Select Page

funny hypothetical questions - Featured

26 Best Funny Hypothetical Questions - Spark fun conversations.


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, iHeart Media, Elite Dai ...
Read Full Bio

More about Mantelligence 's Editorial Policy

by | July 14th, 2021

Discussing entertaining and thought-provoking scenarios with your friends or family can be a great time. Asking the right hypothetical questions can keep a conversation going for hours, but what happens when you run out of funny questions to ask? You don’t want the conversation to become stale and boring.

Fear not, as we have a variety of different questions to ask to keep the conversation alive.

You’ll find everything from funny hypothetical questions to scenarios that will really make your head whirl.

Check out this long list of funny hypothetical questions you can ask your friends, or simply contemplate on your own!


4 Best funny hypothetical questions

The best funny hypothetical questions are really hard to come by; they wouldn’t be the best after all. If the best is what you’re looking for, then check these questions out, and rest assured you’ve got some of the most top-of-the-line hypotheticals.

Here are the 4 best funny hypothetical questions:

1. If Jurassic Park were real, would you visit it?

If any of the films are an indication of what would happen, I think it would be best to avoid such a potentially dangerous place.

2. If you were really a robot, would you want to know?

You could be a robot right now, and not even know it. This is also a question that is raised in the film “Blade Runner”. The main character might be a robot, but he doesn’t know that, and neither does the audience!

3. Would you rather be bald or have a huge mullet for the rest of your life?

So would you rather be a Bruce Willis or a Billy Ray Cyrus? Both choices are pretty good in my opinion.

4. Would you rather forget who you were or who everyone else was?

Maybe forgetting who you were would let your inner Jason Bourne come out? Either way, both possibilities are equally terrifying to think about.

4 funny hypothetical Conversation Starters Questions

Having trouble breaking the ice with someone you just met? Or maybe you’re just having trouble getting a conversation started? Sounds like you should check out these conversation starters questions and get chatting.

Here are 4 funny hypothetical conversation starters questions:

5. If you were a transformer, what vehicle would you turn into?

A difficult question when you realize transformers can transform into literally anything. It all depends on personal opinion. Would you rather fly around in a fighter jet, or mess around with people as a water fountain (for some reason)?

6. If you could be the CEO of any company, what company would you choose?

I’m sure the first choices for this question would include companies like Google, Amazon, or Facebook. I challenge you to think of different ones that aren’t as common.

7. If you were a dictator of a small country, what crazy dictator things would you do?

This question is a great way to find out which of your friends might secretly be an insane dictator. Maybe that’s what makes it a fun question to answer!

8. If you could move anywhere and still have a livable wage, where would you like to move?

A good question for all your traveler friends. What’s your dream location to live in? Is it somewhere in Europe? Iceland? Somewhere in South America? An underground society beneath Antarctica?

4 funny hypothetical Questions to Ask a Girl

Sometimes, certain hypothetical questions don’t interest some girls. Do you still want to keep a conversation lively, but are in a group with the majority of them being girls? Check out these questions to ask a girl so everyone has a great time.

Here are 4 funny hypothetical questions to ask a girl:

9. Would you rather have to say everything that comes to your mind or never say anything again?

Sometimes it’s best to say nothing at all. However, some people really appreciate those who speak their minds. When a balance of both isn’t possible, then it really makes you think about what kind of person you want to be.

10. If you could go back and be any age you want for a month, what would you choose?

Do older people want to go back to being younger and do younger people want to grow up faster? This is a great question to see if these statements are true.

11. If you had to be stuck in a TV show for a month, what show would you pick? And what character would you be?

An endless question to ponder. There are THOUSANDS of shows, both live-action and animated. Want to be in the World of Gumball? Or maybe you prefer The Office? Maybe being a character in Black Mirror sounds interesting? Actually, scratch that; I don’t know if that’s a good idea.

12. Would you rather live in the Harry Potter world or the Twilight world?

Both are equally dangerous and mysterious. But also, both are equally magical and fantastic. Who’s to say we aren’t already living in one of these worlds and just don’t know it?

4 funny hypothetical Questions to Ask Friends

Looking for some hypothetical questions to ask the people you’re hanging out with? If you’re looking to make a conversation entertaining, then check out these questions to ask friends. You’ll be sure to keep your pals laughing the whole time!

Here are 4 funny hypothetical questions to ask friends:

13. If you could only wear one piece of clothing for the rest of your life, what would it be?

So the real question is: do you want to become a cartoon character for the rest of your life? Characters in cartoons always wear the same outfit without fail! I already only cycle through the same 4 outfits, so I guess I’m halfway there.

14. Friendship or relationship, which would you choose?

A very interesting question that’ll reveal what your friends care about more. Is it romantic feelings that matter more? Or is a friendship more important?

15. You receive the power to grant a single wish to another person. Who would you grant the wish to? Why?

Imagine being a discount genie that can only grant one wish. I would urge the person to grant a wish that summons a real genie so they get 3 wishes. But that’s just me..

16. Would you rather be immortal but is unhappy or live only for fifty years of incredible happiness?

If I learned anything from Vampire movies, it’s that despite their amazing powers and the ability to live forever, they’re happiness tends to fade over time. But then again, maybe not being able to die makes you happy?

4 funny but interesting hypothetical questions

Not every hypothetical question has to be ridiculous and funny. Some can really tease your brain and be really interesting to think about. If this sounds like what you’re looking for, then check out these interesting questions to ask.

Here are 4 funny but interesting hypothetical questions:

17. If it had to always be nighttime or always daytime, which would you choose? And why?

If you live in the arctic, you’ll know that day and night last for much longer than everywhere else in the world. If you’ve experienced living in those conditions, you’ll probably have a more solid answer.

18. Which one of Spring, Summer, Autumn, or Winter would you choose for the rest of your life?

Would this affect your enjoyment of certain holidays? Would Halloween be just as fun if it weren’t enjoyed in Autumn? Is Christmas as good as it is in the Summertime?

19. What would you teach if you just had to teach something?

It would be really interesting to teach something that you are terrible at. Who says you have to teach something you’re good at?

20. What if there were no seasons?

What would no seasons even feel like? Would every day just have the same temperature? Imagine the environmental chaos if there were no seasons. That would mean every place in the world has the same climate, and so certain products wouldn’t be able to be grown.

4 funny and random hypothetical questions

Hypothetical questions don’t have to follow a structure or make sense. Sometimes some randomness in these kinds of questions is best. If you want to throw in some curveballs with your hypotheticals, then check out these random questions to ask.

Here are 3 funny and random hypothetical questions:

21. Would you accept a $30k/week job offer where you get paid to sit in a pitch-black room and do nothing for 8 hours a day?

A lazy person would love this job. Sitting in a dark room doing absolutely nothing sounds like a great deal! However, would this eventually become boring? Would you want to waste that time not pursuing a real career?

22. If a zombie plague were to start right now, where would you hold up?

Some might say a mall is a good place to hole up in during a zombie apocalypse. Some say a police station. I think Iceland is a good place to be. Limited people equals limited zombies!

23. Would you give up true love for $10 million? $100 million?

This brings up what true happiness is. Does money bring you happiness, or does love? Most people would think that’s an obvious answer, but you’d be surprised how many people are truly happy when they have lots of money.

3 funny but deep hypothetical questions

Hypotheticals aren’t always fun and games. Some of them propose very deep and thought-provoking scenarios that take some time to think about. If that sounds like up your alley, then check out these deep questions to ask.

Here are 3 funny but deep hypothetical questions:

24. Would you feel uncomfortable going out to eat or to a movie by yourself?

A lot of people already do both these things in their homes by themselves. The question boils down to whether you care what people think of you or not.

25. If you never had to sleep again, what would you do with the extra time?

Hopefully, there would be no side effects. But imagine the possibilities of what you could get done with all that extra time. Or maybe you’d be just as lazy as you are during the day and just have more time to watch YouTube videos.

26. If advertisements didn’t exist, do you think the world would be different?

The world would have to be incredibly different just for this hypothetical scenario to exist. The way information is given to the public would have to change, marketing would be totally different, and maybe even the government would have to change to allow such a thing.

Downloadable List of Funny Hypothetical Questions

Here is a downloadable list of funny hypothetical questions (right-click the image and select Save Image As...):

How to Pick the Best Funny hypothetical questions

It can be a difficult task to pick the hypothetical questions that are worth your time. How do you choose the best hypotheticals when there are so many? Take a look at this simple-to-follow guide and you’ll have no trouble picking the very best funny hypothetical questions.

Here's how to pick the best funny hypothetical questions:

1. Don’t Just Pick Hypotheticals of the Same Topic

Hypothetical questions can take you through a vast amount of topics, so don’t just limit yourself to one stream of conversation. Don’t just pick hypotheticals about money, or traveling back in time. Mix it up a bit and you’ll be sure to have a great time.

2. Vary the Complexity of Questions

If you’re only choosing hypothetical questions that don’t make you think too hard or make you think way too much, then you’re doing it wrong. Vary the complexity of your questions so that you get a good balance of hypotheticals that are thought-provoking and very simple.

3. Pick The Most Absurd Hypotheticals You Can Find

The whole fun of hypothetical questions is thinking about ridiculous scenarios. With that in mind, why not choose the most insane and absurd questions you can possibly think of? That will be sure to keep you laughing and having fun for hours.

More Awesome Conversational Tips

  1. Do you like to stay up at night and wrack your brain over intriguing ideas? Then it sounds like these thought-provoking questions will be right up your alley.
  2. Are you struggling to come up with good questions to ask your crush? Check out these questions to ask a girl you like and see if they give you any ideas.
  3. If you feel like you have trouble starting conversations with girls, then these questions to ask a girl are definitely something you should check out!

In Conclusion

There is a massive amount of funny hypothetical questions to choose from, so it can be a difficult thing to narrow them down and find some really great ones. There is a lot of enjoyment to be had from hanging out with friends and laughing over funny questions to ask and hilarious hypothetical questions. Whether it be entertaining yourself with simple “what ifs” or complex and insane scenarios that couldn’t possibly happen, it is always interesting to know what people would do in such situations.

Going through these questions to ask is a great way to bond with people and find out things about yourself. The crazier they are, the better!

Hopefully, you were able to find some truly thought-provoking and funny hypotheticals to ponder in your own head or to have fun with friends with!

smiling-woman 2 v4


85 Proven


printable checklist

Free list of questions to ask

smiling-woman 2 v4


How to Talk to Any Girl

...and get her to like you!

Free series of tips & proven convo starters

Skip to content