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27 Extra Killer Would You Rather Questions - The Best List You Need Now

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Jasper is our expert conversationalist and wordsmith. He loves coming up with questions, jokes, and topics designed to create natural conversation. His work has been featured on Marriage.com, iHeart Media, Elite Dai ...
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by | | January 27, 2022


Would You Rather questions can zap boredom in an instant. On our site here, you'll find all the best conversation starters to instantly make any dull conversation delightfully engaging.

I have written over a hundred of articles on fun questions to ask - all of which I have used personally. They've all helped me and I know they'll help you too.

Ready for that instant serotonin boost? Let's go!

Contents

What is Would You Rather?

Would You Rather is a set of questions that pose a dilemma, often used as a party game or event icebreakers. They range from simple to more complex dilemma questions and cover almost any topic.

It is considered a simple, non-intrusive way of getting a peek at the funny, naughty, or unusual side of people. Two options or scenarios are provided, and answering ‘neither,’ or ‘both’ is unacceptable. The fun continues as participants get into a debate.

Ultimate List Of Would You Rather Questions

Not all trivia questions are created the same. Some make you think more while others just give you that opportunity to be silly - in a good way. How and when you ask them may depend on the impressions you may already have on your date. Switch the questions up for more variety and be ready to get an extra slice of the other person's personality.

Questions Categories

6 Easy Would You Rather Questions You Can Use In Any Conversation

In general, asking questions is an excellent way to convey engagement. Start it off just light and easy. A set of uncomplicated questions is quite like an appetizer - take a few bites, and you know you’d end up wanting for more. Easy questions take the pressure off participants and are generally not emotionally taxing. Not everyone is gifted in carrying out conversations fluidly and easily. However, these easy questions can lay the groundwork for conversation that can last for an entire day or night.

Here are 6 easy and fun would you rather questions you can use:

1. Would You Rather Have Nosy Parents or Strict Parents?

Asking family-related questions is a big no-no for many. However, questions like this often offer a small window to what kind of family life the person answering it has. And more importantly, you’d know what kind of parent one envisions to be.

2. Would You Rather Be a Wizard or Superhero?

Harry Potter or Captain America? Daniel Radcliffe vs. Chris Evans? Not always an easy question, but a sure-fire way to make everyone giggle right away. It’s always a matter of interest. Girls would likely enjoy answering this more than their male counterparts.

3. Would You Rather Skip Class or Have a 2-hour Class Break at School?

Trust me- anyone might take a while to answer this question. In reality, this would make you think hard as well. You can also back it up with a question about what kind of student the other person was back in the day. You can ask them about what they'd do if they had a break that long. Would you go and watch Star Wars while eating some ice cream? Would you take a nap? Either way, you'll see what the other person likes to do when they have free time.

4. Would You Rather Never Have Homework Again or Be Paid to Do Your Homework?

Who likes homework anyway? But getting paid to do it might just put some interest in there. See what your date thinks about it. Maybe it would be a stretch, but you'll see if your date is willing to do uncomfortable things if they can get something valuable in return. It's a fun way to see if he will care for you enough to go through anything, as long as he has you.

5. Would You Rather Be the Brightest Student in School or the Best in Sport Kid?

While you might go for a Straight-A student, your date may have a different opinion. Ask him why right away, and you'd probably get more than you asked for - his favorite sport, player, etc. You'd learn a lot about your partner if you knew what they were like as a child.

6. Would You Rather Have a Giant Tongue or Giant Feet?

This might sound silly but getting your date to react to this is a big win. Any question game is good to try if you want to get a unique and fun conversation out of your time together. And a question like this, well, it will definitely get him talking. After all, choosing between a giant tongue or giant feet is something that people don't usually think about.

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5 Funny Questions To Ask For A Great Would You Rather Game

Simple is good, but funny is better - at least when it comes to your choice of questions. Cracking jokes or injecting funny questions diffuses stress for both of you and enlivens the atmosphere. It's an excellent way to stir away from the usual 'How's the weather?' or 'How's work?' kind of conversation. Boring dates are such a big red flag, so save yourself from being labeled as not-so-interesting. Build rapport and chuckle more.

Here are 5 funny would you rather questions:

7. Would You Rather Listen to an Annoying Laugh or Be Tickled for the Rest of Your Life?

This got me thinking as well. I can endure Janice's laugh from Friends but won't probably be able to stand getting tickled in my entire lifetime. It would be a fun game to try it out with him, though. Think of your most annoying laugh and let him hear it. After that, tickle him until he curls up into a ball and asks you to stop. See which one he can endure, and you'll know his answer.

8. Would You Rather Have a Face that Everyone Laughs at or a Name that Everyone Laughs At?

There will be no need for question cards because this question will definitely start a great conversation. This is a question that is borderline funny and difficult. It'd be interesting to listen to the choice and the justification that comes with it. I bet he'd pick the name, but we'll never know, right?

9. Would You Rather be Only Able to Laugh or be Able to Shout?

See if his sense of humor could stand not being able to laugh. Or, you can find out if his wild sense of adventure can withstand not being able to shout. Try asking him this when you have a date at an amusement park. You'll probably know the answer by how much he laughs or shouts while you're there. Still, it's a great question to ask.

10. Would You Rather Go a Year with No Eyelashes or Go a Year with No Eyebrows?

Trust me - this is pretty much a tricky question for anyone. Truly lush lashes and eyebrows that wow are a must. So, find out which eye hair he can live without. Either way, it will look really weird. Find out which one he can live with (or without!).

11. Would You Rather Have to Make a One-Minute Speech in Front of 10,000 People or Have to Kiss a Frog?

But what if the latter turns out to be a prince? Questions like these can always get a person thinking. A crazy scenario involving choosing between these two things will get him to talk about his fears in life. Is he afraid of possibly embarrassing himself in front of other people? Or, is he scared of trying new and crazy things? He will most likely use his critical thinking to try and hide his fears.

6 Interesting WYR Questions During A Date

Got a date who is quite a conversant? Do you want to know if you share the same values? Intrigued by his own set of philosophies? Then this list is your friend. Apolitical, straightforward yet thought-provoking, we all love to discover another person’s train of thoughts. From his idea of leadership, food, music to sports - this set of questions can even help you prepare for your future date plans.

Here are 6 interesting would you rather questions:

12. Would you rather start a colony on another planet or be the leader of a country on Earth?

I know we're 100 years away from starting civilization on another planet, but how cool would it be if you had the choice to lead it? It's definitely a lot cooler than ruling the United States or the North Pole. It would be fun to think about what rules you'd want to have, so ask him what proclamations he'd make. Make your date night more interesting when you ask him this weird yet funny question.

13. Would you rather marry the most attractive person you’ve ever met or the best cook you’ve ever met?

When it comes to true love, you really can't help who you fall for. People rarely have these dilemmas because usually, the person you find won't be the most attractive person or the best cook ever. But, if you find the right person, they will be the "most" you will ever need.

14. Would you rather have $1 million now or $5,000 a week for the rest of your life?

Not everyone can be Kim Kardashian, who earns probably more than $5,000 a week. So, let's find out what reasoning he may have for his choice. Practically, getting a large amount of money every week sounds ideal. But, if he's the business-minded type, he'll probably choose the instant million to put up his own business. After all, if you've got a million dollars as your capital, you'll still most likely earn that $5,000 a week.

15. Would you rather listen to music from the ’70s or music from today?

With this question, you'll find out if his favorite famous singer or favorite song comes from a certain period of music. Most people would say they love 70s music, but there is also a lot of new music that is just as good as the songs back then. Either way, you'll know a lot about him when he tells you what kind of music he listens to.

16. Would you rather go deep-sea diving or bungee jumping?

This question would be great to include if you can make a board game out of these scenarios. The current player would choose either one of these options, and they would have different paths to take based on the choice they made. So, if he decided to go deep-sea diving, he might be on a track of water-related questions. If he chooses to go bungee jumping, it will resemble Jurassic Park because of all the crazy adventures to follow.

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

I don't know. Would you rather watch only a corny horror film for the rest of your life or listen to your most hated musical instrument every time you open the radio? Random stuff like this will always be a great idea to start conversations with. It's only a matter of choosing what kind of inconvenience you can deal with.

5 Flirty Questions To Ask A Guy You Like

Suppose you want to know how to flirt with a guy, maybe it's time to think outside of the box and try something new. Using flirty would you rather questions would be a great way to show your interest in the guy you like. Definitely, these flirty questions to ask a guy will help you get the confidence you need to start a conversation with him. Let's dive in!

Here are 5 flirty questions that can help you out:

18. Would you rather date someone you met on social media or someone you met on a dating app?

This would be a good way to know if he is into dating people he hasn't actually met. Either answer will let you know if he's open to something a little risky and adventurous. People can paint themselves in different angles to show the sides they want other people to see. With this question, you'll find out if he's willing to explore that kind of risk.

19. Would you rather date your best friend or someone you don't know?

Each person has a different reasoning for this. Find out if he's the type of person who can take the uncertain risk of changing a successful friendship. Or is he willing to try dating someone he doesn't know? Let's hope for your sake that he would rather date you, though.

20. Would you rather send flowers or receive them?

A normal guy would say that he'd rather send them. But, these days, we see men receiving flowers all over social media. After all, men deserve flowers too. Find out if he's the type of guy who is open to receiving showy gestures of emotion, so you'll know if he's comfortable with getting flowers, should you ever decide to give him some.

21. Would you rather be with someone funny or attractive?

I know people say that looks don't mean as much as personality, but some actually put it at the top of their list. Let's see if this guy is the type who thinks appearances are important. Sometimes, that's not a bad thing. Just as long as he can still appreciate all the other great things about the woman he's dating.

22. Would you rather date a girl who won't stop talking or date a girl who won't stop texting?

Both are the worst, actually. But, see which of these is his real pet peeve. Some people can stand nonstop talking as long as there is substance in the things being said. Some people can withstand continuous texting as long as the person they're with is still attentive. Let's look at how much he can endure.

5 Crazy and Weird Questions For A Memorable Night

Would you rather date someone whose favorite food is hot sauce or stale cookies with spoiled chocolate milk? Now, that's something weird to think about.

There are a lot of crazy and weird scenarios out there that you can present to the guy you're talking to. But, these absurd would you rather questions are perfect for when you want to catch someone off guard. You'd surprise them with your crazy ideas, and you'll find out how they can reason out their choices. If you need a list of crazy and weird would you rather questions, this is just what you need.

Here are 5 crazy and weird questions:

23. Would you rather have a pet dinosaur or a pet dragon?

What's the difference, really? The short answer is fire. Honestly, both would be a pain to have as a pet. They're big, so they've got to eat a lot. Plus, think of all the mess you'd have to clean up after they eat! Of course, there's the added pressure of whether or not they'll eat you, but that's a story for another day.

24. Would you rather get your wisdom teeth pulled or your butt cheeks pierced?

Weird, right? But, if he has already experienced getting his wisdom teeth pulled, he might opt for that since he knows how painful it can be. I mean, if we're speaking from experience, who can we ask about getting piercings on the butt? After all, getting your butt pierced may give your toilet paper another job to do.

25. Would you rather not age or marry a famous actor?

If he's got an intense celebrity crush, he'd probably choose to marry a famous actor. But, if he's a little on the vain side, not aging would probably be the best thing ever. See if he chooses to sustain his youth or spend the rest of his life with his famous long-time crush.

26. Would you rather be trapped in a romantic comedy with your enemies or trapped in a horror movie with your friends?

Now, that's something to think about. Could he withstand his most hated enemies in a sappy, romantic movie? Maybe he could if he gets to drive a nice car and works as a journalist at a magazine. Or, perhaps he'd prefer to be trapped in an old, abandoned mental hospital trying to get out. But, that's probably easier because he'd be with his friends. They would most likely just laugh it off until the morning came.

27. Would you rather be able to time travel within a certain range or be able to freeze time?

Time always runs out, right? But, what if you had the choice to manipulate time? Would you do it? Ask him this question and see if he'd choose to return to a specific time and find out why that was significant to him. You could build on that conversation to find out more about his past.

Downloadable and Printable List Of Would You Rather Questions

Here is a downloadable and printable jpg/pdf list of would you rather questions (right-click the image and select Save As...):

Frequently Asked Questions

Do you have any more concerns about asking would you rather questions? Check out these frequently asked questions and see if they can clear some things up.

Can asking would you rather questions make you know each other well?

Yes. Asking these questions are subtle ways to discover what inconveniences they can endure. You'll find out what things they value and prioritize. Plus, these questions can open up more conversations about their careers, childhood, and friends. You'll definitely learn a lot about each other that way.

What makes would you rather question popular as an icebreaker game?

It's a great icebreaker game because you can ask the most random questions, and they would still be fun and entertaining. Plus, these questions don't need a lot of customizing. You can ask anyone, and they would still be applicable.

Can I play would you rather on zoom?

Yes, you can! You can play this game anytime, even on your senior prom night, if you're feeling a little dull. Playing this on zoom is a great way to virtually bond with your loved ones. You don't need to be physically together to play this game. You just need a handy dandy list that can give you a lot of fun questions to ask your friends.

What are the benefits of asking would you rather questions?

Not only will you have a lot of fun thinking about these crazy scenarios, but you will also learn a lot about people when you ask these questions. It's a great way to bond with your friends and family.

How to Play Would You Rather

If you're looking for a fun way to spice up your bonding nights, use these fun would you rather questions. You will make many new memories playing this game because you'll get to know each other on another level. You'll be reminiscing about this game at your next gatherings.

Here are a few ways to play would you rather:

1. Drink your worries away.

You can play the drinking version of this game if you're looking to get crazy with your friends. To play this, you need at least 3 players. Then, you can use a random picker online to show the would you rather question the players need to answer. When the timer runs out, you will say your answer in unison. The person who picks the least popular option will drink.

2. How well do you know each other?

Let's see how well you know your friends with this version of would you rather. You can use an online app for this. The game will work well with 3 or more players. A current player will choose an answer for a would you rather question. Then, the other players will try to guess the current player's choice. Then, after 10 seconds, the app should show the answer of the current player. Whoever gets the most points at the end of the round wins.

3. Don't get bored with a board game!

There is also a board game version of this game. You don't need to be an Amazon associate to find this board game online. You can now play this game during special occasions when you've got family and friends coming over. Now, your Christmas and New Year's Eve parties won't be as dull once you have this new game to play.

More Questions-Based Games To Discover

Do you need some more question-based games to make more memories with your friends and family? Here are a few more related posts for your next game night:

  1. Everyone needs some ice breakers to ease the tension when meeting for the first time. On our site here, we've got all the best icebreaker games for adults that you need.
  2. There is a great game that you can try when you want to make your bonding moments a little more fun. We've got all the information you need on the Never Have I Ever game on our site here.
  3. If you want to impress a guy, you need to have the confidence to ask serious and important questions. These 21 questions to ask a guy will help you get to know him on another level.

Conclusion

Now, you've got all the information you need about playing Would You Rather.

You now have all the best questions to ask for a Would You Rather game when your friends and family's next gathering. You no longer have to worry about awkward silences and tension-filled moments because we've got all the best conversation starters on our site here. These would you rather questions will definitely break the tension and start wonderful conversations about each other. You'll learn a lot about the people close to you when you ask these questions.

Your gatherings will be more fun and memorable when you play this game. Enjoy!

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