120 Funny Would You Rather Icebreakers That Your Team Will Love

Ruth Hadari
Ruth Hadari
Agile Advocate, Engineering Ops Expert
Posted on
Nov 11, 2022
Updated on
Nov 11, 2022
Table of Content

Would You Rather questions are fun and easy icebreakers to help your team get to know each other at work, for fun or any other environment. Oftentimes in retrospective meetings, there are tensions between team members, or an unwillingness for team members to share, so breaking the ice upfront can be beneficial in improving team dynamics and facilitating more effective collaboration.

As trivial as they may appear, icebreaker games can greatly contribute to the development of a better work culture and foster employee trust. According to a survey of over 4,000 professionals, 63% believe that trust at work must be earned and that a lack of workplace relationships and trust can negatively affect productivity.

What Are Would You Rather Questions?

Would You Rather questions provide a fun way to learn more about someone or to pass the time. They can be used to break the ice at a party and also make for interesting icebreaker questions in the workplace.

By asking someone Would You Rather questions, you can learn about their likes, dislikes, and preferences, and you may even learn about their culture as well. No matter the type, these questions are always interesting to answer and are sure to engage a group. They can be light and fluffy or revealing, deep, and thought-provoking.

These activities are a way to have fun and laugh, but on a deeper level, they promote collaboration and improve productivity among colleagues. 

Why Are Would You Rather Questions Effective?

Would You Rather icebreaker questions are effective because they "break the ice" in any situation and require little preparation. In the workplace, they can be a tool for problem-solving, help employees learn more about one another, build team rapport, and identify potential problem areas.

Participants can identify which criteria are most relevant to them when making assessments and learn more about each other's working styles. Having this information can be valuable in fostering employee relationships and gaining a better understanding of a team's dynamics. When you understand the perspectives and mindset of the people you work with you will always work together better.

When done right, Would You Rather icebreakers are not only a great way to pass the time and break tension, but they can also engage the team in a way that can result in better decision-making. 

How to Ask Would You Rather Questions?

When it comes to socializing, few things are as enjoyable as asking Would You Rather questions. This type of icebreaker is the perfect way to get to know someone better and create meaningful discussions, but it also leads to some hilarious conversations!

If you’re looking for a clever way to liven up your meeting, here are the steps on how to ask Would You Rather questions:

  1. Set a clear goal for the meeting - Understanding the purpose of your meeting can help you choose the right icebreaker.
  2. List down Would You Rather questions that encourage fun and relevant discussions - Try to strike a balance between establishing a fun and informative icebreaker.
  3. Ask the team in a game format - If you’re playing with a group, each person can take turns answering the questions. If you’re asking questions individually, let the other person pick which one to answer.
  4. Set a timer (optional) - A timer can facilitate a more well-rounded answer if the meeting is on a tight schedule.
  5. Keep the conversations flowing - When one answer ends, let another question begin. A question should also be open-ended so that a conversation can follow.

While the primary goal is to ease team tension and encourage collaboration, you can gain valuable insight from the answers your team provides. So, be sure to actively listen and take notes as well.

120 Would You Rather Questions:

You're in luck because we've done the work and have put together a list of the best Would You Rather questions that will instantly engage your team.. 

From funny to hard, fun, crazy, and juicy, this list of 120 Would You Rather Questions covers it all. No matter which question you choose, you will be sure to capture the imagination and attention of your team.

20 Funny Would You Rather Questions

Are you looking for lighthearted and hilarious conversations? Having a good laugh can be a fun way to start off the meeting on a light note. 

  1. Would you rather have a pet skunk or a pet raccoon?
  2. Would you rather be always itchy or always sweaty?
  3. Would you rather be tissue paper or toilet paper?
  4. Would you rather eat dirt or drink vinegar?
  5. Would you rather have a tail or horns?
  6. Would you rather be able to fly or have invisibility?
  7. Would you rather have X-ray vision or the ability to see through walls?
  8. Would you rather be able to breathe underwater or walk on water?
  9. Would you rather have a million dollars or be able to fly?
  10. Would you rather be able to swim like a fish or run like a cheetah?
  11. Would you rather be really smart or really strong?
  12. Would you rather be able to stop time or teleport anywhere?
  13. Would you rather have a mansion with a private beach or a million dollars?
  14. Would you rather never have to sleep again or never have to eat again?
  15. Would you rather always feel hot or always feel cold?
  16. Would you rather have a giant head or a tiny body?
  17. Would you rather live forever or die and come back as a ghost?
  18. Would you rather give up shampoo or toothpaste?
  19. Would you rather lose your wallet or your phone?
  20. Would you prefer having ten siblings or being the only child?

20 Hard Would You Rather Questions

Do you want to challenge your team with some hard dilemmas? They will be scratching their heads for sure.

  1. Would you rather have a difficult life but be happy or an easy life and be unhappy?
  2. Would you rather have everything you want but no one to share it with, or have people you love but not everything you want?
  3. Would you rather know all the answers to life's questions, or never stop wondering about them?
  4. Would you rather be able to read people's thoughts, or have the power to control their thoughts?
  5. Would you rather always know the truth, or always feel happy?
  6. Would you rather be able to control the elements, or be able to heal any wound?
  7. Would you rather know the future, or have the ability to manipulate time?
  8. Would you rather have strict parents or neglectful parents?
  9. Would you rather ban or keep the death penalty?
  10. Would you rather get married for love or for immense wealth?
  11. Would you rather experience a short, intense pain or a long, drawn-out pain?
  12. Would you rather be completely alone in the world or constantly surrounded by people who hate you?
  13. Would you rather have an unlimited supply of delicious food but be unable to eat it, or an unlimited supply of nasty food but able to consume as much as you like?
  14. Would you rather succeed at your dream job interview or date the hottest person you know?
  15. Would you rather live in a real haunted house or live alone on an island?
  16. Would you rather give up social media or eat the same meal for the rest of your life?
  17. Would you rather be recognized throughout your life as the most liked or as the most accomplished person?
  18. Would you rather be in the Wizarding World or Middle-Earth? 
  19. Would you rather know when you will die or how you will die?
  20. Would you rather be unable to lie or believe everything you hear?

20 Fun Would You Rather Questions

A Would You Rather icebreaker does not have to be intense and can be simply fun. Make a positive start to the meeting with these questions.

  1. Would you rather meet someone on a blind date or on a dating app?
  2. Would you rather smell like garlic or wet dog?
  3. Would you rather be a supervillain or a superhero?
  4. Would you rather speak like Yoda or sound like Darth Vader?
  5. Would you rather fight twenty duck-sized bears or two bear-sized ducks?
  6. Would you rather never be able to wear clothes again or never be able to use electronics again?
  7. Would you rather have unlimited travel without money or have unlimited money but never get to travel?
  8. Would you rather be super hairy or completely bald?
  9. Would you rather go to the mountains or to the sea?
  10. Would you rather always sound like a chipmunk or always sound like Donald Duck?
  11. Would you rather be a wizard or a superhero?
  12. Would you rather celebrate Christmas every day or your birthday every day?
  13. Would you rather have a fun date or receive an expensive gift?
  14. Would you rather stop bathing for a month or stop using internet for a month?
  15. Would you rather sing well or dance well?
  16. Would you rather live to 200 and have a normal life, or live to 50 and have an extraordinary life?
  17. Would you rather have your true love or a million dollars at your door today?
  18. Would you rather kiss everyone you meet or never kiss your loved one again?
  19. Would you rather be clever or funny?
  20. Would you rather lose your ability to read or never hear music again?

20 Crazy Would You Rather Questions

Want to keep your team on edge and get their full attention? Get them thinking with these crazy Would You Rather questions.

  1. Would you rather know everyone's deepest darkest secret, or be able to cure any disease?
  2. Would you rather live in a world without music or a world without books?
  3. Would you rather be able to speak any language fluently or be able to teleport anywhere you want?
  4. Would you rather be the best at anything you do, or have a perfect life with no challenges?
  5. Would you rather be always a bit late or very early all the time?
  6. Would you rather own a private jet or a robot maid?
  7. Would you rather dance salsa or ballet?
  8. Would you rather chew loudly or spit when you speak?
  9. Would you rather have a pet cat or a pet dog?
  10. Would you rather be trapped in an adventure movie with your enemies or in a horror movie with your friends?
  11. Would you rather be able to know the future or change the past?
  12. Would you rather miss out on a year of your life or live the same day every day for a year?
  13. Would you rather live in LA or New York?
  14. Would you rather be President of a country or CEO of a giant corporation?
  15. Would you rather be a famous celebrity or be the most established in your career?
  16. Would you rather have unlimited pizza or unlimited burgers?
  17. Would you rather live your entire life as a kid or as an adult?
  18. Would you rather show your browser history to your parents or your boss?
  19. Would you rather know what people are saying about you or be able to take back anything you said?
  20. Would you rather have unlimited power or be forever respected?

20 Juicy Would You Rather Questions

Want to liven up the room and raise the stakes? We've got some juicy Would You Rather questions that'll get the conversation started.

  1. Would you rather have a job that helps a lot of people but doesn't make much money or a job that is morally questionable but makes a lot of money?
  2. Would you rather have a normal date night every week or a special date night every month?
  3. Would you rather date someone who loves pets or someone who doesn't?
  4. Would you rather be the heartbreaker or have someone break your heart?
  5. Would you rather accidentally text your boss a dirty message or leave a sexy voicemail to your mom?
  6. Would you rather die before or after your spouse?
  7. Would you rather kiss your celebrity crush or get paid $1,000?
  8. Would you rather get a job promotion or sleep with your crush?
  9. Would you rather live five minutes from a mediocre job or travel two hours to your dream job?
  10. Would you rather work shorter hours but more work days or longer hours but fewer work days?
  11. Would you rather your texts or your photos be leaked in the workplace?
  12. Would you rather win $250,000 on your own or have your best friend win $1,000,000?
  13. Would you rather have kids or adopt?
  14. Would you rather live alone on an island for a year or go six months without making love?
  15. Would you rather have your parents arrange your marriage or marry your ex?
  16. Would you rather be the most demanding person or the most boring person?
  17. Would you rather be charged $10 every time you insult someone or lie to them?
  18. Would you rather earn $50 million through hard work and dedication or simply inherit $10 million?
  19. Would you rather have millions of dollars and a life filled with drama or be poor and live a peaceful life?
  20. Would you rather never be able to say "I love you" to anyone, or have to say it to everyone?

20 Would You Rather Questions For Work

Would You Rather questions for work meetings can engage team members, and work-related conversations can help your team understand each other's work ethics.

  1. Would you rather have a lot of responsibility or very little responsibility?
  2. Would you rather work in an office or work from home?
  3. Would you rather have a higher set salary or be able to earn commissions?
  4. Would you rather have a boss or be your own boss?
  5. Would you rather deal with people or numbers?
  6. Would you rather work with things or with people?
  7. Would you rather be paid all at once, including benefits, for the year or little by little during the year?
  8. Would you rather ride a bicycle or drive to work?
  9. Would you rather dance or sing in front of your team?
  10. Would you rather be part of a small team or a large team?
  11. Would you rather partner with Elon Musk or Jeff Bezos to launch your own business?
  12. Would you rather be dressed in your pajamas or in a suit at work?
  13. Would you rather have the best unlimited coffee or the best unlimited pantry snacks?
  14. Would you rather attend meetings all day or work at a desk all day?
  15. Would you rather follow a set routine or work on different tasks every day?
  16. Would you rather work with little supervisory feedback or receive regular feedback from your boss?
  17. Would you rather work all day in a noisy environment or in a very quiet space?
  18. Would you rather own your own company and retire at 30 or work for someone else and retire at 60?
  19. Would you rather work that requires you to move around all day or a job that requires you only sit at your desk?
  20. Would you rather remain in your city or have the opportunity to work abroad?

Conclusion

Would You Rather icebreakers are an important part of the workplace because they help the team get to know each other better. These can also help break the ice, especially with tense meetings. By getting to know each other better, team members can build trust and be more productive.

Our blog page provides insightful guides for conducting a successful retrospective meeting with your team and ways to make the most of your team's potential.

For your next retrospective, check out GoRetro, the ultimate agile retrospective tool that may be exactly what you need.

About the author

Ruth Hadari
Agile Advocate, Engineering Ops Expert

Highly experienced in leading multi-organizational teams, groups, in-shore as well as off-shore. The go-to person who is able to simplify the complex. An agile advocate, experienced in all common methodologies. Responsible for the entire software development lifecycle process from development, QA, DevOps, Automation to delivery including overall planning, direction, coordination, execution, implementation, control and completion. Drives execution, and communicates on status, risks, metrics, risk-mitigation and processes across R&D.

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