🤔 150 Insanely Fun (and Head-Scratching) “Would You Rather” Questions in 2024

Would you rather keep surfing the web or start looking at the most perfect list of “Would You Rather” questions ever assembled?

“Would You Rather” questions are great icebreakers to help spark a conversation, stretch comfort zones, break down barriers, and make lasting memories in the process. They can even serve as a productive way to kick off a virtual team building game or group exercise.

🚨 Check out our curated list of virtual team building icebreakers and activities for more ways to leverage “This or That” questions with your team. 🚨

“Knowing each other is like music. What attracts us to them is their melody. And as we get to know who they are, we learn their lyrics” Click To Tweet

Whether you want to use “Would You Rather” questions for team building, loosen up meeting attendees or even warm up a conversation with guests while crashing a wedding, “This or That” questions will do the trick.

Without further ado, let’s dive into the best “Would You Rather”  questions for anyone in 2024! 

“Would You Rather” Questions for Work and Team Building

“Would You Rather” questions for work and team building are the ultimate go-to list for any kind of team bonding event. If  you want closer relationship between your employees, take a look at the cheat sheet below!

Get Your Free Would You Rather Questions Here

A) Fun  & Easy “This or That” Questions For Work & Team Building

“Who said work can’t be fun?”

1. Would you rather prepare your own lunch or have snack boxes delivered to your workplace?

• 🌟 Why this is a good “Would You Rather” question: This one is a no brainer! Be pampered or end up making a last- minute-sandwich for work?

2. Would you rather work in Los Angeles or in New York City?

• 🌟 Why this is a good “Would You Rather” question: Wish you could have New York nights and L.A. days.

3. Would you rather work an extra hour, but get an hour of break time or work with no breaks, but leave an hour earlier?

• 🌟 Why this is a good “Would You Rather” question: For the love of work, take a break!

4. Would you rather run a country or a business?

• 🌟 Why this is a good “Would You Rather” question: A great question to see how ambitious your team is.

5. Would you rather be the oldest person in the office or the youngest?

• 🌟 Why this is a good “Would You Rather” question: It’s all about productivity and getting s%*t done!

B) Hard & Thoughtful “This or That” Questions For Work & Team Building

“As if hard work isn’t enough..”

1. Would you rather be good at any new skill you try or work with the same skills and specialize in your work?

• • 🌟 Why this is a good “Would You Rather” question: Skill is a power not to be underestimated.

2. Would you rather have your dream job and be unable to retire in 50 years or have a terrible job but get to retire in 10 years?

• • 🌟 Why this is a good “Would You Rather” question: Depends on how much you love Mondays.

3. Would you rather have a terrible boss but a great job or a great boss but a terrible job?

• • 🌟 Why this is a good “Would You Rather” question: There’s only one right answer here: “My boss is the bomb!”

4. Would you rather do something you love and make just enough money to get by or do something you hate but make billions of dollars?

• • 🌟 Why this is a good “Would You Rather” question: Stuck between “I need to make money” and “I only live once”.

5. Would you rather be famous in your career field or celebrity famous?

• • 🌟 Why this is a good “Would You Rather” question: A little bit of fame never killed anyone.

C) Crazy & Weird “This or That” Questions For Work & Team Building

“For those who live dangerously”

1. Would you rather have an office where you could wear pajamas to work or work in a really fancy office?

• • 🌟 Why this is a good “Would You Rather” question: Workplace should feel like home, right?

2. Would you rather eat the oldest thing in the office fridge or clean the office bathroom with just toilet paper?

• • 🌟 Why this is a good “Would You Rather” question: This one goes to that truly dedicated employee!

3. Would you rather be friends with Oprah or Simon Cowell?

• • 🌟 Why this is a good “Would You Rather” question: Depends on whether you’d like to turn your wounds into wisdom or learn the best insults.

4. Would you rather have a name everyone misspells or a name everyone forgets?

• • 🌟 Why this is a good “Would You Rather” question: Two words: Name Tag 🔖.

5. Would you rather be stuck on an island for eternity all on your own or with someone you hate?

• • 🌟 Why this is a good “Would You Rather” question: Look at the bright side — you have a whole island for yourselves to stay out of each other’s way.  Also, would there be free wi-fi?

“Would You Rather” Questions For Icebreakers

“Would You Rather” questions for icebreakers will always be one of the best “Get to Know You” activities. From weird to fun, and everything in between, these questions will surely turn an icy cold atmosphere to a warm one.

A) Fun & Easy “This or That” Questions For Icebreakers

“Just play. Have fun.”

1. Would you rather be the funniest person or the smartest person in the room?

• • 🌟 Why this is a good “Would You Rather” question: Best of both worlds.

2. Would you rather be known for your intelligence or for your good looks?

• • 🌟 Why this is a good “Would You Rather” question: Sheldon Cooper 🤓  vs. Johnny Bravo 🕺 kind of question.

3. Would you rather have an unlimited gift card to a restaurant or a clothing store?

• • 🌟 Why this is a good “Would You Rather” question: This is a win/win situation.

4. Would you rather be on an airplane between two arguing passengers or sit next to a screaming infant?

• • 🌟 Why this is a good “Would You Rather” question: Airplane mode activated!

5. Would you rather have unlimited pizza 🍕  for life or unlimited tacos 🌮  for life?

• • 🌟 Why this is a good “Would You Rather” question: Two words — Food Coma

Pro-tip: Do you want to be more creative? Slip a list of the funniest and the best “Would You Rather” questions  into a curated care package from Caroo and send it to the person in question. Satisfy their taste buds and get them talking!

B) Hard & Thoughtful “This or That” Questions For Icebreakers

“Make it or break it”

1. Would you rather live forever or be remembered forever?

• • 🌟 Why this is a good “Would You Rather” question: The choice between being immortal and being immortalized is a tough one.

2.  Would you rather have one wish granted today or three wishes granted ten years from now?

• • 🌟 Why this is a good “Would You Rather” question: A visit by a genie in a bottle? Amen to that!

3. Would you rather have unlimited respect or unlimited power?

• • 🌟 Why this is a good “Would You Rather” question: Respect and Power could be game changers.

4. Would you rather be a kid your whole life or an adult your whole life?

• • 🌟 Why this is a good “Would You Rather” question: It all comes down to whether you want your inner child to grow up or not.

5. Would you rather live a long life in poverty or a short life with wealth?

• • 🌟 Why this is a good “Would You Rather” question: Quality vs. Quantity

C) Crazy & Weird “Would you Rather” Questions For Icebreakers  

“For the ones who like weird things”

1. Would you rather be completely bald or covered from head to toe with hair?

• • 🌟 Why this is a good “Would You Rather” question: Hair Goals!

2. Would you rather have out-of-control body hair or out-of-control body odor?

• • 🌟 Why this is a good “Would You Rather” question: Better than having an extra toe.

3. Would you rather babysit a crying infant for a day or have an unwanted houseguest for a week?

• • 🌟 Why this is a good “Would You Rather” question: How about babysitting a crying infant while your houseguest is around?

4. Would you rather be magical, but life on earth, or live in a magical land but be normal?

• • 🌟 Why this is a good “Would You Rather” question: You are magic, no matter what.

5. Would you rather live in a world where you dance instead of walk or sing instead of talk?

• • 🌟 Why this is a good “Would You Rather” question: Have dance-offs or sing-offs all the time? Yes, please!

“Would You Rather” Questions for Adults

“Would You Rather” questions for adults are perfect to ease tension and help communicate freely — especially if they’re meeting for the first time. Next time you’re in a room with someone, skip the small talk, and make use of the questions below.

Get Your Free Would You Rather Questions Here

A. Fun & Easy “This or That” Questions for Adults

“Because our inner child never gets old”

 1.  Would you rather have a completely automated home or a self-driving car?

• • 🌟 Why this is a good “Would You Rather” question: Such an easy question to answer. Ummm… Both?

2. Would you rather never be stuck in traffic again or never get another cold?

• • 🌟 Why this is a good “Would You Rather” question:  Non-stop sneezing while lying in bed with a box of “Kleenex” and Vitamin C next to you?  Traffic doesn’t seem too bad now, huh?

3. Would you rather live on the beach or in a cabin in the woods?

• • 🌟 Why this is a good “Would You Rather” question: Is a cabin or a treehouse at the beach an option 🏖?

4. Would you rather be completely invisible for one day or be able to fly for one day?

• • 🌟 Why this is a good “Would You Rather” question: A question that never gets old. Who wouldn’t want super powers?

5. Would you rather travel the world for a year, all expenses paid or have $40,000 to spend on whatever you want?

• • 🌟 Why this is a good “Would You Rather” question: The choice between making lasting memories and going on a shopping spree shouldn’t be that hard, should it?

Hey! Are you looking for a way to shout out one of your employees?

Check out CareCards — a great way to recognize your employee’s special moment with a colorful compilation of heartfelt messages from their fellow colleagues.

Caroo’s specially designed CareCards program is a FREE tool for distributed teams to celebrate any occasion in style! You can also order your lucky recipient a personalized gift from the team right off the Caroo gifting platform.

B. Hard & Thoughtful “This or That” Questions for Adults

“With adulthood comes decision-making”

1. Would you rather have super sensitive taste buds or super sensitive hearing?

• • 🌟 Why this is a good “Would You Rather” question: Losing a sense? Think again!

2. Would you rather lose all your money and valuables or lose all the pictures you have ever taken?

• • 🌟 Why this is a good “Would You Rather” question: Turns out money is not the only valuable thing in this world.

3. Would you rather be feared by all or loved by all?

• • 🌟 Why this is a good “Would You Rather” question: Let people be afraid of how much they love you.

4. Would you rather never get angry or never be envious?

• • 🌟 Why this is a good “Would You Rather” question: Tough question. You might control anger, but what about envy?

5. Would you rather donate your body to science or donate your organs to people who need them?

• • 🌟 Why this is a good “Would You Rather” question: A good deed is never wasted.

Pro-tip: Have everyone order in lunch at your next meeting with a digital lunch gift card from Caroo!

Check out gift cards here 👈

C) Crazy & Weird “This or That” Questions for Adults

“Who you callin’ crazy?”

1. Would you rather spend a year on Mars by yourself or party on a remote island with your friends?

• • 🌟  Why this is a good “Would You Rather” question: Do they serve tequila on Mars?

2. Would you rather speak to animals or speak 10 foreign languages?

• • 🌟 Why this is a good “Would You Rather” question: It’s all about the art of communication.

3. Would you rather lose your passport or smartphone?

• • 🌟 Why this is a good “Would You Rather” question: Depends on what you have saved on that smartphone 📱. Also can be a good segue into a round of Never Have I Ever questions.

4. Would you rather walk barefoot in a public restroom 🤢 or get poisoned 🤮?

• • 🌟 Why this is a good “Would You Rather” question: The sole purpose of this question is to see you cringe!

5. Would you rather be the hero that saved the girl or the villain that took over the world?

• • 🌟 Why this is a good “Would You Rather” question: Love versus Power is the ultimate dilemma.

Pro-tip: If you need more engagement ideas, check out The Assist. Each week they deliver actionable workplace culture, productivity and leadership inspo straight to your inbox for free.

“Would You Rather” Questions for Teens

“Would You Rather” questions for teens are every parent’s holy grail to get to know their teenager better. The questions below cover every teenager 一 the Entitled, the Know-it-all, the Rebel, the Melodramatic, the Quiet, the Idealist and so on.

A) Fun & Easy “This or That” Questions for Teens  

“That’s so lit”

1. Would you rather never play video games again or never use your favorite mobile app again?

• • 🌟  Why this is a good “Would You Rather” question:  A tech-related question to a teen never gets old.

2. Would you rather have to listen to only Justin Bieber or only Ariana Grande for the rest of your life?

• • 🌟  Why this is a good “Would You Rather” question: To choose between two super successful young artists should be an easy question to answer, right? 😉

3. Would you rather be an only child or have ten siblings?

• • 🌟  Why this is a good “Would You Rather” question: Family matters.

4. Would you rather eat out by yourself or eat at home with your family?

• • 🌟  Why this is a good “Would You Rather” question:  Is there a way to combine family quality time and “I need some me” time?

5. Would you rather be Prom King/Queen 👸🏻🤴🏼 or valedictorian 👩🏼‍🎓?

• • 🌟  Why this is a good “Would You Rather” question: Your friends could always answer this one for you.

B) Hard & Thoughtful “This or That” Questions for Teens

“Being a teenager has never been easy”

1. Would you rather someone read your diary or someone read your text messages?

• • 🌟 Why this is a good “Would You Rather” question: If your privacy or secrets were to be exposed, would it really matter how it happens?

2. Would you rather have nosy parents or strict parents?

• • 🌟  Why this is a good “Would You Rather” question: Accept their perfect imperfections.

3. Would you rather be popular, but have fake friends or be unpopular, but have real friends?

• • 🌟  Why this is a good “Would You Rather” question: It all depends on your priority list.

4. Would you rather sneak out of the house or miss a party that the most popular person in school invited you to?

• • 🌟 Why this is a good “Would You Rather” question: Why is teenage life so hard 😣?

5. Would you rather climb the highest mountains or swim the deepest seas?

• • 🌟  Why this is a good “Would You Rather” question: Challenge fearless and risk-taking teenagers.

C) Crazy & Weird “This or That” Questions for Teens

“OMG!”

1. Would you rather smell like onions or garlic?

• • 🌟 Why this is a good “Would You Rather” question: Nothing wrong with adding flavor to things.

2. Would you rather become an adult overnight or stay a teenager forever?

• • 🌟  Why this is a good “Would You Rather” question: Preparing a pros and cons list for this one might be helpful.

3. Would you rather prefer not having a cell phone ever again or not being able to gossip again 😳?

• • 🌟 Why this is a good “Would You Rather” question:  Ask this question and just wait for their reaction — Meltdown Alert!!

4. Would you rather talk like Darth Vader or speak in the language of the Middle Ages?

• • 🌟 Why this is a good “Would You Rather” question: Turn to the Dark Side…or not.

5. Would you rather be immortal on a mortal planet or be mortal on an immortal planet?

• • 🌟 Why this is a good “Would You Rather” question:  Makes you wonder if you’ll ever get enough of this life.

“Would You Rather” Questions for Kids

“Would You Rather” questions for kids are important to help children think critically, broaden their imagination, encourage them to be less timid, all while having a blast!

A) Fun & Easy “This or That” Questions for Kids

“I’m just a kid having fun”

1. Would you rather be a detective 🕵🏼  or a pilot 👨🏻‍✈️?

• • 🌟 Why this is a good “Would You Rather” question: A great question to have them think about their future goals and dreams.

2. Would you rather fly a kite or swing on a swing?

• • 🌟 Why this is a good “Would You Rather” question: Any outdoor activity is good for their tiny bodies and big souls.

3. Would you rather go skiing or go to a water park?

• • 🌟 Why this is a good “Would You Rather” question: This is a good way to have them talk about their hobbies.

4. Would you rather be a wizard 🧙🏼 or a superhero?

• • 🌟 Why this is a good “Would You Rather” question: One of the most confusing yet most thrilling questions to ask a kid.

5. Would you rather skip class or have a 2-hour-recess at school?

• • 🌟 Why this is a good “Would You Rather” question: The perfect way to find out if they enjoy school or not.

B) Hard & Thoughtful “This or That” Questions for Kids

“Think Critically”

1. Would you rather never have homework again or be paid to do your homework?

• 🌟 Why this is a good “Would You Rather” question: Who invented homework in the first place?!

2. Would you rather have a million dollars in pennies or a hundred million dollars worth of ice cream?

• 🌟 Why this is a good “Would You Rather” question: We scream ice-cream 🍦!

3. Would you rather be the smartest kid at your school or be the best kid at sports in your school?

• 🌟 Why this is a good “Would You Rather” question: You’re loved no matter what!

4. Would you rather have only one best friend for the rest of your life or have 10 best friends that live in other countries?

• 🌟 Why this is a good “Would You Rather” question: Kids are big on friendships.

5. Would you rather it’s Christmas every day or your birthday every day?

• 🌟 Why this is a good “Would You Rather” question: A birthday is practically Christmas for every kid 🎁.

C) Crazy & Weird “This or That” Questions for Kids

“Holy Moly!”

1. Would you rather be able to speak every language on Earth or communicate with aliens?

• 🌟 Why this is a good “Would You Rather” question: They might ask you if you could take them to the aliens 👽🛸

2. Would you rather be able to slide down rainbows or jump on the clouds?

• 🌟 Why this is a good “Would You Rather” question: Such questions are always exciting for kids.

3. Would you rather be able to visit the stars or discover a treasure on Earth?

• 🌟 Why this is a good “Would You Rather” question: Do they want to be an astronaut or the next Indiana Jones?

4. Would you rather have a giant tongue or giant feet?

• 🌟 Why this is a good “Would You Rather” question: Expect the unexpected.

5. Would you rather eat rotten eggs or drink sour milk?

• 🌟 Why this is a good “Would You Rather” question: Trying new and weird things is one thing that kids love.

“Would You Rather” Questions for Couples

“Would You Rather” questions for couples can turn a stay-in night into a fun, intimate and enlightening one. How well do you know each other? There’s only one way to find out.

Get Your Free Would You Rather Questions Here

A) Fun  & Easy “This or That” Questions For Couples 

“Lovin’ you is fun”

1. Would you rather exercise together or watch a movie together?

• 🌟 Why this is a good “Would You Rather” question: Anything sounds good when you’re together.

2. Would you rather scream at each other or give each other the silent treatment?

• 🌟 Why this is a good “Would You Rather” question: Good question to test each other’s problem-solving skills 🤔.

3. Would you rather go out for date night or do date night at home?

• 🌟  Why this is a good “Would You Rather” question: Remember — date night is the best night of the week. Spice up that love life 🔥.

4. Would you rather have a kiss every day or a hug every day?

• 🌟 Why this is a good “Would You Rather” question: Never let affection go unexpressed.

5. Would you rather go on a fun date or be given an expensive gift?

• 🌟 Why this is a good “Would You Rather” question: Isn’t a fun date the best gift ever?

B) Hard & Thoughtful “This or That” Questions For Couples 

“We’re in this together”

1. Would you rather tell a lie for a good reason or tell the truth for a bad reason?

• • 🌟 Why this is a good “Would You Rather” question: Do you believe in white lies?

2. Would you rather have your heart broken or be the heartbreaker?

• • 🌟 Why this is a good “Would You Rather” question: A broken heart is never a good thing 💔.

3. Would you rather have more time or more money?

• • 🌟 Why this is a good “Would You Rather” question: Every millennial’s dilemma.

4. Would you rather love your partner more or have them love you more?

• • 🌟 Why this is a good “Would You Rather” question: Too much love never hurt anyone.

5. Would you rather be a leader or a follower?

• • 🌟 Why this is a good “Would You Rather” question: Think well about the balance of power here ⚖️.

C) Crazy & Weird “This or That” Questions For Couples

“I’m crazy about you”

1. Would you rather give up bathing for a month or give up the internet for a month?

• • 🌟 Why this is a good “Would You Rather” question: Ask your partner which one they would be ok-ish with.

2. Would you rather find your true love or find a suitcase with 5 million dollars inside?

• • 🌟 Why this is a good “Would You Rather” question: Isn’t true love priceless?

3. Would you rather have a golden voice or a silver tongue?

• • 🌟 Why this is a good “Would You Rather” question: “All that glitters is not gold” ✨.

4. Would you rather live with your partner in one town or be single and tour Europe?

• • 🌟 Why this is a good “Would You Rather” question: Taste love or taste adventure?

5. Would you rather live to 150 but have a boring life or live to 50 but have a really exciting life?

• • 🌟 Why this is a good “Would You Rather” question: Time stops when you’re with the one you love.

“Would You Rather” Questions for Him

“Would You Rather” questions for him is every girl’s chance to dig deep and find out more and more about the man she loves. The question is: Will your man crack or will he be up for it?

Get Your Free Would You Rather Questions Here

A) Fun & Easy “This or That” Questions for Him

“Bring them on!”

1. Would you rather go watch a movie or go watch the sunset?

• • 🌟 Why this is a good “Would You Rather” question: You might be surprised by what your partner prefers.

2. Would you rather cuddle under the stars or cuddle under a blanket?

• • 🌟 Why this is a good “Would You Rather” question: As long as he gets to cuddle with you, it doesn’t really matter. Unless it’s really cold outside?

3. Would you rather sing to your partner or play him a song on a musical instrument?

• • 🌟 Why this is a good “Would You Rather” question: Make sure not to get teardrops on your guitar 🎸.

4. Would you rather cook dinner with your partner or have your partner cook dinner for you?

• • 🌟 Why this is a good “Would You Rather” question: It’s always a good idea to test their culinary skills.

5. Would you rather go out for fine dining or order pizza and watch Netflix?

• • 🌟 Why this is a good “Would You Rather” question: If it’s the first date, choose wisely.

B) Hard & Thoughtful “This or That”  Questions for Him

“It takes a tough man to make choices”

1. Would you rather cheat or be cheated on?

• • 🌟 Why this is a good “Would You Rather” question: Next question please!

2. Would you rather have someone tell you the brutal truth or have them lie to protect your feelings?

• • 🌟 Why this is a good “Would You Rather” question: Is honesty always the best policy?

3. Would you rather all the chats on your phone leak or all the photos?

• • 🌟 Why this is a good “Would You Rather” question: Yikes! But an honest man has nothing to worry about.

4. Would you rather be happy, wealthy, or healthy?

• • 🌟 Why this is a good “Would You Rather” question: This will spark an interesting conversation.

5. Would you rather forgive or forget?

• • 🌟 Why this is a good “Would You Rather” question: Learn more about his heart.

C) Crazy & Weird “This or That”  Questions for Him

“For the wild & crazy”

1. Would you rather take a vow of silence or a vow of celibacy for your entire life?

• • 🌟 Why this is a good “Would You Rather” question: Vows can be intimidating. Does anyone disagree?

2. Would you rather get stuck in an elevator with your ex or with your partner and their ex?

• • 🌟 Why this is a good “Would You Rather” question: “Awkward” doesn’t even begin to describe the situation.

3. Would you rather be criticized or ignored?

• • 🌟 Why this is a good “Would You Rather” question: Ignore this question.

4. Would you rather marry someone who doesn’t love you or marry someone you do not love?

• • 🌟 Why this is a good “Would You Rather” question: What’s your stance on “Marriage for Reason” 👰🏻‍♀️🤵🏻?

5. Would you rather have to kiss every person you meet or never kiss your partner again?

• • 🌟 Why this is a good “Would You Rather” question: Beware of tricky questions!

“Would You Rather” Questions for Her

“Would You Rather” questions for her will let women step out of their comfort zone, communicate openly, and unexpectedly surprise you. Ready, set, go!

Get Your Free Would You Rather Questions Here

A) Fun & Easy “This or That” Questions for Her

“Girls just wanna have fun!”

1.Would you rather have breakfast in bed or a midnight snack?

• • 🌟 Why this is a good “Would You Rather” question: Depends if you’re an early bird or a night owl.

2. Would you rather read a romantic novel together or watch a romantic movie together?

• • 🌟 Why this is a good “Would You Rather” question: Read the Notebook or watch Ryan Gosling be the perfect Noah?

3. Would you rather slow dance with your partner or dance to a fast beat?

• • 🌟 Why this is a good “Would You Rather” question: Maybe you can be her Patrick Swayze?

4. Would you rather write a love letter or get a love letter 💌?

• • 🌟 Why this is a good “Would You Rather” question: We want love letters back!

5. Would you rather give up dates or kisses?

• • 🌟 Why this is a good “Would You Rather” question: What makes you feel closer to your partner?

B) Hard & Thoughtful “This or That” Questions for Her

“Thinking begins when you ask really difficult questions”

1. Would you rather be in an unbalanced relationship where you love them more or they love you more?

• • 🌟 Why this is a good “Would You Rather” question: Relationship questions are always so complicated! Can’t we just love each other unconditionally?

2. Would you rather be with a jealous partner or a distant one?

• • 🌟 Why this is a good “Would You Rather” question: Depends on whether you think jealousy is a sign of love or lack of trust.

3. Would you rather meet the love of your life in high school or at the age of 30?

• • 🌟 Why this is a good “Would You Rather” question: Finding true love is rare, so whenever you do, just don’t let go.

4. Would you rather outlive your partner or have them outlive you?

• • 🌟 Why this is a good “Would You Rather” question: This one might make you feel uncomfortable and emotional, but that’s the whole point.

5. Would you rather you out-earn your partner or have them out-earn you?

• • 🌟 Why this is a good “Would You Rather” question: Let’s talk about 💵 💰.

C) Crazy & Weird “This or That”  Questions for Her

“Bats%*t Crazy”

1. Would you rather have a skin that changes color based on your emotions or tattoos that appear all over your body whenever you are dishonest?

• • 🌟 Why this is a good “Would You Rather” question: Pass!

2. Would you rather have quintuplets or have no kids?

• • 🌟 Why this is a good “Would You Rather” question:  Quin..Quin… Quintupwhat 😱?!

3. Would you rather have a spouse that chews loudly or spits when they talk?

• • 🌟 Why this is a good “Would You Rather” question: Ew! But, hey, true love is supposed to be unconditional.

4. Would you rather find out your partner hates dogs or that they cheated on their ex?

• • 🌟 Why this is a good “Would You Rather” question: Hmmm… a dog hater or a cheater? Choose the lesser evil.

5.  Would you rather date someone with their ex’s name tattooed on their chest or date someone whose ex lives next door?

• • 🌟 Why this is a good “Would You Rather” question: There’s no way to get rid of that ghost, huh?

“Would You Rather” Questions for Friends

“Would You Rather” questions for friends will spice up game night and make it no less than epic! Now, throw away the board games!

Get Your Free Would You Rather Questions Here

A) Fun & Easy “This or That” Questions For Friends

“I’d take a Nerf bullet for you my friend”

1. Would you rather have a time machine or a teleportation device?

• • 🌟 Why this is a good “Would You Rather” question: Who wouldn’t love to have both?

2. Would you rather listen to an annoying laugh for a whole day or get tickled for one hour?

• • 🌟 Why this is a good “Would You Rather” question: Remember their answer next time they get on your nerves 😈.

3. Would you rather be braver than most people or be able to fly?

• • 🌟 Why this is a good “Would You Rather” question: Flying itself needs courage, right?

4. Would you rather be trapped in a romantic comedy with your enemies or trapped in a horror tv show with your friends?

• • 🌟 Why this is a good “Would You Rather” question: Depends on how long the show is.

5. Would you rather give up social media or eat the same dinner for the rest of your life?

• • 🌟 Why this is a good “Would You Rather” question: Let’s see if there’s anything that’ll bring social media down!

B) Hard & Thoughtful “This or That” Questions For Friends

“That’s what good friends are for”

1. Would you rather relive the same day repeatedly for a year or lose a year of your life?

• • 🌟 Why this is a good “Would You Rather” question: Sparks interesting discussions about time and choices.

2.  Would you rather lose all of the money you’ve earned this year or lose all of the memories you’ve gained this year?

• • 🌟 Why this is a good “Would You Rather” question: We bet this past year made you set your priorities straight.

3. Would you rather lose all of your friends but win the lottery or keep your friends and stay broke?

• • 🌟 Why this is a good “Would You Rather” question: Sometimes money and friends don’t mix.

4. Would you rather never age physically or never age mentally?

• • 🌟 Why this is a good “Would You Rather” question: Never age at all?

5. Would you rather be able to change the future or change the past?

• • 🌟 Why this is a good “Would You Rather” question: Imagine the things you could  do with that kind of power!

C) Crazy & Weird “This or That” Questions For Friends

“Match my level of crazy”

1.  Would you rather be able to see 10 minutes into your own future or be able to see someone else’s entire future anytime you want?

• • 🌟 Why this is a good “Would You Rather” question: Depends on whether you like to live in the present or be the next Nostradamus.

2. Would you rather have a weird-looking smile or a weird-sounding laugh?

• • 🌟 Why this is a good “Would You Rather” question: Weird is the new charming.

3. Would you rather be filthy rich and live 400 years ago or be poor but live today?

• • 🌟 Why this is a good “Would You Rather” question: There’s no such thing as too many 💰-related questions.

4. Would you rather spend a year as a cop or as a teacher in an inner-city neighborhood?

• • 🌟 Why this is a good “Would You Rather” question: You are brave no matter what, my friend. Respect to you!

5.  Would you rather live the rest of your life as a monk or followed continuously by paparazzi?

• • 🌟 Why this is a good “Would You Rather” question: Is it easy to avoid paparazzi? Yes, if live and think like a monk.

Best “Would You Rather Questions”

These “Would You Rather Questions” are perfect for your next gathering with friends and family or even as team-building icebreakers.

A) Best Fun & Easy “This or That” Questions

“Let the games begin!”

1. Would you rather spend a week in the forest or a night in a real haunted house?

• • 🌟 Why this is a good “Would You Rather” question: No tropical resort?

2. Would you rather always have a full phone battery or a full gas tank?

• • 🌟 Why this is a good “Would You Rather” question: There’s always Uber to count on.

3. Would you rather win on Survivor or on The Bachelor or The Bachelorette?

• • 🌟 Why this is a good “Would You Rather” question: Winning at anything is always fun!

4. Would you rather sip gin with Ryan Reynolds or shoot tequila with Dwayne “The Rock” Johnson?

• • 🌟 Why this is a good “Would You Rather” question: Let us overthink this!

5. Would you rather shoot hoops with LeBron James or toss a football with Tom Brady?

• • 🌟 Why this is a good “Would You Rather” question: Who is a better coach?

 

B) Best Hard & Thoughtful “This or That” Questions

“Questions worth thinking about”

1. Would you rather have to save your annual salary and never use anything from it or give half of it to charity?

• • 🌟 Why this is a good “Would You Rather” question: Start with “How to save money 101”!

2. Would you rather work in an office where you’re paid per hour or per task completed?

• • 🌟 Why this is a good “Would You Rather” question: Hourly rate vs. Number of tasks

3. Would you rather be able to take back anything you say or hear any conversation that is about you?

• • 🌟 Why this is a good “Would You Rather” question: Maybe both?

4. Would you rather be able to read minds or be able to see the future?

• • 🌟 Why this is a good “Would You Rather” question: Depends on whether you want to live in the present or not…

5. Would you rather spend months in search of your dream job or be employed quickly for a mediocre job?

• • 🌟 Why this is a good “Would You Rather” question: Maybe have a mediocre job while searching for the dream job?

 

C) Best Crazy & Weird “This or That” Questions

“Crazy is subjective….”

1. Would you rather be in history books for something terrible or be forgotten completely after you die?

• • 🌟 Why this is a good “Would You Rather” question: Be in history books for something terrific instead!

2. 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?

• • 🌟 Why this is a good “Would You Rather” question: Wish you could have them all gathered together.

3. Would you rather detect every lie you hear or get away with every lie you tell?

• • 🌟 Why this is a good “Would You Rather” question: What about trying honesty?

4. Would you rather give your parents or your boss access to your browser history?

• • 🌟 Why this is a good “Would You Rather” question: Would rather clear that browser history…

5. Would you rather nobody remembers who you are at your 20-year class reunion or have everybody comment on how old you look?

• • 🌟 Why this is a good “Would You Rather” question: As long as you get to see old classmates, who cares?

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Would You Rather Questions Categories

If you are looking to create your own “would you rather” question, you can start from a list of categories to get your brainstorm started. The best would you rather question topics pull from relatable categories that the person you are asking can relate to. Commonly, this includes a topic that is familiar with room to have a conversation. I put together a few ideas to get you started crafting your next question:

1) Sports

• Example: Would you rather have your favorite team win the Super Bowl or throw the first pitch in a World Series game?

2) Movies

• Example: Would you rather learn the ways of the Jedi or study at Hogwarts?

3) Music

• Example: Would you rather go backstage at your favorite artist’s concert or hear your favorite song from them in their set?

4) Books

• Example: Would you rather never be able to read the same book twice or have to read the same book every year in January?

5) Deserted Island Scenario

• Example: Would you rather be stranded on a tropical island with your entire family or just one person?

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People Also Ask These Questions About “Would You Rather” Questions

1. What are “Would You Rather” questions?

• A: “Would You Rather” questions are great conversation starters that help you get to know people in ways you’ve never imagined you would.

2. What are the benefits of asking a “Would You Rather” question?

• A: “Would You Rather” questions promote team building and communication skills, decrease tension, and keep everyone engaged.

3. What are some funny “Would You Rather” questions?

• A: Funny “Would You Rather” questions are questions that oftentimes put people in ridiculous scenarios.

4. When should I use a “Would You Rather” question?

• A: “Would You Rather” questions can be used as an icebreaker game for a team bonding event, a gathering with friends or family, or during meetings and conferences.

5.  How are “Would You Rather” questions useful for work?

• A: “Would You Rather “ questions ease work stress, help team members get to know each other better; and strengthen relationships between team members.