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126 Hypothetical Questions That Will Make Your Conversations More Interesting

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Passionate about words and a purveyor of beard balms. At peace when traveling and songwriting. At comfort sipping gin in my favorite leather jacket. Keep up with me on Twitter @TheNealSawyer Read full bio.

Last Updated: Mar 13, 2024
26 min read
Hypothetical Questions Young Couple Deep in Thought While Lying on Floor

Do you often find yourself stuck in dead-end, monotonous conversations?

It may be because you’re relying too much on small talk.

Expanding your dialogue has many benefits, from breaking the ice on a date to building stronger connections with your friends.

Hypothetical questions are an excellent way for you to ignite the flame of conversation. And in this article, I’m going to unleash a boatload of them onto you.

Gents, your excuse for not having anything interesting to say is about to evaporate.

What Is a Hypothetical Question?

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A hypothetical question is a question based on fiction rather than facts. We design them to elicit opinions and spark conversation.

No subject is off-limits—topics typically range from the philosophical to the downright crazy.

21 Best Hypothetical Questions That Will Spark Fun Conversations

These are my picks of the best hypothetical questions to get you started. 

They’re your reliable go-tos worth memorizing to level up your conversations.

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Which five famous people, living or dead, would you want at your imaginary dinner party?

drunk marilyn monroe GIF by hoppip

Possibly the most common hypothetical question and a sure-fire hit to get the cogs turning.

You could enjoy an apéritif with Jim Morrison, cake with Marylin Monroe, or an after-dinner cigar with Winston Churchill.

Let your imagination run wild and revel in others’ deep thought process. 

Bonus points included for contemplating how your guests would interact with each other. You ever wondered how Fidel Castro and JFK would get on sitting opposite each other?

You’ve sold your soul to the devil, what did you sell it for?

The tale of Faust is perhaps one of the first notable cases of this fabled idea. Faust, a German theologist, disillusioned with life, makes a deal with the devil in return for knowledge and power.

The tale of aspiring blues musician Robert Johnson might be the most epic.

Upon heeding the advice of an unknown music legend, he took his guitar to the crossroads to sell his soul. Here he supposedly met the devil who tuned his guitar. Ever since that fateful night, Johnson was a master of his instrument.

He would influence some of the most influential bluesmen in history until his death at the age of 27. His music inspired music greats including the Rolling Stones and Led Zeppelin.

This theory is prominent throughout culture to this very day. How far would you go in the search for knowledge, wealth, fame, youth, and power?

A lighter example is found in The Simpsons. First aired in October 1993, “Treehouse of Horror IV” follows the plot of Homer Simpson selling his soul for a donut.

So what did you sell your soul for?

If you could know the truth behind any secret or mystery, which would it be?

Nevada’s Area 51 Air Force base has been the epicenter of mystery for decades and is often the subject of alien conspiracy theories.

One thing is for sure, you’ll struggle to find an area more secretive. So what’s the deal?

What about the Bermuda Triangle, also known as the Devil’s Triangle? This area of the Atlantic Ocean between Florida, Bermuda, and Puerto Rico has been perplexing scientists for years.

With several planes and ships, reportedly disappearing from the region, what’s going on?

But wait, are we missing modern days’ biggest enigma—what are the eleven KFC herbs and spices?

You can time travel. What one event would you like to go back and witness?

For this question to work you should mention that you’re only there to witness the event.

Appearing at the Battle of Hastings in a Tweed jacket and Chelsea boots might make you stand out like a sore thumb.

Hypothetically, that could turn out traumatic.

So let’s remain inconspicuous for your time travel and look at some options.

In 80 AD, The Colosseum, one of the seven wonders of the world was complete. It would host many gladiatorial events. Visiting this amphitheater during this period would be an ideal way to see how the Romans lived.

Not a fan of watching people fight until death?

The year is 1215 in medieval England. King John is not a nice guy, he imprisoned his ex-wife and starved his opponents to death. Imposing heavy taxes on his barons, enough was enough.

His barons demanded he obeys the law and took London, forcing King John to negotiate. The result was the signing of the Magna Carta, which has since become a symbol of liberty around the world.

Maybe witnessing the signing of a document that has influenced society for years to come isn’t your bag?

Is there a stronger bond between a man’s love for his sports team? Did your football team lift the Super Bowl before you were born? Ancient history is wonderful, but would it compare?

If you could time travel, would you go forward or back in time?

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Have you ever wondered what life will be like in years to come?

Want to feel old? Of course you don’t, but sci-fi classic Blade Runner is set in November 2019. We thought it was a glimpse into our future, but now we’re here, where are the flying cars? 

So how different will it be? 

Not too long ago, a mobile phone was a brick that made calls. Now here we are with a computer in our hands, capable of several functions.

So will it be the past or the future? Someone should find out when we’ll get those flying cars.

If you could opt to be born at another time, when would you be born?

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On 8th May 1945, towns and cities across the world celebrated VE Day. Germany had surrendered, seeing an end to nearly six years of war.

Post World War II America boomed. The 1950s was a fruitful, prosperous period in America’s history contributing to the birth of Rock-and-roll and the golden era of Hollywood.

Fancy yourself hanging with Elvis or James Dean? Being a teenager in 1950s America would be cool.

But don’t forget the swinging 60s or the champagne 80s. Maybe this all too recent and you fancy yourself as a cowboy riding across the plains?

You can go back in time and uninvent something. What invention would you erase from history?

Be careful with this one. Have you seen Back to the Future?

“It’s the ripple effect!” – says Doc to Marty.

The ripple effect is the changing of the future by the slightest change in present events.

You may think banishing phones would have a positive impact, but how will you filter your face for your Tinder profile?

What about bombs? Surely if you uninvented the atomic bomb, that couldn’t have negative effects on the future—or could it?

Who would you most like to haunt you? 

Imagine having Thomas Jefferson’s spirit talking you through the inner working of a light bulb as you change the light in the kitchen.

Or Einstein’s presence aiding you through the complex algebra of your tax return. 

Or maybe Frank Sinatra’s apparition crooning to you on your morning commute.

While having a ghost linger might not seem like the best thing to happen, it might have its positives. I suppose it all depends on who you pick.

You’re a powerful figure in congress. What law would you abolish?

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You may not want to think of yourself as a member of Congress. But humor it for a moment. 

Are there any laws that should never see the light of day again? 

In Arizona, they passed a law prohibiting a sleeping donkey in your bathtub after 7 PM.

Abolish that one. What’s wrong with having a donkey in your bathtub?

Congress brought this law into effect in 1924, after a merchant used to let his donkey sleep in a bathtub. A dam broke, causing the town to flood with the donkey washed down the valley.

There’s a happy ending—-the donkey survived.

But the efforts and manpower used to save the donkey resulted in the passing of this law. Rumor has it there has been no further costly mule related rescue efforts.

What law would you pass?

Legalize marijuana? We’re not here to judge.

Every Friday off work? Why not?

Hang on, are we looking at this too lax?

The National Health Service (NHS) delivers healthcare for all UK citizens. They base the care you get on your needs rather than what you can afford. The UK isn’t alone with offering universal healthcare

Sound like a good idea?

Or is it time to focus on taxing the ultra-rich?

Amazon paid 1.2% on $13Billion in profits last year.

You pay, so why shouldn’t they?

It’s a brilliant question that can reveal how a person dreams of a better world or whether they just want Fridays off work.

You’re stranded on an island and have three things in your rucksack. What three items do you want to find?

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Are you thinking of taking a smartphone to ring for help?

Wiseguy, huh?

Don’t forget to bring your charger.

Did we mention that this island has no signal? You’ve wasted two items. 

Oh well, a few games of candy crush in the sun before your phone battery dies. 

The smarter reader will think of the apparatus needed to create a raft.

Is it possible to assemble a raft using three items? There are a lot of palm trees on this island.

It sounds like a lot of hassle, so why not enjoy your time on the island with your favorite book, a bottle of whiskey, and some suntan lotion?

You’re invited on the first passenger trip to the moon. Do you go?

British billionaire and Virgin Galactic founder Richard Branson is on a mission. Determined to ride into orbit on his spaceplane, he’s taking passengers with him and you’re invited—for free.

With tickets costing $250,000 how could you turn down the opportunity?

In 1968, Apollo 8 was the first crewed spacecraft to leave orbit and reach the moon. The focus had been on space, but it was the view of Earth that would have a lasting profound impact.

The fresh perspective of our planet has become such a powerful emotion the phenomenon has become known as the overview effect.

So a whole new perspective awaits you after a life-changing experience.

Why wouldn’t you do this?

The disastrous Virgin Galactic test flight in October 2014 might be worth mentioning. The craft broke up in flight, killing one crew member and seriously injuring another.

Not to mention, no doubt Richard Branson could be on board, so you risk having to sit next to him on a long haul flight.

I’ll let you weigh up the pros and cons.

Your house is on fire. What material possession do you save?

We’ll save you any awkward dilemmas and make this question about material possessions only. This way you won’t have to pick between your Mom or your Girl.

Unless you’re going out with Madonna, you can save her because she’s a material girl—I’ll get my coat.

You may have encountered this question before, and it’s interesting how many answers there are.

Ultimately, the answer will depend on an individual’s passions, so it’s a good way to get to know some better.

Would you live life differently if nobody could ever judge your actions?

“I ask you to judge me by the enemies I have made.” 

– Franklin D. Roosevelt

I’m sure you’d like to think of yourself as a lone wolf without giving a damn about others’ judgment.

But we know that humans can be a judgemental bunch.

Are you still in that job? Are you only earning that much? You’re still driving that?

This can damage our self-esteem, and bruised confidence will have a tremendous impact on our actions.

Wouldn’t it be great if we could give the two-finger salute to all the judgment thrown our way?

But is a little judgment a good thing?

The saying ‘no man is an island‘ expresses the idea we don’t fare too well in isolation. 

Do you have to separate the judgment? On one hand, it might be malicious hearsay, whereas we could see some judgment as advice to improve.

So without prying eyes and righteous judgment, how different would you live your life?

What would you do given 24 hours to live?

clock GIF

What if you woke up one morning to the news that today would be your last 24 hours, what would you do?

While the thought of our mortality can daunt, pondering this question can lead to inspirational life change. Life isn’t a guarantee, and we should value every minute.

Searching deep you may feel that true fulfillment is our interaction with loved ones. 

Whatever your findings, why not incorporate them into your life while you can?

If you could instantly become a master of any one skill. What skill would you pick?

With a click of the fingers, you’re a master of a skill. Best of all, you don’t have to sell your soul to the devil.

It’s difficult to hone a skill taking years of dedication and practice.

So without the years of banging your head up a brick wall, what skill would you become a master of?

Is there a language you’ve always wanted to learn? A musical instrument you long to play? 

Perhaps you want to paint like Van Gogh or meditate like Buddha.

Once you’ve uncovered your pick, why not devote a small amount of time each day? From small acorns grow gigantic oak trees.

The latest Hollywood blockbuster is a biopic about your life? Who stars as you?

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It’s worth asking this in a group because some answers will be hilarious.

It’ll be difficult to refrain from giggles when your friend, who’s no oil painting, claims Brad Pitt would be the perfect match.

As you’re all enjoying it, you could extend the laughs and add who’d star as your younger or older self.

Would you rather know a lot about a little or a little about a lot?

Have you ever heard the saying a “jack of all trades, master of none”? If you’re not familiar, it means someone who’s competent at most things but never master’s one.

If you’re able at most things can you excel in a certain area?

There might be an element of truth in the saying.

But what would set you up for success?

Being a fountain of knowledge in a specific area or being adept at everything?

If you were guaranteed an honest answer to one question, what would you ask, and to whom?

“Hi, Marilyn Monroe. Did the CIA kill you?”

Conspiracy theorists love this one. Did Marilyn Monroe’s involvement with John F. Kennedy lead to her death?

Claims suggest the overdose was a fake so she wouldn’t reveal state secrets. This theory had some weight when a retired CIA allegedly admitted to the murder on his deathbed.

Talking about Marilyns:

“Hi, Marilyn Manson. Is it true you have ribs removed so you could..?”

I suppose some things are best left unknown.

So what will you discover?

If your country was carving a new Mount Rushmore. Which four figures from politics, art, and culture would you want to be displayed?

presidents day candy GIF by Trolli

Not that Washington, Jefferson, Lincoln, and Roosevelt aren’t good enough. But who do you think represents the genuine spirit of your nation?

Are there any modern-day pioneers that deserve their face chiseled into a rock?

This question will depend on your nationality but is quite the conundrum. You’ll it’s surprised at the answers that’ll pop out.

Be open to discussion. If your cousin wants a sixty-foot sculpture of Bon Jovi, so be it.

What dystopian future would terrify you most?

Let’s close our best hypothetical questions by talking about an imagery society full of suffering.

Talking about dystopian futures can open the door to deep discussion. What’ll be the most likely dystopian future? How would you handle it?

But let’s start with the one that scares you the most.

The Hunger Games isn’t too pleasant, is it? I suppose having to navigate The Purge could be a little disconcerting. Fancy starring in The Truman Show? Are we already living in 1984?

That’s without contemplating the threat of zombies or AI.

20 Funny Hypothetical Questions

You may have found some of the best questions are a little funny. And I personally like that—there’s nothing wrong with a dark sense of humor. 

But now, here are my favorite hypothetical questions specifically designed to make people laugh.

  1. If Jurassic Park were real, would you visit?
  2. If you were a pirate, what would be your name?
  3. If you were a tree, what type would you be and why?
  4. What fictional bar would you like to have a drink in?
  5. What fantasy creature would you like to bring to life?
  6. If you had to have sex with a cartoon character, who’d it be?
  7. What animal would be the cutest if it was the size of a hamster?
  8. You can spend a day as the opposite sex. What do you get up to?
  9. If you were a transformer, what vehicle would you transform into?
  10. If you were a vampire and had no reflection, how would you do your hair?
  11. What one embarrassing moment would you go back and change if you could?
  12. You’re reincarnated as an animal with a similar personality to yours, what animal?
  13. If every time you entered a room, you had entrance music. What would be the song?
  14. You’re a mad scientist. What experiment would you run if money and ethics weren’t an issue?
  15. If you were to release your own fragrance, what would it smell like and what would you call it?
  16. Which of the seven dwarves would you be? Sleepy, Grumpy, Happy, Sneezy, Dopey, Bashful, or Doc?
  17. If your girlfriend was a florist and chocolate didn’t exist, what would you buy her to say you’re sorry?
  18. You’re out with a group of people and the conversation bores you. What would you say to change it?
  19. A witches’ spell has turned you into an inanimate, non-electric object. To break the spell you need to get a hundred people to touch you, what object would you be?
  20. You can choose one celebrity to kiss, one to marry, and one to kill. Who are they?

15 Weird/Crazy Hypothetical Questions

Craziness is on the menu with these head scratchers. Let’s creep over to the even weirder side of hypothetical questions. 

  1. You can pick three companions during the zombie apocalypse. What would be their professions?
  2. Talking of the zombie apocalypse, what would be your weapon of choice?
  3. If you were invisible for a day. Where would you go?
  4. Would you be cryogenically frozen if given the opportunity?
  5. If you could bring one person back from the dead who’d it be?
  6. If you could teach your pet a phrase? What would you want it to say?
  7. If you went to prison, would you focus on physical fitness or reading books?
  8. If you had to live in a TV show for one week, which show would you choose?
  9. What product would you stockpile if you discovered they were going to stop selling?
  10. If you were a superhero, what would be your power?
  11. If you had to invent a superpower that no superhero has used, what would it be?
  12. You’ve gone missing and your family and friends discover that you’ve joined a cult. What type of cult is it?
  13. You’ve time-traveled back to the year 1500 with no clothes or possessions. How do you prove you’re from the future?
  14. If you were wealthy beyond your wildest dreams, what eccentricities would you indulge in?
  15. You’re outside a bank when a robber runs outside. He passes you $10,000 to keep quiet. You’re guaranteed no repercussions. Would you keep it?

15 Random Hypothetical Questions

Now for some randomness. Anything goes in this absurd list of hypothetical questions.

  1. If you could be a candy bar, which one would you be and why?
  2. If a turtle lost its shell, would it be homeless or naked?
  3. If you found a friendly alien in the woods, what would you do?
  4. Would you rather wear clothes 2 sizes too big or 2 sizes too small?
  5. If you could only speak one word for the rest of the day. What would it be?
  6. If you could speak in any accent for the rest of your life. What would it be?
  7. You can only wear one fashion brand for the rest of your life. Which one is it?
  8. You’re the sixth member of the spice girls, what is your spice handle?
  9. If you could go on a TV quiz show, which one would it be and how would you get on?
  10. Who’d win in a fight between two half-sized Bruce Lees and one full-sized Mike Tyson?
  11. Would you rather have photographic evidence that proved the existence of the Loch Ness Monster or Bigfoot?
  12. You’re the ruler of a new country, what do you call it?
  13. Who would you get to write the national anthem for your country?
  14. You have the task to get the cashier to give you a weird look. What three things would you buy at a grocery store?
  15. If you could make it compulsory for players to drink alcohol before they play. What sport would be the funniest?

15 Hypothetical Interview Questions

Hypothetical questions are commonplace in job interviews. You might need inspiration if you’re interviewing potential employees. You can also use this section to practice your answering skills. Either way, they’ll sharpen your tools in a job interview scenario.

  1. How would you react if your boss told you that you’ve failed?
  2. You’re leading a team, morale is low. How would you build team spirit?
  3. If you could pick one professional to mentor you, who would it be and why?
  4. What action would you take if you found your colleague stealing office stationery?
  5. Your boss has made a decision that you disagree with. How do you handle this situation?
  6. What would you do if you discovered your manager was withholding key information from you?
  7. You’re working as part of a team and two team members are having frequent arguments. What would you do?
  8. You take a call off a customer—they’re unhappy and behaving aggressively towards you. How do you react?
  9. If you could be a CEO of any major corporation. Which would you choose and what changes would you implement?
  10. It’s your 3rd anniversary with this company, what do you hope will be different about you then compared to now?
  11. You’re having a bad day and deadlines are tight. A fellow employee is late for the third time this week. Do you react? If so, how?
  12. Your coworker disagrees with your viewpoint about the direction of a project. What techniques would you use to persuade them?
  13. You have a new idea that you’re convinced will work. Your team isn’t as enthusiastic and opts not to pursue your idea. How do you react? 
  14. Your colleague is going away for a long weekend. They confide in you they’re planning to call in sick for a day. What would you do and why?
  15. You’ve made a mistake in your work that no one else has noticed. Would you address the error at the risk of slowing things down or ignore it to keep the task progressing?

15 Interesting Hypothetical Questions

Now for some interesting hypothetical questions that will appeal to your philosophical side. You may have to dig a little deeper into your moral compass for these.

  1. If a genie gave you three wishes, what would you wish for?
  2. If you didn’t know whether the genie would allow you to ask for more wishes or more genies, would you risk asking?
  3. The genie finally grants a wish to another person. Who would you give the wish to?
  4. Would you sooner end all wars or end world hunger?
  5. What would your teenage self say to your modern-day self?
  6. If you could go back in time and kill Hitler as a baby, would you do it?
  7. If you could live in anyone’s head for 15 minutes, whose would you live in?
  8. Would you become more intelligent if it was at the cost of your happiness?
  9. If you could go back and change one decision, what would it be?
  10. Would you prefer to know how and when the world ends or know how and when you die?
  11. When you die, you have two options: find out what’s next, or stay on Earth to wander alone for eternity. Which would you pick?
  12. You’re at the pearly gates. You need to say one good deed you’ve done to justify entry to heaven. What would you say?
  13. You read a book only to discover that it’s your life. Do you continue to read knowing you’ll know every aspect of your life?
  14. You’re ordered to practice one of the seven deadly sins daily. Which one would it be? Pride, greed, lust, envy, gluttony, wrath, or sloth?
  15. What one crime would you commit if you knew you had complete anonymity? Would your conscience get you even if the judicial system can’t?

15 Hypothetical Questions to Ask on a Date

It’s easy to talk a big game on Tinder, but you need to back it up with solid conversation skills come date night.

Whether it’s your first date or you’re wanting to make deeper connections, try these questions to get to know your date.

  1. How would you describe your life so far in 20 words or fewer?
  2. If you could overcome one fear, what would it be?
  3. If you could marry someone famous, who’d it be? 
  4. You’re asked to write a novel. What would it be about?
  5. What would you ask for if you knew the answer was yes?
  6. If you could have supreme knowledge of one thing, what would it be?
  7. You get to listen to one artist or band for the rest of your life. Who is it?
  8. If you could eat one type of food for the rest of your life, what would it be?
  9. Would you rather travel for the rest of your life or stay in your home state?
  10. If you could relive this year and change one thing, what would you change?
  11. You win $1,000,000. The catch is you have to spend it in a week. How would you spend it?
  12. Would you rather marry a 10 with an unpleasant personality or a 6 with a pleasant personality?
  13. Imagine I’m abducted by aliens. How long would you wait for me before you started dating again?  
  14. If you could live in one season for the rest of your life, would it be spring, summer, autumn, or winter?
  15. You’ve won 10 years of free unlimited services. You can pick either a masseuse, a chauffeur, or a top chef. Which one would you choose?

10 Dumb Hypothetical Questions

‘There’s no such thing as a stupid question’. It’s difficult to disagree with this popular phrase. The road to knowledge has wrong turns and sometimes we have to ask for directions.

These questions aren’t exactly the peak of philosophical thinking, and you won’t need to be Aristotle to answer them. But damn—they’ll entertain.

  1. Would you rather be uglier or dumber?
  2. What if everyone on Earth jumped at once?
  3. What if there were no hypothetical questions?
  4. If you were a car part, what part would you be and why?
  5. Would you rather dive into a swimming pool full of piranhas or sharks?
  6. Imagine if there are no women in the world for 24 hours. What would you do?
  7. Would you prefer to say everything that comes into your mind or say nothing again?
  8. You’re held at gunpoint and asked for a reason not to pull the trigger. What do you say?
  9. Aliens have taken planet earth, and they put humans in zoos. What do you want in your zoo enclosure?
  10. AI robots are at war with humanity. You’re suspected of being a robot. If you had to prove that you’re human, what would you say?

How to Ask a Hypothetical Question

Hypothetical questions are fun. Their jovial nature makes them a lighter alternative to the deeper existential questions.

There are a few tips worth considering before dropping them into a conversation.

1. Learn some questions you’ll remember

As much as I’d like to think otherwise, you most likely won’t have this article on hand at all points of your social life so it’s worth memorizing a few questions.

2. Be appropriate

Always find the questions for your audience. For instance, you’ll not want to instigate a conversation about getting it on with a cartoon character over a business meeting. Save that one for the bar.

3. Pick the right people

Your audience needs to be open-minded. You’ll get the most enjoyment out of hypothetical questions if your company is creative and fun. Intelligence comes in many forms, so don’t exclude someone because you think they’re not clever. 

4. Timing is everything

A relaxed atmosphere will open the door to ask. Whether that is at the start or end of the occasion is down to you. Use your instinct. When you feel confident in yourself and the company—-may the hypothetical force be with you.


There we have it, enough hypothetical questions to cover all eventualities. Hopefully, you’ve pondered, laughed, and everything in between.

Regardless of the scenario, everyone can use hypothetical questions to liven up the conversations. 

So why not give it a go?

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