victorian era?

Would you rather sail with Christopher Columbus in 1492 or travel with Lewis and Clark in 1804?

Would you rather watch the construction of the Great Pyramid of Giza or the building of Stonehenge?

Would you rather attend a Roman gladiator contest or a medieval joust?

Would you rather have dinner with Cleopatra or Julius Caesar?

Would you rather live through the Roaring Twenties or the Summer of Love?

Would you rather witness the Wright brothers' first flight or the Apollo 11 moon landing?

Would you rather explore a perfectly preserved Viking settlement or a perfectly preserved Roman city?

Would you rather spend a day in 18th-century London or 18th-century Paris?

Would you rather have dinner with Benjamin Franklin or George Washington?

Would you rather discover a lost ancient civilization or a previously unknown species?

Would you rather be transported to 1920 or 2120?

Would you rather experience the 1969 Woodstock festival or the 1985 Live Aid concert?

Would you rather own an original Gutenberg Bible or an original Shakespeare First Folio?

Would you rather live in New York City in 1900 or Los Angeles in 1950?

Would you rather spend a week aboard the Titanic before its maiden voyage or the Mayflower during its voyage to America?

Would you rather visit the original Seven Wonders of the Ancient World or attend every World's Fair from 1851 onward?

Would you rather have the chance to meet any famous person who is alive today or any famous person from history?

Would you rather know the exact location of Atlantis or solve the mystery of the Voynich manuscript?

Would you rather visit a fully reconstructed medieval castle or a fully reconstructed ancient city?

Would you rather be a newspaper reporter during the moon landing or during the sinking of the Titanic?

Would you rather spend a month in Victorian London or Belle Époque Paris?

Would you rather own a surviving artifact from ancient Greece or ancient Rome?

Would you rather know exactly what happened to Amelia Earhart or what happened to the Roanoke colonists?

Would you rather attend the first performance of a Shakespeare play or the premiere of a Beethoven symphony?

Would you rather be transported to prehistoric Earth or 10,000 years into the future?

Would you rather see a dinosaur alive or a woolly mammoth alive?

Would you rather explore an ancient Egyptian tomb or a Viking burial ship?

Would you rather live in a city with perfectly preserved historical architecture or one with buildings designed entirely by future architects?

Would you rather spend a day as a Victorian child or a Victorian adult?

Would you rather visit ancient Athens at its height or Renaissance Florence at its height?

Would you rather own Napoleon's hat or Abraham Lincoln's stovepipe hat?

Would you rather witness the first printing of a newspaper or the first broadcast of a television program?

Would you rather spend a year as an explorer in the 1800s or an astronaut in the 2200s?

Would you rather know the true identity of Jack the Ripper or the real purpose of Stonehenge?

Would you rather tour the White House in 1800 or the White House 200 years in the future?

Would you rather attend a royal coronation in medieval Europe or one in the modern era?

Would you rather visit every U.S. state as it existed in 1900 or every state as it will exist in 2100?

Would you rather own an original map drawn by an ancient civilization or a map of Earth 1 million years in the future?

Would you rather spend one day in a perfectly recreated 1950s town or a perfectly recreated 1750s town?

Would you rather know the identity of every person buried in an unmarked historical grave or every person who lived in a vanished city?

Would you rather uncover a lost Shakespeare play or a lost Beethoven composition?

Would you rather be the only person to photograph a famous historical event or the only person to film it?

Would you rather rewrite one event in history or know exactly how one major future event will unfold?

Nature and the Body Would You Rather Questions

Would you rather have to wear wet socks every day of your life or have to wear winter clothes over your hands for the rest of your life?

Would you rather communicate with whales or elephants?

Would you rather have hair for teeth or teeth for hair?

Would you rather have perfect knowledge of the human brain or the human genome?

Would you rather discover a new planet or a new species on Earth?

Would you rather visit the deepest part of the ocean or the surface of Mars?

Would you rather have a pet dinosaur or a pet mammoth?

Would you rather know exactly how the universe will end or exactly how life on Earth will end?

Would you rather be able to see 100 years into the future or 1000 years into the past?

Would you rather witness a total solar eclipse every year or a total lunar eclipse every month?

Would you rather have night vision or echolocation?

Would you rather live in a world without insects or a world without reptiles?

Would you rather be able to instantly identify every plant or every animal?

Would you rather explore the ocean beneath Antarctica or the underground caves beneath the Amazon?

Would you rather discover evidence of extraterrestrial microbial life or intelligent extraterrestrial life?

Would you rather be able to hibernate for six months or never need to sleep?

Would you rather have the strength of a gorilla or the speed of a cheetah?

Would you rather understand every language spoken by humans or every form of animal communication?

Would you rather watch evolution happen over millions of years or witness Earth's formation?

Would you rather visit the center of Earth if it were completely safe or travel to the edge of the observable universe?

Would you rather have perfect memory or perfect spatial awareness?

Would you rather be able to control your body temperature or your heart rate?

Would you rather discover a cure for one major disease or a way to slow human aging?

Would you rather know exactly how many species will go extinct in the future or how many have gone extinct in the past?

Would you rather live alongside dinosaurs for one year or explore the Earth 100 million years from now?

Would you rather have the ability to regenerate like a starfish or withstand extreme temperatures like a tardigrade?

Would you rather swim with a giant squid or fly alongside an albatross?

Would you rather explore the Mariana Trench or the largest cave system on Earth?

Would you rather be able to grow plants instantly or purify polluted water instantly?

Would you rather experience zero gravity for a year or live underwater for a year?

Would you rather have perfect eyesight or perfect hearing?

Would you rather know what dreams really are and why humans dream, or exactly what every dream means?

Would you rather discover a second Earth orbiting another star or prove that time travel is possible?

Would you rather see the Earth from the Moon or see the Moon from Mars?

Would you rather be able to survive without oxygen for an hour or without food for a month?

Would you rather control the weather within a one-mile radius or predict the weather perfectly?

Would you rather have perfect control over your body or perfect control over your emotions?

Would you rather be able to shrink to the size of an ant or grow to the size of a giraffe?

Would you rather have a photographic memory or be able to forget anything you choose?

Would you rather be able to detect every lie or every illness?

Would you rather be a hummingbird or a tortoise?

Would you rather discover a new fundamental force of nature or a new dimension?

Would you rather see the world through the eyes of a bee or a shark?

Would you rather have stiletto high heels on your feet permanently, or feet for hands?

Would you rather know how the universe was created or how it will end?

Would you rather travel through the inside of a glacier or a volcano, assuming both were completely safe?

Would you rather be able to communicate telepathically with one animal species or one group of humans?

Would you rather live in a world where gravity is half as strong or twice as strong?

Would you rather have an extra pair of arms or an extra pair of eyes?

Would you rather witness the birth of a star or the collision of two galaxies?

Geography and Travel Would You Rather Questions

Would you rather permanently live on a remote island or in the middle of a huge city?

Would you rather visit every country in the world or every U.S. national park?

Would you rather cross the Sahara by camel or Antarctica by dogsled?

Would you rather live beside the ocean or beside a mountain range?

Would you rather spend a week camping (with proper gear) at the coldest place or the hottest place in the world?

Would you rather spend a month in Tokyo or Paris?

Would you rather take a road trip across every U.S. state or a train trip across Europe?

Would you rather win a free trip to the Amazon rainforest or the Arctic tundra?

Would you rather live permanently in a houseboat or a lighthouse?

Would you rather spend a night alone in an isolated desert or an isolated forest?

Would you rather visit a country with no rivers or a country with no trees?

Would you rather be able to teleport anywhere on Earth or fly anywhere on Earth?

Would you rather live permanently in summer or permanently in winter?

Would you rather travel only by train or only by ship for the rest of your life?

Would you rather visit every capital city or every UNESCO World Heritage site?

Would you rather have to visit all the world's largest caves or its largest waterfalls?

Would you rather live above the Arctic Circle or below the Antarctic Circle?

Would you rather successfully climb Mount Everest or journey to the bottom of the Marianus Trench in a submersible?

Would you rather visit the world's most remote inhabited place or its most remote uninhabited place?

Would you rather spend your honeymoon at a desert oasis or a rainforest treehouse?

Would you rather have to travel without a cellphone or without a suitcase?

Would you rather cross the Atlantic on a 19th-century sailboat or a modern cruise ship?

Would you rather visit every place mentioned in your favorite book or every place featured in your favorite movie?

Would you rather have a home overlooking a volcano or a glacier?

Would you rather explore the ruins of Pompeii or Machu Picchu?

Would you rather travel around the world without flying or without using motor vehicles?

Would you rather live in a city where it rains every day or one where it never rains?

Would you rather spend a month on the edge of a volcano or on the edge of a sinkhole?

Would you rather visit every island in the Caribbean or every island in the Mediterranean?

Would you rather explore the world's longest river or deepest lake?

Would you rather be stranded for a year alone on a tropical island or in a mountain cabin?

Would you rather visit every U.S. state capital or every national capital in Europe?

Would you rather spend a week in a medieval European town or a futuristic Asian city?

Would you rather take a 30-hour train ride or a 14-hour flight?

Would you rather live in a city with no cars or a city with no skyscrapers?

Would you rather bungee jump or leap off the top of the world's tallest waterfall into deep water?

Would you rather cross the United States on foot or bicycle?

Would you rather live in a country where the sun never fully sets or never fully rises?

Would you rather have unlimited free hotel stays or unlimited free airfare?

Would you rather explore every major desert or every major rainforest?

Would you rather visit a city founded more than 2000 years ago or one founded within the past 50 years?

Would you rather suddenly gain ownership of Alaska or Patagonia?

Would you rather visit a family member from 500 years in the past or 500 years in the future?

Would you rather be the honored guest of every leader from history or of every current world leader?

Would you rather live in a city where everyone is banned from walking or driving?

Would you rather explore a country entirely by car or entirely by public transportation?

Would you rather sleep under the Northern Lights or beneath a total solar eclipse?

Would you rather visit every continent once or one continent 20 times?

Would you rather live at sea level or 10,000 feet above sea level?

Would you rather be able to have an encyclopedic knowledge of geography or history?

Movies, TV, and Book Would You Rather Questions

Would you rather live in the world of Harry Potter or The Lord of the Rings?

Would you rather spend a week on the set of your favorite movie or inside the fictional world of it?

Would you rather know every alternate ending ever filmed or watch every deleted scene ever shot?

Would you rather meet your favorite fictional character or the actor who plays them?

Would you rather own the original screenplay of your favorite movie or an original prop from it?

Would you rather watch only movies made before 1980 or after 2020?

Would you rather be trapped in a mystery novel or a science-fiction novel?

Would you rather have a library containing every book ever published or a movie theater containing every film ever made?

Would you rather live in a sitcom or a prestige drama?

Would you rather be the protagonist in a horror movie or the villain in an action movie?

Would you rather know the ending of every unfinished TV series or every unfinished book series?

Would you rather have dinner with your favorite author or favorite director?

Would you rather watch one perfect movie for the rest of your life or read one perfect book?

Would you rather live in The Simpsons or Bob's Burgers?

Would you rather be Sherlock Holmes or Hercule Poirot?

Would you rather spend a day at Hogwarts or Jurassic Park?

Would you rather survive a zombie movie or a disaster movie?

Would you rather have a magical wardrobe like the one in The Chronicles of Narnia or a time machine?

Would you rather be transported into a Wes Anderson movie or a Tim Burton movie?

Would you rather live in a classic black-and-white movie or a modern blockbuster?

Would you rather know the title of every movie that will win an Oscar for the next 50 years or every book that will become a bestseller?

Would you rather own the original Batmobile or the DeLorean from Back to the Future?

Would you rather spend one year as a character in Star Trek or Star Wars?

Would you rather be the detective in a murder mystery or the villain in a thriller?

Would you rather watch every movie ever made but never read another book, or read every book ever written but never watch another movie?

Would you rather have the ability to enter any fictional world or bring one fictional character into reality?

Would you rather attend the premiere of a movie destined to become a classic or watch it privately with its director?

Would you rather know the true ending of The Sopranos or the true identity of Banksy?

Would you rather live in Downton Abbey or The Office?

Would you rather be a wizard or a superhero?

Would you rather have a personal library designed like the one in Beauty and the Beast or the Batcave?

Would you rather read a new novel by your favorite author every year or watch a new film by your favorite director every year?

Would you rather spend a month in a fantasy kingdom or a science-fiction space station?

Would you rather be the narrator of a documentary series or the host of a late-night talk show?

Would you rather know every movie's original working title or every famous actor's rejected role?

Would you rather live in a world without horror movies or romantic comedies?

Would you rather be able to pause any movie or rewind real life by 10 minutes?

Would you rather own a signed first edition of your favorite book or a movie prop worth the same amount?

Would you rather play the hero in a superhero movie or the villain everyone remembers?

Would you rather discover a lost episode of your favorite TV show or an unpublished novel by your favorite author?

Would you rather have the powers of Superman or the intelligence of Sherlock Holmes?

Would you rather spend one night in the Overlook Hotel or Bates Motel?

Would you rather live in Gotham City or Metropolis?

Would you rather be transported into a period drama or a fantasy epic?

Would you rather know which fictional character inspired every famous author or which real person inspired every famous fictional character?

Would you rather watch your favorite movie with its original cast or its cast 30 years later?

Would you rather own a theater that only shows classic films or a bookstore that only sells classics?

Would you rather spend a day inside a Disney animated movie or a Pixar movie?

Would you rather have a cameo in every movie or a speaking role in one Oscar-winning film?

Would you rather erase one terrible movie from history or guarantee that one unfinished classic gets completed?

Food and Everyday Life Would You Rather Questions

Would you rather never eat dessert again or never eat cheese again?

Would you rather have unlimited coffee but no tea or unlimited tea but no coffee?

Would you rather eat the same breakfast every day or the same dinner every day?

Would you rather never cook again or never eat at a restaurant again?

Would you rather have a personal chef or a personal housekeeper?

Would you rather be able to eat anything without gaining weight or have all food be free?

Would you rather give up chocolate or cheese?

Would you rather give up salt or sugar?

Would you rather have enhanced taste or enhanced smell?

Would you rather always eat leftovers from a gourmet restaurant or fresh simple food?

Would you rather have free groceries for life or free restaurant meals for life?

Would you rather give up bread or pasta?

Would you rather eat breakfast food for every meal or dinner food for every meal?

Would you rather never have to grocery shop again or never have to do laundry again?

Would you rather have a refrigerator that never runs out of fresh, delicious food or a closet that never runs out of designer clothes?

Would you rather eat your favorite food at every meal for a year or never eat it again?

Would you rather be able to perfectly recreate any restaurant dish or any bakery item?

Would you rather have unlimited ice cream or unlimited popcorn?

Would you rather give up salt or sugar?

Would you rather eat only foods from your childhood or only foods you've never tried?

Would you rather not be able to taste food or not be able to feel emotions?

Would you rather have a kitchen that cleans itself or a bathroom and bedroom that clean themselves?

Would you rather never wash dishes again or never clean a toilet again?

Would you rather have to have every meal delivered forever or grow all your own food forever?

Would you rather always be able to cook delicious food that only you can eat or always be able to cook amazing food that everyone else can eat except you?

Would you rather eat at a different restaurant every day for a year or be able to cook delicious meals at home every day for a year?

Would you rather have unlimited fresh-baked bread or unlimited fresh-picked fruit?

Would you rather never drink juice again or never drink alcohol again?

Would you rather give up coffee or a good night's sleep?

Would you rather always have your favorite snack available or always have your favorite drink available?

Would you rather give up fried food or baked goods?

Would you rather be able to identify every ingredient in the foods you eat or every plant you see?

Would you rather eat only food you've made yourself or only food prepared by other people?

Would you rather have one enormous kitchen or one enormous bedroom?

Would you rather never have to clean the inside of your home or never have to maintain the outside of it?

Would you rather have every meal perfectly portioned or perfectly timed?

Would you rather eat the world's best meal once a year or a very good meal every day?

Would you rather have a pantry that restocks itself or a freezer that restocks itself?

Would you rather never be allowed to brush your teeth or never be allowed to shower?

Would you rather have clothes that never need washing or shoes that never wear out?

Would you rather always have the perfect temperature indoors or perfect weather outdoors?

Would you rather never lose your keys or never lose your phone?

Would you rather have a large house with tons of space but no windows or a tiny house with plenty of natural light?

Would you rather always have an empty dishwasher or an empty laundry basket?

Would you rather never wait in line again or never sit in traffic again?

Would you rather have every appliance controlled by your voice or your thoughts?

Would you rather always get the best parking space or never have to pay for parking?

Would you rather live without air conditioning or without heating?

Would you rather have a perfectly organized home or perfectly organized digital life?

Would you rather never have to make your bed again or never have to fold clothes again?

Truly Difficult Would You Rather Questions

Would you rather know when you will die or how you will die?

Would you rather be universally famous but misunderstood or completely unknown but deeply respected by everyone who knows you?

Would you rather have unlimited money but no free time or unlimited free time but only enough money to get by?

Would you rather relive your happiest day or erase your saddest day?

Would you rather be able to change one decision from your past or see the consequences of one decision you haven't made yet?

Would you rather have perfect health but live an ordinary life or extraordinary achievements with constant health setbacks?

Would you rather be remembered for one great thing or many small things?

Would you rather know every secret about your family or every secret about your closest friends?

Would you rather always know when someone is lying or always know what they really think?

Would you rather have the ability to forgive anyone instantly or never be hurt by anyone's actions?

Would you rather have one lifelong best friend or a hundred close friends who come and go?

Would you rather never experience embarrassment again or never experience regret again?

Would you rather be admired by everyone, or truly loved by a few people?

Would you rather have a guaranteed happy life where you never leave your hometown, or the freedom to take enormous risks and the ability to travel anywhere?

Would you rather be able to revisit any memory or create one perfect new memory every year?

Would you rather know what people say about you when you're not around or never know what anyone thinks of you?

Would you rather have your biggest mistake publicly known or your biggest secret privately discovered?

Would you rather always get what you want or always want what you have?

Would you rather have unlimited confidence or unlimited patience?

Would you rather have limitless wealth or be able to solve every major problem affecting humanity in your lifetime?

Would you rather live 200 years with an ordinary life or 80 years with an extraordinary one?

Would you rather have little money but plenty of free time or lots of money but no free time?

Would you rather be able to apologize perfectly or forgive perfectly?

Would you rather have your childhood home preserved forever or your favorite place as an adult preserved forever?

Would you rather know your greatest accomplishment in advance or your greatest failure in advance?

Would you rather have one chance to change the world or one chance to change your own life completely?

Would you rather be remembered accurately or remembered fondly but incorrectly?

Would you rather have everyone understand you or never have to explain yourself?

Would you rather be able to remove one fear from yourself or one fear from everyone?

Would you rather always be 10 minutes early or always have exactly the right amount of time?

Would you rather be extraordinarily talented at something you dislike or moderately talented at something you love?

Would you rather have to adopt an entirely new identity and leave everyone you know behind, or hit rock bottom in your own life and start over while keeping your own identity?

Would you rather know the truth about every conspiracy theory or every historical mystery?

Would you rather have unlimited knowledge or unlimited wisdom?

Would you rather always make the logical decision or always make the decision that makes you happiest?

Would you rather be able to change your appearance at will or your personality at will?

Would you rather never feel physical pain or never feel emotional pain?

Would you rather have everyone you meet remember you forever or be able to forget anyone instantly?

Would you rather have one conversation with your future self or one conversation with your past self?

Would you rather know exactly what your life would be like if you'd made a different career choice or a different relationship choice?

Would you rather have unlimited creativity or unlimited discipline?

Would you rather be able to know your own future and be unable to change it, or go on without knowing but still believing you can change it?

Would you rather always be around people who make great conversation, or always be able to make great conversation yourself?

Would you rather know the true meaning of life or know whether there is life elsewhere in the universe?

Would you rather be married to the love of your life who doesn’t love you, or be married to someone you don’t love but who loves you with all their heart?

Would you rather live in a world where nobody could lie or a world where nobody could keep secrets?

Would you rather have one hour with every person you've ever loved or one hour with every person you'll ever love?

Would you rather be given $10 million today or be given $1 million every year for the rest of your life?

Would you rather live your life believing there is a God only to die and realize there isn’t one, or live your life believing there’s no God, and discover that there is one after you die?

Would you rather know why you exist or know what happens after you die?