300 of the Best Would You Rather Questions Your Family Can Enjoy During the Holidays

Hanging out with friends is always a great time, but at some point, the party can start to lull.

A game of “Would You Rather” is a fun and spicy way to jazz up your next get-together and have a great time with your friends. Plus, it’s also fun to get to know them more. 

Another cool thing about this game is that “Would You Rather” questions don’t need to be formal or professional. Just think of questions about literally anything and shoot them to your friends! 

But, if the cat’s got your tongue and you find yourself struggling to come up with questions for your upcoming gathering, we’ve got you.

The Best Would You Rather Questions

Here are 300 fun, quirky, and unique “Would You Rather” questions to help you uncover a new side of your besties. 

Deep Would You Rather Questions

  1. Would you rather have to say every thought in your head or not be able to speak?
  2. Would you rather meet yourself in the past or see yourself in the future?
  3. Would you rather die young today with lots of friends or die old but with no loved ones?
  4. Would you rather not be able to laugh or not be able to cry?
  5. Would you rather remember everything in your life in great detail or never be able to remember anything?
  6. Would you rather live a day as someone else and remember everything or live a day as yourself but have no memory of what you did?
  7. Would you rather be unable to say thank you or be unable to ask for help?
  8. Would you rather be the richest person in the world but die tomorrow or live for 100 years in poverty?
  9. Would you rather know a hurtful truth or a peaceful lie?
  10. Would you rather go childless or without a life partner?
  11. Would you rather your worst enemy finds out your biggest fear or your most cherished loved one finds out your worst secret?
  12. Would you rather die a painful death at an old age or a peaceful death at a young age?
  13. Would you rather know how you’ll die or know when you’ll die?
  14. Would you rather sell one of your organs or sell your most treasured possession?
  15. Would you rather never get angry or never get jealous?
  16. Would you rather be wrongly convicted or get away with a crime that haunts you for the rest of your life?
  17. Would you rather have no government or have a government that’s corrupt?
  18. Would you rather live in a world where there are no laws at all or live in a world that’s crime-free but with lots of strict laws?
  19. Would you rather be a normal citizen in a utopia or a ruler in a dystopia?
  20. Would you rather have more money or have more time?
  21. Would you rather always be late or always be early?
  22. Would you rather live forever or die in ten years?
  23. Would you rather believe everything you’re told or be forced to always tell the truth?
  24. Would you rather get caught in a lie or hurt someone with the truth?
  25. Would you rather be always busy with no free time or be always bored with nothing to do?
  26. Would you rather live in a virtual reality but have free will or live in the real world when all your actions are controlled by someone else?
  27. Would you rather become famous when you die but be unknown during your lifetime or become famous during your lifetime but forgotten when you die?
  28. Would you rather be reincarnated with none of your memories or have all the knowledge in the world but only live once?
  29. Would you rather no who committed a crime but never be able to tell anyone or have to spend your whole life trying to hunt down a criminal and never knowing the answer?
would you rather questions
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Weather-Related Would You Rather Questions

  1. Would you rather sleep in a treehouse in a windstorm or sleep in a boat thunderstorm?
  2. Would you rather be caught in a typhoon or a massive earthquake?
  3. Would you rather it snow every day or it was always 100ºF and sunny?
  4. Would you rather live somewhere where it never rains or where it’s always raining?
  5. Would you rather be too hot or too cold?
  6. Would you rather wear boots in the summer or sandals in the winter?
  7. Would you rather have no air conditioning in the summer or no central heating in the winter?

Supernatural Would You Rather Questions

  1. Would you rather have the superpower of being invisible or reading minds?
  2. Would you rather freeze time or be the fastest person in the world?
  3. Would you rather read people’s minds or speak to animals?
  4. Would you rather be able to turn back time or freeze time?
  5. Would you rather be able to change the past or see the future?
  6. Would you rather know how the world will end or know how the world was created?
  7. Would you rather become a zombie or give birth to a zombie?
  8. Would you rather be Wendy or Tinkerbelle in Peter Pan?
  9. Would you rather your prince charming kisses you or not eat the poisoned apple from Snow White?
  10. Would you rather be a ghost that everyone remembers or a neglected human?
  11. Would you rather be able to breathe underwater or be able to fly?
  12. Would you rather be a giant or the size of Thumbelina?
  13. Would you rather go back in time 300 years or go 300 years into the future?
  14. Would you rather have people think poorly of you but secretly be a superhero or have people think highly of you but secretly be a criminal?
  15. Would you rather fall in love with a centaur or a mermaid?
  16. Would you rather go to Hogwarts or go to Narnia?
  17. Would you rather be able to teleport or be able to use telekinesis?

Wellness Would You Rather Questions

  1. Would you rather go deaf or go blind?
  2. Would you rather have the flu or the stomach bug?
  3. Would you rather go on a diet or workout to lose weight?
  4. Would you rather have a never-ending spring but always deal with allergies or a never-ending winter but never get sick?
  5. Would you rather burn your tongue or bite your lip?
  6. Would you rather forget how to talk or forget how to walk?
  7. Would you rather be immune to emotional pain or be immune to physical pain?
  8. Would you rather be stuck in a coma for a year or be stuck in jail for a year?
  9. Would you rather be double your weight or half your height?
  10. Would you rather work out at the gym or outdoors?
  11. Would you rather have a mild cat allergy or a deathly peanut allergy?
  12. Would you rather catch a cold once a month or get sick for a week once a year?
  13. Would you rather sneeze every minute for 24 hours or have a case of the hiccups for 24 hours?
  14. Would you rather get liposuction or laser hair removal?
would you rather questions
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Beauty-Related Would You Rather Questions

  1. Would you rather have the best dress without makeup or the worst dress with full makeup on?
  2. Would you rather only be able to shop at vintage stores or only be able to shop at designer stores?
  3. Would you rather be your ideal height or your ideal weight?
  4. Would you rather be extremely smart but ugly or be extremely beautiful but dumb?
  5. Would you rather be forced to do everything in a tracksuit or be forced to do everything in designer clothing?
  6. Would you rather have hair that never stops growing or be perpetually bald?
  7. Would you rather have to walk around barefoot for a day or wear wet tennis shoes for a day?
  8. Would you rather go a year without wearing makeup or a year wearing only pajamas?
  9. Would you rather have a big nose or crooked teeth?
  10. Would you rather have every shirt you try on be slightly too big or slightly too small?
  11. Would you rather be a tall person who is forced to wear high heels or a short person who can never wear high heels?

Friends and Family Would You Rather Questions

  1. Would you rather have no kids or have quadruplets?
  2. Would you rather be stuck at age 21 forever or live until 1000?
  3. Would you rather have your first child at 18 or your first child at 40?
  4. Would you rather be everyone’s best friend or be your parents’ favorite child?
  5. Would you rather your friends see your text messages or photos on your phone?
  6. Would you rather be invisible at your best friend’s wedding or not be invited to the wedding in the first place?
  7. Would you rather be the reason your team lost the Olympics or the reason your best friend lost their job?
  8. Would you rather be an only child or have 12 siblings?
  9. Would you rather have a lot of friends that you’re not very close with or only one friend who knows you extremely well?
  10. Would you rather be exiled for ten years or be shamed by everyone you know for ten years as a free person?
  11. Would you rather meet your great-great grandchildren or your great-great-grandparents?
  12. Would you rather have someone find everything you’ve ever posted online or have someone read your diary?
  13. Would you rather be the best friend of a famous person or be a famous person that nobody recognizes?
  14. Would you rather be late for your wedding or your best friend’s funeral?
  15. Would you rather save your best friend’s life but sacrifice five strangers’ lives or sacrifice your best friend’s life but save five strangers’ lives?
  16. Would you rather be funnier than all your friends or prettier than all your friends?
  17. Would you rather always speak your mind but come across as mean or never speak your mind but have everybody like you?
  18. Would you rather have no one attend your funeral or have no one attend your wedding?
  19. Would you rather move in with your parents or move in with someone who parties all the time?
  20. Would you rather take many selfies or only photos of your friends and family?
  21. Would you rather be a stay-at-home parent but poor or have both parents work but be rich?
  22. Would you rather have someone pay you to give them a ride to work or have someone fill your car with gas every time you drive them to work?

Financial Would You Rather Questions

  1. Would you rather lose all the photos you’ve ever taken or lose all your money?
  2. Would you rather be debt-free but only earn $1000 a month or have a debt of $100,000?
  3. Would you rather win the lottery and get all your earnings today or receive a monthly paycheck of $1000 for the rest of your life?
  4. Would you rather be rich or incredibly popular?
  5. Would you rather be rich because of a side hustle or be rich because of a trust fund?
  6. Would you rather only be able to take the bus for $2 everywhere you went or be forced to take a taxi but pay higher prices every time you went somewhere?
  7. Would you rather have people know personal details about your finances or have people know personal details about your relationship?
  8. Would you rather be poor but be able to give every homeless person in the world $1000 or be rich but not be able to share your money?

Holiday-Related Would You Rather Questions

  1. Would you rather get deodorant or a scale as a Christmas present?
  2. Would you rather go to Thanksgiving at your most annoying relative’s house or invite them to your house for Thanksgiving?
  3. Would you rather give a gift or receive a gift?
  4. Would you rather have a surprise party or plan your next party’s details?
  5. Would you rather never be able to trick-or-treat again or never receive a stocking on Christmas day?
  6. Would you rather celebrate Christmas in the summer or celebrate Thanksgiving in the spring?
  7. Would you rather never celebrate your birthday or never celebrate the holidays again?
  8. Would you rather celebrate your birthday alone or never have a birthday at all?
  9. Would you rather have an intimate luxury dinner party or a gigantic casual BBQ?

Career-Related Would You Rather Questions

  1. Would you rather be a garbage collector or a mortician?
  2. Would you rather work 12-hour days in front of a computer or 5-hour days doing hard manual labor?
  3. Would you rather clog the toilet on your first day at work or a first date?
  4. Would you rather be a tightrope walker or a trapeze artist?
  5. Would you rather have your camera on for every video call or have a microphone that never works in a video call?
  6. Would you rather be the only one drunk at the company party or be the only one sober at your bachelor party?
  7. Would you rather be able to live tax-free or get a month of paid time off each year?
  8. Would you rather have your dream job but never get a promotion or have a mediocre job where you’ll eventually become the boss?
  9. Would you rather have to work until the day you die at your dream job or only have to work ten years at a job you hate?
  10. Would you rather have a job with retirement and health benefits where you have to work in the office or a job with no benefits that lets you work from anywhere in the world?
  11. Would you rather have a boring job that pays well or an exciting job that pays poorly?
  12. Would you rather have a four-day workweek or leave work two hours early every day?
  13. Would you rather have a horrible boss but amazing coworkers or an amazing boss but horrible coworkers?
  14. Would you rather have someone steal your work and take credit for it or have your work published anonymously?
  15. Would you rather have to repeat a year of school or have to sit through a three-hour meeting every day for a year?
would you rather questions
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Romance Would You Rather Questions

  1. Would you rather wear a wedding dress to a funeral or wear funeral attire to a wedding?
  2. Would you rather spend an hour a day with your partner or only see each other on the weekend?
  3. Would you rather meet your partner in person or online?
  4. Would you rather your partner burped all the time or snored when they slept?
  5. Would you rather move abroad to be with the love of your life but never learn their language or be forced to have a long-distance relationship for the rest of your life?
  6. Would you rather throw up or have diarrhea on a first date?
  7. Would you rather go to a wedding alone or with someone you just met?
  8. Would you rather go on a date with a famous musician or go on a date with a famous athlete?
  9. Would you rather have someone wear a wedding dress to your wedding or have someone spill red wine on your wedding dress?
  10. Would you rather marry someone boring or marry someone overbearing?
  11. Would you rather find out your partner is having an affair or have to confess to having an affair?
  12. Would you rather go on a date with the hottest person you know or do an outstanding job at an interview for your dream job?
  13. Would you rather have an overly clingy partner or a partner that’s never available?
  14. Would you rather be stuck in an elevator with your partner’s ex or with your partner’s mom?
  15. Would you rather only be kissed or only be hugged?
  16. Would you rather travel the world with your lover for a year or spend a year stuck on a desert island with a celebrity?
  17. Would you rather throw up during your wedding or a business presentation?
  18. Would you rather be single forever or have an arranged marriage?
  19. Would you rather date someone ten years older than you or ten years younger?
  20. Would you rather have a partner who’s a genius or an incredibly handsome partner?
  21. Would you rather have all your partner’s exes show up to your wedding or have all your exes show up to your wedding?
  22. Would you rather break up with someone or have someone break up with you?
  23. Would you rather your partner die first or you die first?
  24. Would you rather go on a bad date with someone but have to see them every day for the rest of your life or have an amazing kiss with someone but never see them again?
  25. Would you rather have a complete meal that’s just mediocre or one tiny bite of the most delicious food in the world?
  26. Would you rather be loved by someone you don’t love or love someone who doesn’t love you back?
  27. Would you rather spend a day with your ex or your worst enemy?
  28. Would you rather get rejected by everyone you fall in love with or never fall in love again?
  29. Would you rather fall in love in jail but have your partner be the best person in the world or fall in love online with someone who’s secretly evil?
  30. Would you rather elope or have a huge wedding?
  31. Would you rather get a cheap engagement ring that looks gorgeous or an expensive engagement ring that’s hideous?
  32. Would you rather honeymoon on the beach but it rains all the time or honeymoon on a snowy mountain, but it’s sunny all the time?
  33. Would you rather get catfished or get scammed out of $1000?
  34. Would you rather get your heart broken or lose your best friend?
  35. Would you rather get married to the love of your life but not have any friends or family members attend or get married to someone you don’t love but have all the people you love at the wedding?

Food Would You Rather Questions

  1. Would you rather eat turtle soup or escargot?
  2. Would you rather see only in black and white or never be able to taste again?
  3. Would you rather get ridiculously drunk after just one drink or never get drunk, no matter how much you drink?
  4. Would you rather eat live sea urchins or eat dead slugs?
  5. Would you rather give up alcohol forever or give up soft drinks forever?
  6. Would you rather ask someone to buy you a meal or go dumpster diving for your food?
  7. Would you rather eat PB&J sandwiches with no jelly or pizza with no sauce?
  8. Would you rather eat a stranger’s leftovers at a restaurant or eat mystery leftovers from your fridge?
  9. Would you rather eat only ramen or only canned soup for a week?
  10. Would you rather eat out every night or cook at home every night?
  11. Would you rather eat only hamburgers for the rest of your life or eat only hot dogs?
  12. Would you rather eat French fries or potato chips?
  13. Would you rather only be able to eat salad or only be able to eat soup?
  14. Would you rather eat at your favorite restaurant or have your favorite home-cooked meal?
  15. Would you rather only be able to drink coffee or never be able to drink coffee again?
  16. Would you rather eat soup in the summer or ice cream in the winter?
  17. Would you rather eat at a brand new restaurant or eat at your favorite restaurant?
  18. Would you rather be tired all the time, no matter how much you sleep, or be hungry all the time, no matter how much you eat?
  19. Would you rather have all your food be bland or have all your food be too salty?
  20. Would you rather be forced to eat your least favorite food or be forced to stay awake for 24 hours?
  21. Would you rather eat a stale cookie or drink flat soda?
  22. Would you rather drink only coffee or tea?
  23. Would you rather drink Starbucks or Dunkin’ Donuts?
  24. Would you rather only be able to eat McDonald’s or only be able to eat Burger King?
  25. Would you rather only eat ketchup or only eat mustard?
  26. Would you rather give up eating savories or sweets?
  27. Would you rather eat breakfast for dinner or dinner for breakfast?
  28. Would you rather eat alone in a restaurant or eat in a crowded room at home?
  29. Would you rather eat only vegetables or only fruit for the rest of the day?
  30. Would you rather get a free shopping spree or a free all-you-can-eat gourmet meal?
  31. Would you rather eat your favorite dessert or drink your favorite coffee?
  32. Would you rather eat a slice of pizza with peanut butter on top or a hamburger with vegemite inside?
  33. Would you rather eat spoiled milk or your booger?
  34. Would you rather have to live without bacon or live without chocolate?
  35. Would you rather eat a maple bacon donut or a slice of Hawaiian pizza?
  36. Would you rather have a food fight or a pillow fight?
  37. Would you rather have your Starbucks order messed up or your Amazon order messed up?
  38. Would you rather only be able to order off the kid’s menu or only be able to order the most expensive food on the menu?
would you rather questions
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Entertainment Would You Rather Questions

  1. Would you rather be able to play every instrument in the world or be able to speak every language?
  2. Would you rather live without movies and TV shows or live without music?
  3. Would you rather take part in The Bachelor or take part in Wipeout?
  4. Would you rather be forced to watch your least favorite movie once or be forced to watch your favorite movie three times in a row? 
  5. Would you rather go to the ballet or go to see the orchestra?
  6. Would you rather be a movie star or a Broadway star?
  7. Would you rather go all day without Netflix or Youtube?
  8. Would you rather perform on stage with Rihanna or party with Katy Perry?
  9. Would you rather be a world-renowned comedian but never find anything funny, or find everyone’s jokes funny but never be able to tell a good joke of your own?
  10. Would you rather spend a day reading your favorite book or watching your favorite TV show?
  11. Would you rather have a soundtrack play in real life or never hear music again?
  12. Would you rather get front-row seats to a concert for a band you don’t know or get back-row seats to your favorite band’s show?
  13. Would you rather hear your favorite artist perform live or meet your favorite book author?
  14. Would you rather sneak into a movie theater without paying or sneak out of a restaurant without paying?
  15. Would you rather have a movie made about you or write an autobiography?
  16. Would you rather go to the movies alone or a fancy restaurant alone?
  17. Would you rather only be able to listen to the same song for the rest of your life or never be able to listen to the same song twice for the rest of your life?

Funny Would You Rather Questions

  1. Would you rather have extra-long fingernails or hair down to your ankles?
  2. Would you rather have a very deep voice or a very high-pitched voice?
  3. Would you rather be unable to shave your armpits or unable to shave your legs?
  4. Would you rather have only four fingers or have a tail?
  5. Would you rather empty a swimming pool with a bucket or swim in swimming pool full of jellyfish?
  6. Would you rather have a giant tattoo on your forehead or have no teeth?
  7. Would you rather have no dishwasher or no microwave?
  8. Would you rather get stuck at the top of a roller coaster or not get to ride anything at the theme park that day?
  9. Would you rather do a color run or a bubble run?
  10. Would you rather play a single game of Monopoly or a 3-hour game of Uno?
  11. Would you rather sing instead of speak or run instead of walk?
  12. Would you rather have no running water in the house or no electricity?
  13. Would you rather never be able to shower again or never be able to wash your clothes again?
  14. Would you rather wear used underwear or used socks?
  15. Would you rather get stuck on an elevator or a ski lift?
  16. Would you rather reuse your underwear or use your friend’s toothbrush?
  17. Would you rather accidentally send a naughty message to your teacher or parents?
  18. Would you rather go a day without a shower or without brushing your teeth?
  19. Would you rather live a day without the internet or a day without your pet?
  20. Would you rather have bad breath or bad body odor?
  21. Would you rather have an elephant’s nose or a giraffe’s neck?
  22. Would you rather wear stripes or polka dots for a week?
  23. Would you rather lose your phone or your laptop?
  24. Would you rather go to jail for one year or live in a haunted house for one year?
  25. Would you rather live without drinking straws or without paper towels?
  26. Would you rather eliminate paper or plastic?
  27. Would you rather have no sleep for one whole day or no phone?
  28. Would you rather touch a snake or a crocodile?
  29. Would you rather get stuck on a lengthy phone call or get stuck in traffic?
  30. Would you rather have a fancy car that only takes diesel or a lousy car that you can fill for $10 per tank?
  31. Would you rather have no legs or no hands?
  32. Would you rather deal with a termite infestation in your walls or a colony of bats living in your attic?
  33. Would you rather have three eyes or three ears?
  34. Would you rather live next to a neighbor who plays the drums late at night or a cranky old man who yells every time you leave your house?
  35. Would you rather have a sinkhole in your backyard or live on a street that’s full of potholes?
  36. Would you rather receive a broken record player or a used designer dress?
  37. Would you rather only be able to use single-ply toilet paper or have to use hand dryers instead of paper towels?
  38. Would you rather do a float tank for a day or go to a sensory overload room for a day?
  39. Would you rather have everyone recognize you but call you the wrong name or have no one recognize you but always get your name right?
  40. Would you rather be okay at everything you try or excellent at just one skill?
  41. Would you rather hit every red light when you leave the house or only have ‘E-service on your phone?
  42. Would you rather never be able to use your phone or never be able to use the computer?
  43. Would you rather have a fast bike or a super slow car?
  44. Would you rather have a photographic memory or an incredible imagination?
  45. Would you rather be a math wizard or an artistic genius?
  46. Would you rather get a tattoo or get a body piercing?
  47. Would you rather go for a walk with a cheetah or go for a walk with a turtle?
  48. Would you rather go without soap or go without toothpaste for the rest of your life?
  49. Would you rather have a butler or a maid?
  50. Would you rather have to repeat high school or have to repeat college?
  51. Would you rather only be able to talk on the phone or only be able to text?
  52. Would you rather spend a night at a party or at home reading a book?
  53. Would you rather never dance again or never sing again?
  54. Would you rather live next to the airport or live next to the sports stadium?
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Adventurous Would You Rather Questions

  1. Would you rather go on an all-expenses paid vacation for a year or get an all-expenses paid shopping spree?
  2. Would you rather have to run a marathon or swim a 100-meter dash?
  3. Would you rather go rock climbing without a harness or drive a go-kart without breaks?
  4. Would you rather spend your vacation in a cool city or the wilderness?
  5. Would you rather only be able to go on vacation to the same place each year or never be able to take another vacation?
  6. Would you rather get trapped in Bora Bora for a week or in Paris for a week?
  7. Would you rather have to wear snowshoes every time you leave the house or have to walk on stilts?
  8. Would you rather go rock climbing or cliff jumping without safety equipment?
  9. Would you rather visit the pyramids or visit the Amazon river?
  10. Would you rather live in a tiny home in the most beautiful place in the world or live in a gorgeous mansion in the middle of nowhere?
  11. Would you rather take a one-way trip to Mars or never be able to travel abroad again?
  12. Would you rather get lost in the safest city in the world or know the map of the city by heart but be in the most dangerous city in the world?
  13. Would you rather speak every language fluently but be unable to travel or be able to travel wherever you want but never be able to learn a foreign language?
  14. Would you rather go scuba diving or sky diving?
  15. Would you rather live in a houseboat or live in a van?
  16. Would you rather go skiing or snowboarding?
  17. Would you rather use an old-school map or a compass if you were lost at sea with no GPS?
  18. Would you rather go skydiving or bungee jumping?
  19. Would you rather go to your dream destination or meet your favorite actor?
  20. Would you rather swim with sharks or stingrays?
  21. Would you rather have your driver’s license taken away or your passport taken away?
  22. Would you rather sail the world for a whole year or travel via airplane for a whole year?
  23. Would you rather get stuck on a deserted island or on the top of a mountain?
  24. Would you rather go camping in a tent in the desert or get snowed in at a cabin in the mountains?

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