264 Hypothetical Questions: Funny, Hard, Random & for Friends

Thought provoking hypothetical questions

If you could design a planet, what would your perfect planet look like?
Would you want to permanently feel zero pain if given the chance?
How would the world be different if zeppelins had caught on and were the dominant form of air travel?
If you could go back in time and give your parents advice before you were born, what advice would you give them?
If you could erase one thing from existence, even the memory of the thing, what would it be?
If everyone had to post the bad stuff in their life on social media as well as the good, would social media be more or less popular?
If you had an animal or plant renamed in your honor, what would you want to carry your name?
If you could start a secret society, what would be its goals and who would you include?
If you could choose any job to be replaced by robots, what job would you make obsolete?
If you could snap your fingers and make any one species go extinct, which species would you choose?
If you were chosen to be the first human to make contact with aliens, would you want to?
You get one text, no more than 160 characters, it is sent to everyone's phone. What does it say?
What kind of movie or TV show would you make if money and skill weren't an issue?
If you could implant one false memory in the minds of everyone in your country, what would that memory be?
If you could make one legal thing illegal and one illegal thing legal, what would you pick?
If you could merge two games together and make a new one, what games would you choose and what would be the result?
What would you do if you were suddenly given world-class hacking knowledge and ability?
If you had to prove you were human and not an AI in 5 minutes via a text conversation, how would you do it?
If you could go back and uninvent something, what invention would you erase from history?
If you found out you were going to die in a week, what would you do with your remaining time?
If you were tasked with making school more fun, but it still had to be effective at teaching students, what would you change?
If you could make a medicine that would cure one thing, and that thing could be anything, what would your miracle medicine cure be?
If you could be born again in any country, as any race, and as any gender, what would you choose?
If you could design one new animal and bring it into the world, what would it be like?
If you could go back and undo one thing you did, what would you undo?
If androids were a thing, how do you think people would treat them?
If you could get every country and every person in the world to work on one project or goal, what would it be?
If you could redesign the human species, what parts would you add on or take out?
Everyone gets one pardon at birth, good for any crime. What are you saving yours for?
The dead can now testify in court. Which famous case do you reopen first?
Kids can watch footage of their parents at the same age. Which of your parents' rules falls apart first?
Every marriage expires after ten years unless both people secretly vote to renew it. Which couple you know is getting a nasty surprise?
You discover your happiest childhood memory was staged to cover up a family crime. How much of the truth do you want?

Crazy hypothetical questions

What weird thing would you make socially acceptable if you could?
If your sheets had to be made of deli meat, what meat would you want them made of?
If you had to be haunted by a ghost for the rest of your life but could choose which dead person the ghost would be, who would you choose as your ghost?
If you were given the rather lame superpower of being able to make any food you touch go bad, what would you do with that power?
You can transport one furious elephant into any point in history, where would you put it?
If your dog or cat suddenly spoke one sentence and then never spoke again, what would be the most unsettling sentence they could say?
How would our view of space change if the moon was actually made of cheese?
What would be the first few things you would try if you found out you were completely impervious to physical harm?
If you could choose what the next crazy fake health trend was, what health trend would you create?
What cute cartoon character would be absolutely terrifying if it existed in the real world?
What would be great and what would be terrible about all humans having translucent skin and muscles so that you could see all the organs working?
If aliens took over and humans were put into zoos, what would you want in your zoo enclosure?
What would be the cutest non-conventional military unit that would still function as an effective fighting unit?
If all animals became as intelligent as humans and were miraculously able to speak, what jobs would be well suited to which animals?
How would the world change if mammals (including humans) laid eggs instead of giving birth?
If you had a handful of modeling clay and whatever you made would become real until you willed it back into clay, what would you use it for / make?
What would you do with a real bag of holding?
If you had a pen with magical ink inside, what would happen when you wrote something?
If you died and had to choose one place to haunt for the rest of eternity, where would you choose to haunt?
Your severed head can live happily in a bowling bag while your body runs errands. Who do you trust to carry the bag?
Everyone sheds their whole skin once a year. What's the creepiest thing someone could do with yours?
Clouds turn carnivorous. What do you carry instead of an umbrella?
Rain now falls as human teeth. How do you clear your driveway?
You wake up with a ten-foot tongue. How do you get through a job interview?
Everyone hibernates for three months, wherever they fall asleep on December 1. Where are you making sure you nod off?
Every pigeon in town now weighs eighty pounds. How do you protect your lunch?
Your reflection can punch through the mirror. How do you get ready tomorrow morning?

Funny hypothetical questions

Your next hangover arrives in advance, while you're still sober. How much fun would you need to justify it?
You have to fight a mascot on live TV. Which one would you feel least guilty punching?
You can give one person on Earth a wedgie from anywhere, one time only. Who gets it, and at what moment?
Your toilet loudly reviews every flush. What's the worst review it's given you?
A museum wants to display your bedroom exactly as it is. What would the audio guide warn visitors about?
You get a warning label based on how you behaved during your last vacation. What does it say?
Firefighters have to cut you out of something, live on the evening news. What did you get stuck in?
Your stomach gets a lawyer and sues you. Which meal is its strongest evidence?
You're buried with everything currently in your car. What will archaeologists assume you did for a living?
You have to wear a dog cone for a week. How are you explaining it at work?
You must audition for a bank robbery crew. How do you demonstrate that you're intimidating?
Someone hires a skywriter to demand the return of something you borrowed. What's being spelled out above your house?
You get a stunt double for one ordinary task you're embarrassingly bad at. What are they doing?
What two animals would you like to switch the sounds they make?
If you had to do a dance that had never been done in the history of mankind or be killed, what kind of dance would you do?
If you could change the sounds your body makes (i.e., burp, fart, yawn, sneeze, etc.), what new sound effects would replace the normal sounds of your body?
If you could replace any word in common usage with another word and no one would know, which word would you choose?
Would you want to live in a world where everyone's thoughts appeared as text above their head?
If you were obscenely wealthy, what weird eccentricities would you indulge in?
If you could choose a nickname and have people call you it with complete seriousness no matter how ridiculous, what nickname would you want?
If given a chance, would you drink milk from animals we usually don't drink milk from? (i.e., bat milk, cheetah milk, monkey milk, etc.)
If you could put just one word into any document in history, what word would you choose and where would you put it?
If everyone you looked at was compelled to mimic your every move like a puppet, what mischief would you get into?
What would be the most interesting or exciting thing to make a floor in a house out of?
If you were a 90's cartoon evil villain, where would your base be and what would it look like / have inside? What would your henchmen / henchwomen wear as uniforms?
What amusement park do you wish existed?
Your superpower is that you can give phobias to people, what fun and interesting things would you make people afraid of?
If you could change what people say after someone sneezes, what would be the funniest thing for people to say?
If you could rename any five animals, what would you rename and what would their new names be?
If you could choose any mode of transportation, no matter how ridiculous, what method of transportation would you want to use to get around town?
If you could know the internet history of any one individual, who would it be?
If your hands were frozen in one position or gesture, what position would you want them stuck in?

Hard hypothetical questions

Every one of these costs you something, so think before you answer.

If humans lost the ability to see all color except one, which color would you want to survive?
If when you died, you could cease to exist or wander the earth forever never being able to interact with anything, which would you choose?
If you could be invisible, but it would mean being permanently invisible, would you want to be?
If you had to suffer through a massive natural disaster but could choose which disaster to face, which would you choose?
If you could know when and how someone would die just by shaking their hands but couldn't change their fate, how would you use that power?
Would you choose to know your future if it meant forgetting your past?
If you could level up any aspect of yourself (i.e., strength, intelligence, charisma, etc.) but you had to decrease another aspect of yourself by the same amount, what aspects would you increase, and which would you decrease?
What would you do if a teaspoon of your tears could be used to cure cancer in one person?
If Jedi were real, but you had to give up all your possessions and never have a romantic relationship, would you still become a Jedi?
Would you choose to become more intelligent if it meant you were generally unhappier?
Would you sign up to be a colonist on another planet if it meant you would never be able to return to earth?
Would you add 100 years to the end of your life if you spent all of them old and frail?
You can buy one more year with someone you've lost. Each year costs everything you earn that year. How many years do you buy?
Everyone you love will live to ninety if you never touch another person again. Who would be hardest to explain that to?
Every month you spend in solitary confinement pays $100,000. Quit early and you lose all of it. How many months do you sign up for?
You can cure every illness you'll ever have, but every night you'll dream you're being eaten alive. Would you take it?
You can guarantee your child a happy life, but only if you disappear from it completely. Do you go?
Someone will pay off every debt you have, but your worst secret goes on a billboard in your hometown. Do you take the deal?
You can become completely fearless, but you'll never feel guilt again. Who should be worried?
Your dream body comes with a catch: everything tastes like unseasoned oatmeal forever. Would you go for it?
You become the world's best surgeon, but your hands shake whenever you're not operating. Would you accept?
Your entire family gets $1 million if you let them vote on who you marry. How much do you trust that committee?
A billionaire offers you $5 million to control your life for a year. What's the one rule you'd put in the contract? Anything else legal is fair game.
You get your dream home for free, but a ghost screams in it for an hour every night. Only you can hear it. How long do you last?
Every health problem you have is cured, but you wake up with a stranger's face for good. Do you take it?
Hospitals can transfer a patient's pain to a willing visitor for an hour. Whose pain would you take?

Hypothetical questions to ask your friends

Ask these when the whole group is together. Most of them are about who would do what.

Our lottery pool wins, but one person forgot to pay their dollar. How much are we giving them?
You hear that everyone else here got arrested together. What do you assume happened?
We're in a horror movie. Whose dumb decision gets the first one of us killed?
A demon will leave us alone if someone tells a convincing lie. Who do we push forward?
One of us starts a cult. Who joins for the free snacks and ends up second in command?
We're stranded in medieval times. Who gets accused of witchcraft first, and what stupid thing did they do?
We're robbing a casino and someone has to distract security for ten minutes. Who goes, and what scene do they make?
We take over a country. What scandal brings down our government before the first weekend?
A stranger insults one of us in a bar. Who makes things worse while trying to help?
You have to argue your way out of hell, and you get one lawyer from this group. Who do you pick?
We're contestants on a reality show. Which two people secretly form an alliance, and who do they throw under the bus first?
What would be your strategy for a zombie apocalypse?
If you could be the CEO of any company, what company would you choose?
If money wasn't a concern where would you live, what would you do, and what would your lifestyle look like?
If you could move anywhere and still have a livable wage, where would you like to move?
If you could get a ticket to any show or event, what would you want a ticket to?
If you were head of product development at a major fast food chain, what food abomination would you create?
If you worked in the entertainment industry and had a pseudonym, what would your alias be?
If you could create any one reality TV show, and it was guaranteed to air, what show would you want to put on TV?
If you could be a top tier professional athlete in any sport, what sport would you play and why?
If someone offered you $10,000 every time they punched you in the face, how many times would you want to be hit?
What movie worthy heist would you pull if you knew, in the end, you would get away with it?
If someone created a bar or cafe with just your tastes in mind, what would it look like?
Would you dance for two minutes with no music in front of a packed stadium for $50,000? What kind of dancing would you do?
If you could call yourself when you were fifteen years old for a twenty-minute conversation, what would you tell yourself?
What sport would you like to compete in professionally if you had the ability and skill to?
If you had to join the circus, what type of performer would you be?
What kind of business would you like to start if you were given a chance?
If you could control your dreams, what would you dream about?
If you could deck out one room in your house in any way you'd like, which room would you choose and what would you do to it?
If you won the lottery, what would NOT change?
If you launched your own drink brand, what would it be, what would you call it and what would make it different?
If you could be fluent in four languages, which languages would you choose?
If you could go back and hands down win any argument you've had with anyone, what argument would you choose to win?
You can choose anyone in the world to become friends with, who would you choose?

Random hypothetical questions

If extra lives were a thing in the real world, how would you get them?
What animal would be way better if it was covered in scales?
What do you wish grew on trees?
If every time you snapped your fingers, you would instantly be transported to a random point in humanity's timeline, would you snap your fingers? If so, how often?
If you could put wings on any species of animal, what animal would you choose?
If you were forced into gladiatorial combat, but could only choose a weapon that isn't typically considered a weapon, what non-conventional weapon would you choose?
If you had to get a tail, what tail would you want and what would you use it for?
If someone left you a castle in their will, where in the world would you want it to be?
How would the world change if there was no internal monologue and everything you thought, you spoke out loud?
Would you want a house where every wall was made of giant TVs if you could choose the channels but never turn them off?
If you were given any one luxury item, but you couldn't sell it, what luxury item would you want?
If you could choose one element to control, what element would you choose?
Would you take a weekend job for 20k a year to be a human scarecrow and chase birds from fields?
What shape would you want your house to be if it could be any shape and still function?
What animal would be the cutest if it was the size of a chihuahua?
If you were on death row but could choose any way to be executed as long as you died within a couple of days, how would you want to die?
If hide and seek were a major sport in the Olympics, what would it be like?
What fantasy creature would you love to bring into the real world?
If you could afford a live-in butler or maid, would you want one?
If you could harmoniously unite two countries into one, what two countries would you choose?
If you could make any non-edible thing edible to humans, what would you choose?
If you could control one part of your body that normally runs on its own, like your heart rate or body temperature, which would you pick?
If you could become three times bigger or fifty times smaller whenever you wanted, which would you spend more time as?
If you could choose any vehicle to drive around for a couple of hours, which vehicle would you choose?
If you could be an NPC in any videogame, what game would you choose to reside in?
Every day 12 things appear in your backyard, they are random, but all start with a letter of your choosing. What letter do you choose?
If you had to eat the same breakfast, lunch and dinner every day, all three different, what would they be?
If you could body swap with any person for 24 hours, who would you choose?
If you could put a new word in the dictionary, what would it be and what would be the definition?
If you could bring back any canceled TV series, which TV show would you choose to bring back?
You get $500 for letting a police dog tackle you in a padded suit. How many rounds are you booking?
Your dentist offers free care for life if you let them give you vampire fangs. Do you sign?
A car wash offers to clean you for free on its gentlest setting. Are you going through the car wash?
A movie needs a close-up of someone chewing a live worm. How much for one take?
Everyone gets one legally binding "mind your own business" a year. Who gets yours?
A proposal at work to shorten meetings, every meeting must happen while everyone holds a squat. Would you vote for or against the proposal?
People must personally deliver every one-star review. Which business would you still march into and give your one star face to face?
Everyone's front door displays the number of cockroaches currently inside. What number makes you cancel a visit?

Interesting hypothetical questions

What laws would you abolish if you could? What laws would you create?
What cartoon world do you wish you could live in for a week?
If you were perpetually surrounded by one aroma (besides your natural smell) which you and everyone around you could smell, what would it be?
If everyone was mentally incapable of lying, how would that change the world?
If you were required by law to get a full body tattoo, what would you get tattooed over your entire body?
If you were reincarnated as an animal based on your personality, what animal do you think you would come back as?
What futuristic thing from a sci-fi movie or book do you really wish existed right now?
What two-hour chunk of history would you want a video of if you could have video of any point in history?
If you started an activist group, what would it fight for and what would it be called?
How would you change how you acted if you knew 100% that the world was a simulation?
What would you do if you had your own intergalactic space ship roughly the size of a house?
If you were tasked with redesigning your country's flag, how would you change it?
Be honest: if you were born in medieval times, you probably wouldn't be royalty or a knight. So what kind of peasant would you be?
If your life was made into a movie which actor would play you?
If you had a symbol or crest that represented you, what would it look like?
If you could live under any form of government, which would you choose? Skip this one if anyone in the group has strong political views.
If you could accomplish simple tasks while sleeping and still get a good night's sleep, what would you want your body to do while you were sleeping?
If you had an endless supply of LEGOs but couldn't sell them, what would you build?
If you could make one thing taste like another, what would it be?
Assuming you don't get seasick, what would your dream sailboat or boat look like and what would you name it?
What sound do you think you would miss most if you went deaf?
If you were able to throw a party and money wasn't an issue, what kind of party would you throw?
When would you be born if you could choose to be born at another time?
If you could design a new holiday, what holiday would you create and what traditions would it have?
If you could live inside someone else's head for fifteen minutes, whose would you pick?
If you could ask anyone in history three questions and you'd understand each other perfectly, who would you ask and what?
If you could know the truth behind any one secret or mystery, what would it be?
Wedding vows become physically impossible to break. Which sentence are you checking before you say it?
Presidents are picked like jurors, and your name comes up. How would you try to get dismissed?
Blocking someone online also makes you invisible to them in person. How would that change the world?
Retirement begins whenever you choose, but going back to paid work is illegal. At what age would you risk it?
On your birthday, you can legally invoice one person for wasting your time that year. Who gets the bill?

“If you were a…” hypothetical questions

Quick ones about who you'd be if you weren't you. Some are silly and some get a little dark.

If you were a transformer, what vehicle would you turn into?
If you were a food, what food would you be?
If you were a professional wrestler, what would your name and entrance be?
If you were a superhero or villain but could only have powers nobody has had before, what would your powers and name be?
If you were the king of an ancient civilization what would you want your tomb to look like?
If you were a dictator of a small country, what crazy dictator things would you do?
If you were a fashion icon and whatever you wore would become a fashion trend, what fashion trends would you start?
If you were the next pied piper, what animal would you want to be able to compel to follow you?
If you were a genie, how would you ruin someone's wish to be the most attractive person alive?
If you were a demon possessing someone, what habit of theirs would make you demand an exorcism?
If you were an alien lawyer trying to get Earth demolished, what TV show would you play for the jury?
If you were a cursed doll at a garage sale, how would you persuade someone to buy you after they saw you move?
If you were a vampire, what would someone have to say halfway through dinner for you to stop drinking their blood?
If you were a pirate captain, what petty offense would you make someone walk the plank for?
If you were a cursed sword, what would your owner have to shout every time they swung you?
If you were a mosquito with one bite left, who would you use it on, and where?

“What would you do?” hypothetical questions

Real-life moments with no easy way out. Answer with what you'd really do.

You accidentally like an ex's wedding photo from four years ago. They immediately message, "Everything okay?" What's your reply?
Your friend uses you as an alibi without asking. Their partner wants to know what you did together last night. What do you say?
A friend's apology text was clearly pasted from AI, including "make them feel guilty for overreacting." What do you send back?
A coworker gets fired for leaking a screenshot you sent them. Nobody suspects you. How far do you let this go?
A customer leaves you a $500 tip, then returns crying because they meant $5. You've already spent half. What do you tell them?
Your boss accidentally sends you everyone's salaries. You're paid least, and they immediately ask you to delete the file. How do you reply?
You overhear friends planning a trip they told you was canceled. They haven't noticed you. How do you make your entrance?
You receive a voice message from a friend trashing you, followed by "Wrong person." How do you respond?
A friend selling homemade cakes wants a five-star review. You watched them pick a cockroach out of the batter. Do you write it?
At a funeral, someone asks you to confirm a flattering story about the deceased that you know is completely false. What do you say?
Your boss tells an offensive joke at dinner, then asks why you're the only person not laughing. What do you say?
Your boss praises your work, then announces you'll teach the AI system replacing you. What do you say in the meeting?
You discover the expensive gift your friend gave you was stolen from another friend. Both are coming over tonight. What happens next?
Your sibling brings your childhood bully to dinner and announces they're engaged. How much of the past comes up over dessert?
You accidentally clog the toilet at a house showing. The agent is leading another couple upstairs. What's your move?
Your delivery driver asks you to say the food never arrived so you can split the refund. What do you tell them?
You hear a party guest telling your most embarrassing story as if it happened to them. Do you claim it?
Your friend's kid breaks your TV, and your friend says you should've bought a sturdier one. What's your next sentence?
If your salary was doubled, what would you do with the extra income?

Hypothetical questions for couples

Good for a date night or a long drive. If you want more, try our questions for couples.

At our wedding, everyone we've ever dated gets two uninterrupted minutes at the microphone. Whose turn are you most worried about?
We're 80 and get permanently banned from a casino. What did each of us do?
Your partner joins a cult and seems happier than ever. How long before you go along to see what the fuss is about?
Every apology you give your partner has been tattooed on you. How much skin have you got left?
You die first and your partner hires a psychic to contact you. What would you say to prove it's really you?
Your partner's diary from 2050 arrives in the mail. Would you read it before giving it to them? And if so what would you be looking for?

PDF of our hypothetical questions

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264 Hypothetical Questions

Hypothetical questions list