131 Would-You-Rather Questions to Kickstart Your Team’s Next Social Event

| Employee Engagement, Team Building
131 Would You Rather Questions to Kickstart Your Teams Next Social Event featured image
If there’s a way of getting to know your colleagues that’s more fun than would-you-rather questions, we haven’t found it yet. So, we’ve compiled a comprehensive list of questions you can use to break the ice with your team. 

When it comes to getting your colleagues better, there are few ways more efficient (or hilarious) than with would-you-rather questions. 

If you’re unfamiliar with these questions, the premise is pretty straightforward: you ask somebody a question with an either-or outcome, and they have to decide which they’d prefer. 

But here’s where it gets good: would-you-rather questions offer virtually endless possibilities, from thought-provoking and insightful to downright ridiculous. 

And we’ve compiled a list of 131 would-you-rather questions that cover the entire spectrum.  

Entertainment Themed Would You Rather Questions  

a large sign with the word ask written on it for would you rather questions
  1. Would you rather work for Michael Scott or Mr. Burns? 
  1. Would you rather watch a TV show or watch YouTube? 
  1. Would you rather be on a survival reality show or dating show? 
  1. Would you rather go to the movie theaters or watch a movie from home? 
  1. Would you rather Danny DeVito or Danny Trejo play you in a movie? 
  1. Would you rather watch nothing but Hallmark Christmas movies or nothing but horror movies? 
  1. Would you rather go backstage with your favorite band or be an extra on your favorite TV show? 
  1. Would you rather sip gin with Ryan Reynolds or shoot tequila with Dwayne “The Rock” Johnson? 
  1. Would you rather watch nothing but The Office or Friends for the rest of your life? 

Weird and Wacky Would You Rather Questions 

a team of colleagues laughing at some weird and wacky would you rather questions
  1. Would you rather get your paycheck given to you in pennies or never be able to use cash again? 
  1. Would you rather spend the weekend with pirates or ninjas? 
  1. Would you rather smell with your hands or talk with your feet? 
  1. Would you rather be forced to sing along or dance to every single song you hear? 
  1. Would you rather swim in a pool full of Nutella or a pool full of maple syrup? 
  1. Would you rather buy 10 things you don’t need every time you go shopping or always forget the one thing that you need when you go to the store? 
  1. Would you rather never be able to go out during the day or never be able to go out at night? 
  1. Would you rather always have B.O. and not know it or always smell B.O. on everyone else? 
  1. Would you rather spend a week in the forest or a night in a real haunted house? 
  1. Would you rather be 11 feet tall or nine inches tall? 
  1. Would you rather have to wear every shirt inside out or every pair of pants backward? 
  1. Would you rather be always stuck in traffic but find a perfect parking spot or never hit traffic but always take forever to park? 
  1. Would you rather cuddle a koala or pal around with a panda? 
Would you rather be royalty 1000 years ago or an average person today would you rather question
  1. Would you rather be royalty 1,000 years ago or an average person today? 
  1. Would you rather have to wear sweatpants everywhere for the rest of your life or never wear sweatpants again? 
  1. Would you rather have a photographic memory or an IQ of 200? 
  1. Would you rather have skin that changes color based on your emotions or tattoos appear all over your body depicting what you did yesterday? 
  1. Would you rather have seven fingers on each hand or seven toes on each foot? 
  1. Would you rather have a tattoo of the title of the last book you read or the last TV show you watched? 
  1. Would you rather have a third ear or a third eye? 
  1. Would you rather live in a treehouse or in a cave? 
  1. Would you rather sell all of your possessions or sell one of your organs? 
  1. Would you rather hunt and butcher your own meat or never eat meat again? 
  1. Would you rather walk to work in heels or drive to work in reverse? 
  1. Would you rather be the absolute best at something that no one takes seriously or be average at something well respected? 
  1. Would you rather master every musical instrument or every type of sport? 
  1. Would you rather be punished for a crime you didn’t commit or have someone else take credit for one of your major accomplishments? 
  1. Would you rather eat the same thing for every meal for a year or be able to eat whatever you wanted, but only once every three days? 
  1. Would you rather always be 10 minutes late or always be 20 minutes early? 
  1. Would you rather win the lottery but have to spend it all in one day or triple your current salary forever? 
  1. Would you rather be in history books for something terrible or be forgotten completely after you die? 
  1. Would you rather be rich working a job you hate or poor working a job you love? 
  1. Would you rather be able to run at 100 miles per hour or fly at 10 miles per hour? 
  1. Would you rather have the ability to see 10 minutes into the future or 150 years into the future? 
  1. Would you rather live without heat and AC or live without social media? 
  1. Would you rather never get another present in your life but always pick the perfect present for everyone else or keep getting presents but giving terrible ones to everyone else? 
  1. Would you rather be the star player on a losing team or warm the bench on a championship roster? 
  1. Would you rather get trapped in the middle of a food fight or a water balloon fight? 
  1. Would you rather have super-sensitive taste buds or super-sensitive hearing? 
  1. Would you rather start a colony on another planet or be the leader of a country on Earth? 
  1. Would you rather be a genius everyone thinks is an idiot or an idiot everyone thinks is a genius? 
  1. Would you rather sneeze nonstop for 15 minutes once every day or sneeze once every three minutes of the day while you’re awake? 
  1. Would you rather live in a house haunted by friendly ghosts or be a ghost reliving your average day after you die? 
  1. Would you rather oversleep every day for a week or not get any sleep at all for four days? 
  1. Would you rather take a pill a day for nutrients and to feel full, but never eat anything again or eat whatever you want but never really feel full? 
Would you rather look strong and be weak or look weak and be strong would you rather question
  1. Would you rather look strong and be weak or look weak and be strong? 
  1. Would you rather go back to kindergarten with everything you know now or know now everything your future self will learn? 
  1. Would you rather eat only pizza for a year or not eat any pizza for five years? 
  1. Would you rather find true love today or win the lottery next year? 
  1. Would you rather be forced to live the same day over and over again for a full year, or take 3 years off the end of your life? 
  1. Would you rather always have wet socks or a small rock in your shoe? 
  1. Would you rather have one wish granted today or 10 wishes granted 20 years from now? 
  1. Would you rather run at 100 mph or fly at 20 mph? 

Travel Themed Would You Rather Questions 

a neon question mark for would you rather questions
  1. Would you rather travel to a beach destination or ski resort? 
  1. Would you rather travel to space or travel to the past? 
  1. Would you rather travel by train or travel by plane? 
  1. Would you rather travel the world for free for a year or have $50,000 to spend however you please? 
  1. Would you rather visit the International Space Station for a week or spend a week in a hotel at the bottom of the ocean? 

Personal Would You Rather Questions  

a man on his computer sharing his answers to personal would you rather questions
  1. Would you rather go deep-sea diving or bungee jumping? 
  1. Would you rather for your birthday, receive cash or gifts? 
  1. Would you rather go to a house party or a bar? 
  1. Would you rather be a kid your entire life or be an adult? 
  1. Would you rather get a hand-written card or a phone call? 
  1. Would you rather know the answer to every trivia question or the lyric to every song? 
  1. Would you rather go for a run or go for a hike? 
  1. Would you rather have to hunt and gather all of your food or eat McDonald’s for every meal? 
  1. Would you rather be a detective or a scientist? 
  1. Would you rather have fortune or fame? 
  1. Would you rather live in a remote destination or the heart of a metropolitan city? 
  1. Would you rather live a peaceful life in a small cabin in the woods or a drama-filled life in a mansion in a big city? 
  1. Would you rather have a pause or a rewind button in your life? 
  1. Would you rather find your soulmate or your calling? 
  1. Would you rather always have a full phone battery or a full gas tank? 
  1. Would you rather stay the age you are physically forever or stay the way you are now financially forever? 
  1. Would you rather stay in during a snow day or build a fort? 
  1. Would you rather be able to take back anything you say or hear any conversation that is about you? 
  1. Would you rather go back to the past and meet your loved ones who passed away or go to the future to meet your children or grandchildren to be? 
Would you rather never get a cold ever again or never be stuck in traffic ever again would you rather question
  1. Would you rather never get a cold ever again or never be stuck in traffic ever again? 
  1. Would you rather have a personal maid or a personal chef? 
  1. Would you rather have Beyoncé’s talent or Jay-Z‘s business acumen? 
  1. Would you rather be tall and average looking or three feet tall but beautiful? 
  1. Would you rather communicate only in emoji or never be able to text at all ever again? 
  1. Would you rather be an extra in an Oscar-winning movie or the lead in a box office bomb? 
  1. Would you rather be able to take back anything you say or hear any conversation that is about you? 
  1. Would you rather work the job you have now for a year at double your current rate of pay or have one year off with what you are making now? 
  1. Would you rather win $25,000 or your best friend win $100,000? 

Would You Rather Questions About Superpowers  

a woman at work smiling while asking would you rather questions about superpowers
  1. Would you rather have the ability to see 10 minutes into the future or 150 years into the future? 
  1. Would you rather be able to swim underwater limitlessly or fly? 
  1. Would you rather have telekinesis (the ability to move things with your mind) or telepathy (the ability to read minds)? 
  1. Would you rather have universal respect or unlimited power? 
  1. Would you rather detect every lie you hear or get away with every lie you tell? 
  1. Would you rather have telekinesis (the ability to move things with your mind) or telepathy (the ability to read minds)? 

Worst Case Scenario Would You Rather Questions  

two colleagues having fun asking each other worst case scenario would you rather questions
  1. Would you rather be too hot or too cold? 
  1. Would you rather be locked for a week in a room that’s overly bright or a room that’s totally dark? 
  1. Would you rather hear a comforting lie or an uncomfortable truth? 
  1. Would you rather be trapped in an elevator or stuck on a suspension bridge? 
  1. Would you rather hear holiday-themed music forever, or never heard it again? 
  1. Would you rather be in jail for five years or be in a coma for a decade? 
  1. Would you rather be chronically under-dressed or overdressed? 
  1. Would you rather have everyone you know be able to read your thoughts or for everyone you know to have access to your Internet history? 
  1. Would you rather have police hunting you down for a crime you didn’t commit or a serial killer actually hunting you? 
  1. Would you rather lose your sight or your memories? 
  1. Would you rather get a paper cut every time you turn a page or bite your tongue every time you eat? 
  1. Would you rather drink sour milk or brush your teeth with soap? 
  1. Would you rather labor under a hot sun or extreme cold? 
  1. Would you rather spend a year at war or a year in prison? 
Would you rather be in a zombie apocalypse or a robot apocalypse would you rather question
  1. Would you rather be in a zombie apocalypse or a robot apocalypse? 
  1. Would you rather lose your long-term memory or your short-term memory? 
  1. Would you rather give up your cellphone for a month or bathing for a month? 
  1. Would you rather lose the ability to read or lose the ability to speak? 
  1. Would you rather forget your partner’s birthday or your anniversary every year? 
  1. Would you rather be alone all your life or surrounded by really annoying people? 
  1. Would you rather be so afraid of heights that you can’t go to the second floor of a building or be so afraid of the sun that you can only leave the house on rainy days? 
  1. Would you rather listen to your least favorite song on a loop for a year or never listen to any music at all for a year? 
  1. Would you rather only be able to wash your hair twice a year or only be able to check your phone once a day? 
  1. Would you rather be asked the same question over and over again or never be spoken to ever again? 
  1. Would you rather never be able to keep anyone else’s secrets or have someone tell all of your secrets? 
  1. Would you rather be criticized or be ignored? 
  1. Would you rather sleep in a doghouse or let stray dogs sleep in your bed? 
  1. Would you rather be caught liking your ex’s Instagram pics or your partner’s ex’s Instagram pics? 
  1. Would you rather people knew all the details of your finances or all the details of your love life? 
  1. Would you rather always have an annoying song stuck in your head or always have an itch that you can’t reach? 

Would-you-rather questions are hilarious, but they aren’t the only questions you can ask to get to know your team better. Check out our list of the 300 best team building icebreaker questions for work which includes questions covering travel, music and movies, food, history, hobbies, holidays, and more. 

What are your favorite would-you-rather questions? Let us know in the comments section! 


Learn how team building activities can also help you get to know your colleagues in a deeper way.   

To find out how team building help teammates get to know each other, reach out to an Employee Engagement Consultant. 


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