99 Hard Would You Rather Questions – The Ultimate List

Entertainment By James 

99 Hard Would You Rather Questions – The Ultimate List

Entertainment By James 
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Whether you’re trying to break the ice with a new group of people or simply beat boredom with an old group of friends, there’s nothing wrong with a round of “Would You Rather.” It’s a game that everyone should already know and that everyone can play. Well, at least anyone with the guts to be honest and occasionally a little gross can play. Rather than think up some on your own, we’ve done the legwork for you. Here it is, the ultimate list of hard Would You Rather questions that are fun and tough.

Table Of Contents


  • Big Decisions
  • Life Altering
  • Historic Hypotheticals
  • Getting Personal
  • Let’s Talk Anatomy
  • For Entertainment Purposes


Big Decisions (18)


  1. Would you rather sleep with your boss for a promotion or get fired?

There are a lot of people who have slept their way to the top, but what if your only other choice was to lose your job entirely? How are your morals and ethics when there’s no middle ground?


  1. Would you rather have loud neighbors or nosy neighbors?

Perhaps you’re the noisy one on the block or in your building, which would make this a rather easy question. However, don’t discount how annoying it is to have neighbors who are always up in your personal business. That’s why you have parents, right?


  1. Would you rather your first child born when you’re 16 or when you’re 46?

Nobody really sets out with the goal of being a teenage parent? But keep in mind that if you have kids early, you can get them out of the house while you’re still young enough to return to your life. If you have a kid too late, good luck with that, grandpa.


  1. Would you rather be a 3rd-string quarterback in the NFL or the best cricket player alive?

There may be no job on the planet that pays better for doing nothing than 3rd-string quarterback in the NFL. It’s good work if you can get it. But don’t you want to be the best, even if it’s at a sport nobody cares about in the Western Hemisphere.


  1. Would you rather master every musical instrument or every language?

It’s tough to go wrong here. Think of the women you could pick up or the trouble you could cause by knowing every language. Then again, think of the beautiful music you could make.

  1. Would you rather know the truth about UFOs or the truth about Bigfoot?

This comes down to your personal preference and which option fascinates you the most. But if you think about it, there’s probably a better chance we get to the bottom of Bigfoot in our lifetime than the government admitting that UFOs are real.


  1. Would you rather work 60 hours per week and be rich or work 10 hours per week and make enough to get by?

Some people want to be rich at any cost. But just think about everything you could do with all of your free time, even without much disposable income. I mean, the number of shows you could binge, right?


  1. Would you rather wear a tuxedo everywhere you went or be forced to wear a diaper under all of your clothes?

A diaper you could possibly hide, although people are bound to find out sooner or later. The tuxedo is the safer option, but do you really want the hassle of wearing that your entire life?


  1. Would you rather give up meat or alcohol for the rest of your life?

You guys are on your own with this one. Just flip a coin because this one’s impossible.


  1. Would you rather fart loudly while giving an important presentation or have a smelly fart while alone in a sealed room?

This one all comes down to self-preservation. Do you take the bullet for yourself or assume your career can survive one foul (smelling) moment?


  1. Would you rather spend your life alone on a private island or alone in a mansion?

Either way, you’re gonna be on your own forever. Do you wanna sit back in the sun eating coconuts or have a fridge full of food and comfortable couches?


  1. Would you rather have free food at any restaurant the rest of your life or free air travel the rest of your life?

There’s probably some leg work here on what option is the smart move financially, although my inclination is that you’ll ironically get further by taking the free food. Plus, you’ll never have to cook again, so there’s that.


  1. Would you rather live in a world in which the clouds always cover the sun during the day or a world in which the clouds cover the moon and stars at night?

This kind of depends on whether you grew up in a sunny place. Also, if you’re a bit of a dreamer, you’ll probably take the stars, and I don’t blame you.


  1. Would you rather live in a big house with all glass walls or live in a tiny studio apartment that’s underground?

If you take the big house, keep in mind you won’t be able to throw stones. Also, privacy could be an issue, although it’s nice to have plenty of space.


  1. Would you rather burn down a one-family home or an entire forest full of animals?

You may claim that you love animals, but we’re about to find out just how much?


  1. Would you rather be part of a food fight that never ends or a water balloon fight that never ends?

Once again, there’s no bad option here. It does seem a little wasteful to throw all of that food away. On the other hand, a non-stop water balloon fight probably means you’ll never feel what it’s like to be dry ever again.


  1. Would you rather have a maid who only cleaned your bathroom or only cleaned your kitchen?

Kitchens are usually bigger and take longer to clean. However, bathrooms are known to be icky, so this one’s tough.


  1. Would you rather show up to work every day without pants on or without a shirt?

Where exactly does your shame lie? If you’re wondering, yes, you’d be wearing underwear of some kind, but that doesn’t make it much better.



Life Altering Choices (22)


  1. Would you rather go back in time to witness history or go forward to see the future?

Honestly, this question reveals a lot about you as a person. Are you the type to dwell on the past or look ahead to the future?


  1. Would you rather win $100 million in the lottery or extend your life by 50 years without aging?

That’s a lot of money to turn down. You may love your life and want to extend it as much as possible, and that’s fine. I’m just saying that’s a whole lotta cash.


  1. Would you rather live in permanent winter or permanent summer?

This kind of boils down to how much you like skiing, building snow forts, and it “feeling like Christmas” in December. If you can get by without that, this should be an easy choice.


  1. Would you rather give up pizza or give up ice cream for the rest of your life?

Think about it this way, there are a lot of ways to indulge your sweet tooth. Are there any foods out there comparable to pizza?

  1. Would you rather lose your hearing or your sense of taste?

The good news here is that you aren’t going blind. But people underestimate how great it is to taste stuff, so this one is tough.


  1. Would you rather be able to see ghosts or die and come back as a ghost?

Are you haunted or do you want to do the haunting? I mean, doing the haunting sounds way more fun, but technically, that option involves leaving this dimension, so there’s that.

  1. Would you rather give up social media or give up being able to taste your food?

Is posting every food dish on Instagram really worth not being able to taste that food anymore? Yeah, it just got real.


  1. Would you rather know when you’re going to die ahead of time or know how you’ll die?

If you know how, maybe you can put death off. Then again, if it’s something gruesome, maybe you don’t want to know how it’s coming.


  1. Would you rather be able to read other people’s minds or control other people’s actions?

This one is all about how much of a control freak you are. Reading minds sounds fun, but some people just feel the need to control everything, don’t they?


  1. Would you rather have perfect health but be homeless or have all the money you need but constantly battling illnesses?

If you’ve ever been seriously ill, you should know that you’re nothing without your health. Then again, with enough money, staying in bed all day might not be that bad.


  1. Would you rather have to watch the animal you’re about to eat die every time you eat meat or only eat fruits and vegetables that you have to grow and pick yourself?

Nothing comes easy here. You’re either flooded with guilt or sentenced to a life of picking berries and tending to your garden.


  1. Would you rather grow up poor and become rich late in life or come from money but go broke as an adult?

Please pick the latter; I love the idea of trust-fund kids losing everything and ending up on the streets. Too mean?


  1. Would you rather be a world-class author or have a perfect memory?

Having a perfect memory is a good way to trick people into thinking you’re smart. Of course, brilliant writers don’t grow on trees either.


  1. Would you rather be a human lie detector or be able to get away with lying?

Here’s another one that’s all about control. If you can get away with lying, you can get away with a lot. On the other hand, it’d be nice to call people out on their crap, right?


  1. Would you rather spend the rest of your life without a working toilet or a working refrigerator?

Something big is about to change, either going in or going out. In the end, this choice comes down to taste vs comfort.


  1. Would you rather get $1 million today or get $40 million in 40 years?

Forty years is a long time to wait, but that’s a massive payout and generational money. However, if you’re smart, you can make $1 million go a long way without having to work.

  1. Would you rather colonize a new planet or discover an uninhabited island?

It’s tough to go wrong with your own island, even if you’re starting from scratch. But think of how many islands you could own if you’re the first to colonize a new planet.


  1. Would you rather become an all-powerful dictator or the richest person in the world?

Someone famous once (allegedly) said: “Give me control of a nation’s money and I care not who makes its laws.” Do you feel the same way?


  1. Would you rather spend five years in a maximum security prison and then be released or spend 40 years in a minimum-security prison?

For some people, being in a minimum-security prison means having kind of a cushy life, but it’s not the same as freedom is it?


  1. Would you rather testify against a close friend or family member or go to jail for a crime they committed?

Do you fancy yourself as a loyal person? Just how far does that loyalty go?


  1. Would you rather only eat food from a gas station or only use gas station bathrooms for the rest of your life?

This is a tricky one because if all of your meals are eaten at a gas station, you may not have time to get home before having to use the bathroom.


  1. Would you rather live forever in your hometown or live the rest of your life somewhere else that’s been randomly selected?

This is really more about how comfortable you are at home and how adventurous you are. In theory, you could be randomly selected to live in Paris or Honolulu, but you could also get some tiny town in Idaho no one’s heard of before.



Historic Hypotheticals (11)


  1. Would you rather be a passenger on the Titanic or the Hindenburg?

If you don’t already know, there were survivors for both of these tragedies. It just comes down to whether you think you’d be better off surviving a giant fireball or the icy Atlantic.


  1. Would you rather fight and be on the losing side of the Civil War or World War II?

As we know, things didn’t go well for the losing side in both of these wars, although the North was a little more forgiving than the Allies were.


  1. Would you rather live through the Great Depression or the Bubonic Plague?

If you could find a way to eat, you’d probably survive the Depression a little easier than the Plague? But it wouldn’t be easy, so maybe take a chance on your body’s immune system.

  1. Would you rather live without the music of the 1960s or the music of the 1990s?

Let’s be honest, both of these decades had some incredible music, but you can only keep one in the lexicon of music history.


  1. Would you rather be an evil dictator who can’t be stopped or lead a democracy that defeats an evil dictator?

This one really just boils down to whether you’d prefer to be a hero or a villain. Most people would say hero, but what’s the harm in being a villain if no one can ever stop you?

  1. Would you rather go on Louis and Clarke’s journey or Paul Revere’s ride?

This is simple: do you want to be famous for one night’s work or spend years being one of the first people to set foot on a new territory?


  1. Would you rather invent Facebook without getting credit or money for it or paint Starry Night without getting credit or money for it?

Either way, you’re getting nothing out of it, but what would make you more satisfied as you live in anonymity?


  1. Would you rather oversee a concentration camp during World War II or oversee a plantation before slavery ended?

Is there a lesser of two evils in this scenario? Probably not, but that’s why the game is called “Would you rather.”


  1. Would you rather know the truth about the Bermuda Triangle or Stonehenge?

Where exactly does your curiosity lay? I guess we don’t know for sure if something is up with the Bermuda Triangle, but if there is, wouldn’t you want to know?


  1. Would you rather have lived the life of William Shakespeare or Pablo Picasso?

Picasso lived a little more recently if that matters. However, Shakespeare’s work and name have stood the test of several centuries. That’s got to be worth something, right?


  1. Would you rather go back in time to prevent the assassination of Abraham Lincoln or John F. Kennedy?

For what it’s worth, Lincoln had already done his part to change history whereas Kennedy hadn’t even served a full term. On the other hand, only Lincoln is on Mount Rushmore.



Getting Personal (16)


  1. Would you rather marry your dream girl/guy but for only five years or have a 40-year marriage with someone else?

Do you want to find true love or do you want a nice life? Unfortunately, those two things can be mutually exclusive.


  1. Would you rather be rich and lonely or marry your favorite celebrity and be poor?

Fame and money often go together, but not in this case; you only get to pick one.


  1. Would you rather the love of your life live 5,000 miles away or live next door but with someone else?

Would you really be down with your ideal partner being married to someone else and pining for them from next door? If it’s better, you have the option of them being out of sight and out of mind.


  1. Would you rather get a one-night stand pregnant (or be impregnated by a one-night stand) or get an STD that has no cure?

Okay, so this question is probably a little different for men and women, but let’s assume that if you’re a guy, you wouldn’t abandon the pregnant girl. Makes it a tough choice, huh?


  1. Would you rather have a sexless marriage with a supermodel or have sex every day an average-looking partner?

Even a sexless marriage with a supermodel must have some perks, right? But is it enough?


  1. Would you rather go bald or have both your nose and ears double in size?

In theory, being bald is a lot more common and acceptable. But how much do you value that pretty head of hair?


  1. Would you rather nobody touch you for the rest of your life or be incredibly ticklish any time anyone touched you?

Seriously, where do we come up with this stuff? Imagine trying to get down with your partner and every time he or she touches you, all you feel is a tickle.

  1. Would you rather have your wedding vows be all Star Wars quotes or Nickelback lyrics?

Keep in mind all of your friends and family will be there. Are there enough romantic moments in Star Wars to get by or will you have to settle for the dreaded Nickelback?


  1. Would you rather ditch all of your friends for the love of your life or keep your friends and be single forever?

How far are you willing to go for love? Also, what do you value more, love or friendship?


  1. Would you rather give up Instagram or give up Facebook for the rest of your life?

Come on, this isn’t that bad, right? You’ll still have one of these social media sites, but having both is out of the question.


  1. Would you rather have a good looking partner who ignores you or a less attractive partner who showers you with love and attention?

Sorry about this one, but we need to get to the bottom of just how superficial you really are. Exactly what are you willing to give up for a pretty face?


  1. Would you rather pay alimony to 10 different ex-spouses or stay single forever?

First, you have to ask yourself: “Can I afford to pay alimony to 10 different people?” If not, looks like you’ll be single forever, buddy?

  1. Would you rather your partner offer to participate in a Ménage à trois or have a random couple ask you to be the third person in their Ménage à trois?

If memory serves, the gals on Sex and the City had an episode about this. Obviously, a Ménage à trois with your loved one is a great fantasy, but it can also be flattering to be asked to join one. Plus, the latter option isn’t going to get messy, at least not for you.


  1. Would you rather never attend another party for the rest of your life or be forced to serve as the host of every party to attend?

It’s really such a hassle having to host a party. Do you ever get to enjoy yourself? Well, what if that was your only option? The only good part is that you’d never have to drive home after another party, so that’s something.


  1. Would you rather have your secret diary published online or make a sex tape that gets leaked?

Either way, your privacy is going to be violated in a serious way. It’s just a matter of whether it’s your body or your mind.


  1. Would you rather have no one show up to your wedding or no one show up to your funeral?

If it’s your funeral, at least you won’t be there to notice that nobody has bothered to show up, so why would you care? But at least if no one’s there at your wedding, you still have time to make amends before your funeral.



Let’s Talk Anatomy (13)


  1. Would you rather be 7 feet tall or 4 feet tall?

There are obvious disadvantages to both of these options, although if you’re 7 feet tall, it’s a lot easier to turn that into a fruitful basketball career. However, people that tall don’t always live as long, so there’s a little trade-off.


  1. Would you rather only show signs of aging from the neck down or above the neck?

Well, if you only age from the neck down, it’ll be a lot easier to hide from the rest of the world. However, as we all find out at some point, aging can be painful in more ways than one. On the other hand, your face may age like everyone else, but you could dominate the tennis league at your retirement community.


  1. Would you rather bite your tongue 10 times a day or get 10 paper cuts every day?

Wow, how bad are you at eating if you bite your tongue 10 times a day? Of course, paper cuts aren’t much fun either, so you’re going to be in some pain either way.


  1. Would you rather have short legs and crazy long arms or super long legs and super short arms?

Just take a minute to think about how funny both of these scenarios will make you look. Both are going to look silly, so you might as well pick the one that works for you. Long legs would definitely make you taller, but you could do a lot of with crazy long arms.


  1. Would you rather have the long tongue of a snake or the long tail of a monkey?

Okay, right off the bat you should understand that both of these options are going to freak people out. But there are advantages to both. The tongue of a snake is akin to enhancing a few of your senses. But think of the balance and leaping ability you would have with a monkey’s tail.


  1. Would you rather have a uni-brow for the rest of your life or lose your two front teeth and not be able to replace them?

This is definitely a no-win scenario no matter who you are. From a superficial standpoint, people will assume there’s either a funny or sad story behind your missing teeth whereas a unibrow just makes you look too stupid or lazy to fix it.


  1. Would you rather have the long trunk of an elephant or the long neck of a giraffe?

Even if you’re not worried about lions on the savannah coming after you, there have to be some benefits of having a giraffe’s neck and being able to see long distances. Then again, an elephant’s trunk can do some crazy things. They may not be super useful things, but they’d be fun.


  1. Would you rather sound like Gilbert Gottfried or Fran Drescher for the rest of your life?

If you don’t know who both of these people are, Google at your own risk. When you do, you’ll realize that there’s no easy answer to this one. Either way, you might as well just learn sign language and communicate that way the rest of your life.


  1. Would you rather go through life barefoot or be forced to wear socks on your hands?

Going barefoot doesn’t sound too bad, but it’ll depend a lot on where you live. Of course, there are some obvious limitations to living with socks on your hands, even if it does look amusing.


  1. Would you rather never gain weight no matter what you eat or show no signs of aging?

If you’re vain, this question is right up your alley. Think about it this way, everybody is going to age, but eating anything without gaining a pound is going to save you a lot of time at the gym and a lot of time counting calories.


  1. Would you rather have the hiccups non-stop or a runny nose that never went away?

Even I’ll admit that this one’s a little sick (pun intended). Let’s be honest, there are few things more annoying in life than having the hiccups. Even a minute or two of it feels unbearable. On the other hand, no one’s going to go near you when your nose is running for fear of getting sick themselves, so this isn’t an easy choice.


  1. Would you rather have one of your feet chopped off or one of your hands chopped off?

This question really comes down to how good you are at getting around on crutches and how much you like playing sports outside of bowling. Then again, you won’t be playing many sports with one hand either. Also, what hand will be cut off could sway your choice, although that’s less of a concern for ambidextrous folks.


  1. Would you rather have a second belly button or only one nipple?

Either way, you have a bright future being part of the freak show attraction with a traveling circus. The choice probably comes down to what option will be easier to explain to other people without freaking them out too much.



For Entertainment Purposes (11)

  1. Would you rather only be able to listen to jazz or heavy metal for the rest of your life?

Jazz can be nice, but it’s not for everyone. Of course, the same can be said for heavy metal. Unfortunately, you have to pick one and live with it forever.


  1. Would you rather only watch movies for the rest of your life or only watch TV shows?

Okay, so this isn’t the worst thing that’s ever going to happen to you. But just imagine your Netflix options being cut in half. We all have favorites that we’ll never be able to watch again, so the choice isn’t easy.


  1. Would you rather watch every movie without sound or have every movie you watch cut out midway through?

In theory, you’d still be able to watch with subtitles on, so you’d know what’s going on. But you still wouldn’t get the full movie experience. Of course, the same can be said of only being able to watch the first half of a movie. You’d figure that would be endlessly frustrating, although most movies you can probably guess the ending by the midway point.


  1. Would you rather be Cinderella or Belle from Beauty and the Beast?

Obviously, both get a happy ending, although the path to get there is awfully different. If you’re Cinderella, you’ll have to worry about your evil step-sisters coming back for revenge, but if you’re Belle, you have to live your life knowing that all of your friends used to be animated teapots or clocks, so that might be a little weird.

  1. Would you rather be Luke Skywalker or Han Solo?

Okay, let’s forget about the sequels and just focus on Episodes 4, 5, and 6. Luke is obviously the hero and has unlimited access to a lightsaber. On the other hand, Han is a rebel, a renegade, and a bit of a ladies man. Those are definitely qualities to be valued, which makes this a tough choice.


  1. Would you rather be Timon or Pumba from The Lion King?

There’s no wrong choice here because both are lovable characters. Timon, of course, is a lot smarter and a born leader, but he’s also a little high strung. If you pick Pumba, you’re a lot more relaxed and in control of your emotions, but you’re also a little slow and have some intestinal issues that could hold you back.


  1. Would you rather be forced to teach nuclear physics to Lindsay Lohan or have Jessica Simpson try to explain to you the difference between chicken and tuna?

Both of these activities sound excruciating to live through. It kind of comes down to whether you’d prefer to be the student or the teacher. Of course, if you have a preference between the two ladies named, that’ll make the decision easier too. But if all other things are equal, it’s a lot easier to tune out if you’re listening rather than speaking.


  1. Would you rather be part of the cast of Friends or part of the cast of Saved By the Bell?

Surely, you like at least one of these shows, so this shouldn’t be too difficult of a choice. Of course, the major difference is that the Saved By the Bell gang is in high school while the Friends crew is a little older. But even if you’re not in high school anymore, who can say no to hanging out with Zack Morris or trying to get a date with Kelly Kapowski?


  1. Would you rather have Taylor Swift call you out in a revenge song or get into a physical fight with Nicki Minaj?

Miss Swift has practically made a career out of writing embarrassing songs about ex-boyfriends, so it can’t feel too good to have her call you out publicly. Then again, a fistfight with Nicki Minaj is no cup of tea and it might not be better than a war of words with a pop star.

  1. Would you rather never go on another date or only date via reality television shows?

Okay, please don’t tell me you’re one of those people that actually want to go on reality dating shows. Spoiler alert, you’re never going to meet “the one” by going on those shows. On the other hand, you’ll never meet anyone if you can’t date again. Still, it seems painfully frustrating to be constantly going on reality shows.

  1. Would you rather your life be more like Grand Theft Auto or more like Super Mario Brothers?

Okay, so most of us have probably had fantasies about living out a Grand Theft Auto fantasy. But a life of going to strange lands and trying to rescue a princess sounds appealing too. Also, mushrooms and turtles aren’t going to kill whereas being a criminal could catch up to you sooner than you think.