Absolute Hardest Would You Rather Questions (250+ Fun Ones)

Looking for the hardest would you rather questions to ask? Playing the ‘would you rather’ game can be good fun. Apart from having a good time, the answers to these questions tell you a lot about a person. This question calls for thinking and answering in a logical way. The questions present two choices and tests the decision-making ability of a person.

You can play this game as a team building activity or just for fun with friends. To make the game more interesting, we have curated the hardest questions in this category. Answering these questions is not easy and calls for a lot of thinking. You will have a great time completing this exercise, as would the person answering the questions.

Hardest would you rather questions

Would you rather prefer to be taller than how much you are now or weigh less than how much you do now?
Would you rather like to live in a house with animals or would you like to live in a barn with animals in it?
Would you rather live in a country with a low cost of living and bad weather, or a country with amazing weather?
Would you rather be sweet and dumb, or smart but a jerk?
Would you rather prefer to be trapped in the Lord of the Rings Universe or in the Matrix world?
Would you rather prefer to spend time watching a movie or reading the book on which it was based?
Would you rather be known as a very intelligent person, or as someone who is always joyful and hilarious?
Would you rather go back in time and meet your ancestors or would you want to go to the future to meet your descendants?
Would you rather make just enough money needed to survive or would you want to be rich beyond by dreams by doing things that your family dislikes?
Would you rather eat the same food daily or prefer to give up social media forever?
Would you rather prefer to meet a famous person who doesn’t talk much or a normal person who is funny and entertaining?
Would you rather meet your favorite singer/musician or your all-time favorite author?
Would you rather get a chance to be the Mayor or your city for a year or the President of the US for a day?
Would you rather want a colleague to fall in love with you or your boss to fall in love with you?
Would you rather want to know how long you are going to live or how you would die?
Would you rather never brush or comb your hair again or prefer to never brush your teeth again?
Would you rather go for a show that you don’t like because your family members want to or take them to a show of your choice?
Would you rather prefer to go on a vacation once a year or go on a holiday for 1 day for every month of the year?
Would you rather prefer to search in a dumpster for food or stand outside a restaurant and ask people to buy you food?
Would you rather prefer to live in a big city in a small home or in a rural area in a huge home?
Would you rather want to read your mother’s personal diary, or would you be willing to have your mother read your personal diary?
Would you rather prefer to have a small birthday party inviting very close friends, or would you like to have a big bash inviting a large number of people?

Hardest would you rather questions for couples

Would you rather want to outlive your partner or want that your partner should live longer than you?
Would you rather want to have a great career and earn money with less time or family, or prefer to spend more time with family with lesser earnings?
Would you rather have a partner who is extremely good looking but has a disagreeable personality? Or a partner with the most pleasant personality and is plain looking?
Would you rather be trapped in a horror movie situation with your best friends or in a rom-com with your worst enemies?
Would you rather prefer to be forgotten after 50 years or be still remembered as someone who was infamous?
Would you rather want to date someone who is very punctual or someone who never forgets anything?
Would you rather want to have the power to stop time whenever you want or want to have the power to become invisible?
Would you rather prefer to travel a lot or meet many people during your regular work routine?
Would you rather want to be 80 years and live forever, or want to be 10 years and live forever?
Would you rather have just two great friends or prefer having a hundred average friends?
Would you rather prefer having two kids or having no kids at all?
Would you rather achieve all your personal goals or prefer to achieve all your professional goals?
Would you rather want the govt. to abolish capitalism or would you want to become a millionaire yourself?
Would you rather want to spend one intimate hour with your partner every day or spend one full day every month?
Would you rather have all the money you want or all the time you want?
Would you rather have a partner who earns more than you or someone who earns less than you?
Would you rather your partner works with you in the same company as you do or works somewhere else?
Would you rather prefer that your partner is a homemaker taking care of the family or would you want your partner to focus on career?
Would you rather want to eat out once a week or eat out every day for one meal?
Would you rather want to watch a movie with your partner or go out for a day trip?
Would you rather prefer that your partner be expressive with their emotions or want them not to be too much expressive?
Would you rather have a partner whose political views are the same as yours or wouldn’t mind if your partner’s political views are diametrically opposite?
Would you rather want your partner to have a job where they travel for 3 days every month or want them at a job not involving travel?
Would you rather prefer your partner to get angry and scream at you for 5 minutes, or prefer your partner to stop talking for a day when they are angry?

Hardest would you rather questions

Would you rather get a new puppy for your birthday or get an increase in your pocket money every month?
Would you rather get the ability never to cry again, or would you like to be able to cry for 10 minutes at random daily?
Would you rather want to be a famous musician/rockstar or a famous actor?
Would you rather never be able to use a computer again, or would you choose never using your mobile phone again?
Would you rather play at home using your computer or mobile, or would you want to play outdoors with your friends?
Would you rather turn into the ugliest person in the world or would you rather be the worst smelling person in the world?
Would you rather get a chance to meet an Avenger or a DC superhero?
Would you rather be allowed to keep awake an hour extra each day watching TV or would you want to spend the entire Sunday in front of the TV?
Would you rather be an expert who is specialized in one area and a master, or would you prefer to good at many things?
Would you rather not eat junk food for 3 weeks a month, or would you prefer to be allowed to eat junk food for 2 days a month?
Would you rather do cleaning chores inside the home or would you want to do cleaning work outside the house?
Would you rather get the magical wand of Harry Potter or would you want the hammer of Thor with you?
Would you rather want to worry about being infected by germs or would you want to be scared by monsters under the bed?
Would you rather get the superpower of being able to fly or would you want the superpower of traveling to any place by teleporting?
Would you rather prefer to have teeth that doesn’t get spoiled or have a tummy that doesn’t pain no matter what you eat?
Would you rather spend your free time teaching what you to know to younger kids or would you want to spend time with the elderly in an old age home?
Would you rather get a chance to ride on a camel, or would you prefer an elephant ride?
Would you rather want to own an exotic spider as a pet or a python as a pet?
Would you rather eat cake or ice-cream?
Would you rather eat pizza or burger?
Would you rather eat all your food using a fork or a spoon for the entire week?
Would you rather be a math teacher when you grow up or a sports coach?
Would you rather be a surgeon who treats animals or a surgeon who treats humans?

Hardest would you rather questions for adults

Would you rather prefer to skydive or choose bungee jumping?
Would you rather marry someone you have known all your life or someone you have just met?
Would you rather prefer to be abducted by an alien or be taken hostage by crooks?
Would you rather prefer to eat food that is undercooked or food that is burnt and overcooked?
Would you rather prefer to make your own food for an entire month or eat food from outside for the full month?
Would you rather get a tattoo on your neck or have your tongue pierced?
Would you rather have your life story being turned into a book or do you want it to be made into a movie?
Would you rather make a speech in front of the town hall before thousands of people or want to be interviewed on live TV in a studio?
Would you rather stay in a room with a snake or be ready to stay in a room with a tarantula?
Would you rather prefer that everyone else in the world become taller than you or they become stronger than you?
Would you rather put your hand inside a hornet’s nest, or would you be willing to kick a sleeping grizzly?
Would you rather have 2 toes removed or prefer to have just one finger removed?
Would you rather prefer to travel a hundred years into the future or would you want to go back hundred years to the past?
Would you rather prefer to be in a tank during a war or in a submarine?
Would you rather prefer to forget your spouse’s birthday or would you be ready to do the dishes every day?
Would you rather eat food that is very good for health but awful to taste? Or food that tastes awesome but would not be good for your health?
Would you rather prefer to be the richest person on earth or the most intelligent person on earth?
Would you rather want the ability to be able to remember every single thing you have read or get the ability to remember everything you hear?
Would you rather prefer to have a photographic memory, or would you choose to have a vivid imagination?
Would you rather get a chance to work in a movie as the lead actor or would you want to be part of your favorite sports team?
Would you rather choose a job that pays less but allows you to work from home? Or would you choose a job that pays more where you have to go to work daily?
Would you rather prefer to live a life free of all risks and danger, or would you be willing to live a life where there are normal risks?
Would you rather live for only 10 more years in a mansion or for 30 more years on the street?

Hardest would you rather questions for coworkers

Would you rather come to office for all days of the week, or would you prefer to work from home coming to office only when needed?
Would you rather work at the same company for the rest of your life at the same salary, or would you be ready to take the risk of changing jobs every 5 years?
Would you rather work at a place that you dislike but earn a good salary or work at a great place with a meager salary?
Would you rather work at a company where you need to sit in front of the computer the whole day? Or would you be ready to do manual labor for at least 4 hours each day?
Would you rather never fail again in whatever you do or never be rejected ever again?
Would you rather work in a dream job that requires a commute for 2 hours or work in a place next to your home at a lower pay?
Would you rather prefer to get your own lunch to work daily or get free food from the company, but without having a choice or knowing what would be served?
Would you rather work in a job where you get a fixed salary every month or be ready to get paid the money you deserve based on your work output?
Would you rather work for a large company with thousands of employees or a small company with just a few people?
Would you rather be the CEO of your company ready to take maximum risks or prefer to be an ordinary executive with no tensions?
Would you rather work for an extra hour and get an hour break or work without breaks but be allowed to leave early?
Would you rather work on your own or be part of a team?
Would you rather work in a company with no formal organization structure, or would you work in a place where roles & responsibilities are clearly defined?
Would you rather work in an office that is always noisy or do you want to work in a quiet environment?
Would you rather listen to music using headphones while working or would you be fine is music plays on speakers?
Would you rather prefer to come late to work and leave late or come early and leave early?
Would you rather prefer working on projects that you are familiar with or work on new projects where you need to learn new skills?
Would you rather be an executive who does the work or a manager who delegates work to others and is overall responsible?
Would you rather retire at 65, or would you prefer to keep working as long as you are in good health?
Would you rather work as a full time employee earning regular pay or work as a freelancer earning based on the work you do?

Food would you rather questions (hardest)

Would you rather eat cooked foods or raw foods that are uncooked?
Would you rather eat at a highly rated restaurant that is expensive or a low-cost café that does not have any ratings?
Would you rather prefer to lose your sense of smell or your sense of taste?
Would you rather be allergic to eggs or be allergic to peanuts?
Would you rather eat using cutlery like spoons and forks or be willing to eat using your bare hands?
Would you rather eat as much salad as you want or eat a limited quantity of your favorite dish?
Would you rather never be allowed to eat bananas, or would you never eat apples?
Would you rather that you eat all food using chopsticks or eat it using a fork?
Would you rather live in a world with no vegetables or in a world with no pizza?
Would you rather prefer to give up coffee or give up eating meat?
Would you rather eat what you want without caring about the consequences or do you want to follow a strict diet?
Would you rather go on a date to a fancy restaurant or take the date to your favorite small eatery?
Would you rather be willing to give up potato chips forever or choose to give up popcorn forever?
Would you rather have ice-cream on a hot day or prefer to have fresh fruit juice?
Would you rather eat burger and fries or steak?
Would you rather drink hot coffee or cold coffee?
Would you rather eat a dish with excess of salt or one made with excess of sugar?
Would you rather go without food an entire day or be willing to eat stale food?
Would you rather not eat turkey for Thanksgiving or not eat candy for Halloween?
Would you rather cook a quick dish that is not so tasty or a delicious dish that takes a lot of time to cook?
Would you rather be willing to give up drinking sodas or give up having desserts?
Would you rather never eat chocolate cake again or choose not to ever eat fries?
Would you rather choose to eat only square-shaped food or circle-shaped food?
Would you rather eat only Italian food for an entire week or only Chinese food for the whole week?
Would you rather eat food prepared by your mom or food cooked in your favorite restaurant?
Would you rather chew an onion or raw garlic for 10 minutes?
Would you rather eat bread with jam every day or bread with peanut butter each day?
Would you rather be a vegetarian or an omnivore?
Would you rather prefer to drink only green tea as part of a diet or only eat boiled vegetables?
Would you rather eat every meal with mayo or with ketchup?

Funny would you rather questions (hardest)

Would you rather prefer to spend an entire day with a senator or with the head chef of a leading restaurant?
Would you rather be allergic to your favorite food or choose to be allergic to animals?
Would you rather have superpowers that you don’t know how to use or be a psychic whose predictions no one believes?
Would you rather lose the ability to run or not be able to swim again?
Would you rather fight a tiger or Thanos?
Would you rather want to turn into a dog or a cat for an hour every time you sneeze?
Would you rather want people to forget your name or mispronounce it every time?
Would you rather prefer to have a dragon as a pet you can’t properly control or a talking elephant?
Would you rather eat broccoli for the rest of your life or get up at 5 am every day?
Would you rather be willing to have poor eyesight or have difficulty in hearing?
Would you rather praise your boss every single day or prefer to slap yourself daily?
Would you rather want to have your right hand tied behind your back or have a tape on your mouth always?
Would you rather get your head fully shaved or get your lips pierced?
Would you rather prefer to tell lies to your friends or tell the truth to your enemies?
Would you rather have your head replaced by a toaster or have a cactus instead of your spine?
Would you rather never celebrate your birthday or have your family never celebrate any holiday?
Would you rather be a teacher at high school or a circus clown?
Would you rather have a dry mouth always or have a bad flatulence problem?
Would you rather prefer to speak in rhymes or speak in riddles?
Would you rather travel everywhere on a donkey or carry a monkey on your shoulders wherever you go?
Would you rather be as tall as King Kong or as small as a beetle?
Would you rather be reincarnated as a human again or as an animal?
Would you rather never use brush your teeth again or never have a bath?
Would you rather have your right hand replaced by a hook or have your right leg replaced by a peg?
Would you rather travel to the world of Harry Potter or the world of Lord of the Rings?
Would you rather be a goldfish living in a bowl or a rabbit living in a forest?

Weird would you rather questions (hardest)

Would you rather that a bird dies every time you laugh, or would you be willing to have a bird come out of your mouth every time you yawn?
Would you rather wrestle with a pig in mud or fight off a python trying to coil around you?
Would you rather wear the same dress for every single day of your life or do the same work for every single day of your life?
Would you rather be the smartest person in the room or the most effective person in the room?
Would you rather have to eat meat for every meal with no other carbs or fats. Or eat carbs for every meal?
Would you rather spend your whole life with a disability or live your entire life happy?
Would you rather wear wet socks to the gym or wet underwear?
Would you rather someone look at your Google search history or look through your bank account?
Would you rather marry your best friend or have your partner become your best friend?
Would you rather eat foods that were rotten or fermented?
Would rather all the music you listen to be a couple of tones higher or lower?
Would you rather die a painful death that was fast or a slow death that wasn’t fast?
Would you rather eat the same dinner every night or drink the same thing every night?
Would you rather drink sour milk or drink someone’s urine?
Would you rather not have your taste buds work or not be able to feel anything?
Would you rather have a million dollars for only one year or make a mediocre income for the rest of your life?
Would you rather all your money be locked away and safe or available to you but victim to robbery at times?
Would you rather fly in a plane with a damaged engine or travel in a boat with no engine?
Would you rather prefer to die in an accident or live until the age of 100 without being able to talk?
Would you rather wear sweatpants daily or wear a tuxedo on every day?
Would you rather be born without having knees or without having elbows?
Would you rather be able to predict the weather or detect when someone is lying?
Would you rather have smelly feet or would have bad breath?
Would you rather wear shoes that 2 sizes big or wear jeans that are 1 size smaller?
Would you rather prefer to get a tattoo done discretely where it is not visible or would you rather get a face tattoo done on someone dear to you in a visible region?
Would you rather allow people to see your internet browsing history or get to see all your text messages?
Would you rather want to communicate using only emojis or communicate using only single words?
Would you rather surrender your credit card and not use it again or give up the ability to use GPS permanently?
Would you rather hunt and forage in the wild for whatever you eat or would you get your food daily from McDonald’s?
Would you rather prefer to meet a celeb as soon as you get up in the morning or would you meet them well dressed but without deodorant?
Would you rather want to sing your all-time favorite song in a stadium in front of thousands of people or in front of the original singer?
Would you rather give up all the money you have or give up all the things and material possessions you own?
Would you rather drink using a sipper cup when you go to a bar or wear a bib while eating when you go to a restaurant?
Would you rather prefer to be abducted by the bad guys from the Wild West or from Blackbeard and his pirates?
Would you rather want to sniff someone you meet for the first time (just like a dog does) or eat dog food for lunch and dinner every day?
Would you rather go out in public with a large stain on your pant or with toilet paper stuck to your back?
Would you rather only eat food that begins with the letter C, or would you eat only food starting with the letter P?

Hardest would you rather questions (images to share)

More fun games to play

Download as PDF

Inside this article

Tags:

Questions

Fact checked:
Board reviewed by Marianne Tomlinson, LCSW (Couples and Family Therapy). Content is rigorously reviewed by a team of qualified and experienced fact checkers. Learn more.

About the author

Ryan Sanderson (LCSW) Ryan is a game and relationship enthusiast who enjoys all things quizzes, games, fun, love, relationships, and family. He's a licensed social worker and helps families, couples, and children in need. He's spoken about love and relationships on Salon.com, Forbes, and Mirror, to name a few.