65 Hypothetical Questions to Have a Fun Conversation

65 Hypothetical Questions to Have a Fun Conversation

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As opposed to rhetorical questions or loaded questions, hypothetical questions consist of unproven assumptions or make-believe scenarios. 

But you can also ask hypothetical questions to get to know someone better.  In fact, the right question can lead to a fun conversation as you learn interesting things about how another person thinks.

With that in mind, this article will talk about 65 hypothetical questions you can ask someone.

But first, let’s start with a quick definition.

What is a Hypothetical Question?

A hypothetical question deals with situations and circumstances surrounding what might happen or could happen, often leading the inquirer to include fictional parameters with the question regarding the things they suppose. 

People answer hypothetical questions based on supposition, views, their own beliefs, or conjecture—not facts, as the questions have no basis on reality. 

While people can ask hypothetical questions in a court of law or even during a job interview, making sure you know your audience best paves the way for asking hypothetical questions. 

Remember that asking hypothetical questions and listening to the answers can bring loads of fun, laughter, and a great chance to get to know other people if done timely, appropriately, and respectfully. 

So let’s dive into the specific questions you can ask: 

65 Hypothetical Questions to Have a Fun Conversation

Social Questions

  1. What laws would you create and abolish?
  2. If you could, what strange thing would you make acceptable in society?
  3. If everyone were incapable of lying, how would the world be different?
  4. If you could start a secret society, what would be its mission and who would be the members?
  5. Would you want to live in a world where the thoughts of every person appeared as a text message above their head?
  6. If you started an activist group, what would its goals be and what would you call it?
  7. If you could live in anyone’s head for sixty minutes, who would you choose and why?
  8. If you could ask anyone in history five questions, who would you choose and what questions would you ask them?
  9. Which color would you want to see for the rest of your life if humans lost the ability to see all colors except one?
  10. If you sent out one last text message to everyone in the world, what would it say?
  11. If you could make one thing that is legal and make it illegal, and vice versa, how would that change the laws?
  12. If you could designate a new holiday, what holiday would you create and what month would it appear on the calendar?
  13. If you could choose anyone in the world to become friends with, who would you choose?
  14. If you could redesign humanity, what parts would you change?
  15. If you could harmoniously unite two regions or two people, what two would you choose?

Professional Questions

  1. What company would you choose if you could be the CEO of any business?
  2. If you could be a professional athlete, what sport would you play?
  3. If robots could replace any job you chose, what would you choose? 
  4. What fashion trend would you start if you were a fashion icon?
  5. What kind of business would you like to start?
  6. If you joined the circus, what stunts would you like to perform? 

Time Travel Questions

  1. Would you snap your fingers if every time you snapped your fingers, you were instantly transported to a random point in humanity’s timeline?
  2. What advice would you give your parents if you could go back in time and give your parents advice before you were born?
  3. What argument would you choose to win if you could go back and win one you lost?
  4. What two-hour chunk of history would you want to watch if you could have a video? 
  5. What one word would you choose to put into any historical document? Where would you choose? 
  6. What would you tell yourself if you could call yourself when you were fifteen years old for a twenty-minute conversation?
  7. If you could forget your past, would you choose to know your future?
  8. What invention would you undo?
  9. If you could go back and erase one thing you did, what would you erase?
  10. When would you be born if you could choose the time you were born?

Personality Trait Questions

  1. If you could increase and decrease any characteristic about yourself in the same amount, what characteristics or traits would you choose?3
  2. Would you choose to become more knowledgeable if it meant you were largely unhappier?
  3. Would you rather be incredibly clever and sociable or subdued and intelligent?
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Animal Questions

  1. If you could put wings on any kind of animal, what animal would you choose?
  2. What two animals’ sounds would you like to swap with each other? 
  3. If your pet suddenly spoke one word and then never spoke again, what would be the most wonderful word you could imagine them saying?
  4. What species would you choose for extinction?
  5. What animal would be the cutest if all animals could be held and cuddled?
  6. If you could rename any three animals, what animals would you rename? 
  7. If animals became as intelligent as humans and could speak, what jobs would suit which animals?
  8. What animal would you bring into the world if you could create one?
  9. Based on your personality, if you were reincarnated as an animal, what animal do you think you would return as?

Life After Death Questions

  1. Which deceased person would you choose to haunt you? 
  2. After death, would you choose to go where death takes you or wander the earth forever without interacting with anything? 
  3. Where would you choose to haunt if you died and had to choose one place to haunt for the rest of eternity?
  4. If you could be reborn anywhere, anytime, as anyone, what would you choose?

Long Life Questions

  1. If extra lives were real, how would you obtain them?
  2. If you could add 100 years to your life, would you do it?

Food Questions

  1. What food would you be if you were food?
  2. If you could make one thing taste like something else, what would it be?
  3. If you could only eat the same breakfast, the same lunch, and the same dinner daily—all different meals– what three meals would you choose?
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Superpower Questions

  1. If you could be permanently invisible, would you choose to be?
  2. If you were a superhero/villain, what would your name be?
  3. What element would you choose to control if you could only control one? 
  4. What would you do if you were suddenly given high-end hacking know-how and capability?
  5. If you could get a full eight hours of sleep and yet still finish simple tasks while sleeping, what would you want to get done?
  6. What would you do with your superpower if it were to give phobias to people? 
  7. If you had a pencil with magical ability, what would happen when you used it?
  8. How would you use your power if you knew when and how someone would die just by shaking their hands but could not change their fate?
  9. What would your miracle medicine be if you could concoct a medication that could cure one thing?
  10. If your tears could cure cancer in one person, what would you do?
  11. What would be the first five things you would try if you were resilient to physical harm?


  1. What would your pseudonym be if you worked in the entertainment industry?
  2. What actor or actress would play your role in the film about your life?

Final Thoughts on Hypothetical Questions

These kinds of questions can make conversations fun, light, and engaging. By asking these questions, not only do you get to know the sides of other people you may not have otherwise known, but you have a chance at introspectively observing your own responses, and discovering more about yourself in the process. Now, if you want to find more fun questions to ask someone, be sure to check out our article on 371 deep questions to ask someone.

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65 Hypothetical Questions to Have a Fun Conversation