99 Of The Best Hypothetical Questions Ever

Some of the best conversation starters are what would you do” scenarios. Ask a hypothetical question with friends, and you’re guaranteed some interesting answers. 

The goal here is to enjoy each other’s company while letting others see more of the way your mind works. 

To that end, enjoy our hypothetical questions list. You’ll see them grouped into subcategories according to the general mood or your particular preference.  

What is a hypothetical question? 

A hypothetical question is one that contains an assumption or an imaginary scenario. As the name suggests, it’s based on a hypothesis, however unrealistic it might be. 

When used in a less formal setting — as a conversation starter —  the goal is usually to get to know each other better or to pass the time pleasantly. These questions also get people thinking about their own assumptions and priorities. 

99 Hypothetical Questions to Ask 

Look through the following hypothetical questions examples and choose the ones that appeal to you most. Make your own list of favorites to ask friends and family. 

Best Hypothetical Questions 

1. If you could ask your future self from the year 2040 one question, what would it be?

2. If someone wanted to pay you $100K to spend one week in a dark room without eating or sleeping — with one other person — would you accept the offer?

3. Every day, ten things appear in your back yard. If all of them start with the same letter, what would you want that letter to be? 

4. If you were guaranteed a living wage, where would you live and what would you do?

5. If you could time-travel and meet your parents before you were born, what would you say to them?

6. How would it change the world if people were incapable of lying? 

7. If you could erase one thing from existence — along with all memory of it — what would you erase?

8. If you could pick up any musical instrument and play it beautifully, which would you want it to be?

2 women talking best hypothetical questions ever

9. What would you do if you could make one illegal thing legal and one legal thing illegal?

10. If you could choose and control your dreams, what would you dream about tonight?

11. What futuristic thing from a sci-fi book or movie do you wish really existed? 

12. If you could create your own reality TV show, what would it be like?

13. If you could have tickets to any show or event — for you and as many guests as you like — what would you see?

14. If you could go back and learn something sooner, what would you do and how would it change things?

15. If you could have free, unlimited service from a chef, a housekeeper, or a chauffeur for a year, what would you choose? 

16. Would you give up your first world perks to live in a third world country if you knew you’d be happy

17. If you were offered something that erased your body’s need for sleep, would you take it?

18. How would your life be different if the average life expectancy was 500 years? 

19. If you could send yourself from ten years ago a message lasting only ten seconds, what would it be? 

20. Would you live your life differently if you knew no one would judge you no matter what you did?

Funny Hypothetical Questions

21. In a zombie apocalypse, what would be your weapon of choice? 

22. If you were a superhero, which of your friends would be your sidekick, and what powers (or skillsets) would each of you have?

23. If you were a famous superhero, what would be worse: being stuck with a terrible superhero name or having to dodge lovesick fans at every rescue scene?

24. If you could design a prison planet for crooked politicians, what would it look like?

25. If you could put wings on any species of animal, which animals would fly? 

26. If you were required by law to get a full-body tattoo, what would it look like?

27. If you were a farmer, and you learned the animals were plotting against you, how would you gain their trust? Which animals would you appeal to first? 

28. If you had to be haunted for the rest of your life but you could choose the ghost that would haunt you, who would it be? 

29. Why do our feet smell and our noses run?

30. If you could make any animal the size of a chihuahua, what animal would you pick?

31. If you could be invisible but fart loudly every few minutes, how would you use that?

32. You wake up as a performer for a medieval king’s court. What do you do to entertain him?

33. If you could exchange the sounds your body makes for other sounds, what would you replace burping sounds with?

men talking while holding cup best hypothetical questions ever

34. For $100,000, would you go a month without showering or changing your clothes? 

35. How does anyone know whether it’s partly cloudy or partly sunny? 

36. If you had to wear a mask for the rest of your life, what kind would you wear?

37. If you were an animated character, which would you be and why? 

38. If someone offered a pill that would make you a super genius but would remove all the hair from your body, would you take it?

39. If you were in charge of product development for a major fast-food chain, what abomination would you create for it? 

Good Hypothetical Questions

40. If you could start this year all over again, what would you do differently? 

41. Do you think the world would be a better place if all land was connected? 

42. How long do you think you’d survive if shipments of food stopped entirely? 

43. If you could instantly learn any skill in the world, what would you choose? 

44. If you could level up one aspect of yourself (beauty, intelligence, confidence), but you had to decrease another aspect to the same degree, what would you do?

45. A distant relative offers you $1 million if you can use up $100K in 1 week. How would you spend the money if you couldn’t spend or donate it all at once?

46. If you could be CEO of a major corporation for a year, which would you choose and what changes would you make?

47. If you could go back to any age for a month, what age would you choose? 

48. If you were elected president of the United States, what would you do your first day in office?

49. If you owned a bar or a coffee shop, what would you name it, and how would you make it different from the competition?

50. You’re at Comic-Con with cosplay so realistic, it’s freaking people out. What are people calling you? 


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51. If you had to wear the same outfit for the rest of your life, what would you wear?

52. How would the world change if animals could talk? 

53. If you could go back in time and change one decision of yours, what would you do?

54. If Jeff Bezos gave you all his money, what would you do with it?

55. If your superpower enabled you to control one thing — excluding people — what would you choose?

56. If you could be reborn in any country as any gender or race, what would you choose?

57. If you went deaf, what sound do you think you’d miss most? 

58. If you could be the world’s best athlete in a particular sport, which would you choose?

59. If someone offered you an island where you’d have plenty of food for the rest of your life but no human company, would you take it?

60. If you could teleport to any place on Earth, where would you go first?

61. If you knew this was your last year on Earth, what would you do? 

Weird Hypothetical Questions

62. If you found out you were actually a lab-created human-alien hybrid, what special abilities would you want to have?

63. What weird thing would you normalize if you could? 

64. If everyone associated you with a particular scent, what would you want that to be?

65. If you were suddenly homeless and broke but you could make yourself invisible, what would you do first?

66. If you could make one meal flawlessly but the rest of your cooking was garbage, what would your one good meal be?

67. You’ve won a lifetime supply of food you used to love but now don’t. What is it?

68. If you had to be a monster one night a month, what kind of monster would you want to be? 

woman holding pregnant woman's belly best hypothetical questions ever

69. If you were a food, what would you be?

70. If you woke up one morning with wings, what would you do first?

71. What do you wish grew on trees — or houseplants?

72. Your roommate decorates the biggest wall in the living room with a giant U.S. flag. What do you do?

73. If you had to lose two limbs, which two would you rather lose?

74. If you could choose any historical figure to haunt a current world leader, whom would you choose as haunter and haunted? 

75. If you had to choose one band or singer to listen to for the rest of your life, who would it be?

76. How much would someone have to pay you each month to make you give up your mobile phone? 

77. If the only thing to stop a disastrous war between kingdoms was a loveless marriage between the princess of one kingdom and the prince of the other, should the marriage be forced?

78. If you could re-spawn at home after dying (like in a video game), how would that change the way you live your life? 

79. Would the world be better if technology were similar to what it was 200 years ago or if it were like the tech described in your favorite sci-fi movie or novel?

80. If you had to make your own clothes without a sewing machine, would you stitch something together by hand or wear a toga made of curtains or bedsheets? 

Fun Hypothetical Questions

81. What hybrid animal would make the perfect pet, and why?

82. If you had the same dessert every night after dinner, what would you want it to be?

83. What animated world would you want to live in for a day (or longer)? 

84. If you could have dinner with any movie character, who would be your first choice?

85. If you could replace the president with any historical character, whom would you pick?

86. If you could make someone else invisible for a week, whom would you pick? Why?

87. If you had to sleep on sheets made of deli meat or fruit roll-up, what would you do?

88. If you were a famous entertainer with a pseudonym, what would people call you?

89. If you could travel the universe, would you rather fly in a starship or walk through a stargate? 

90. If you could buy any existing .com domain name, what would you choose and why? 

91. If you could teleport, but every time you did it, it cost you a year of your life, would you do it? 

women in robes laughing best hypothetical questions ever

92. How would the world be different if advertising didn’t exist? 

93. You’re reading a book and you discover it’s about your life. You get to the point where you are now. Would you turn the page?

94. According to a fortune-teller who’s never been wrong, something big is about to happen that will change your life. Do you want to know what it is?

95. Would you rather live a short life full of adventures or a long life without any?

96. If you could ask your past self from 10 years ago a question, what would you ask?

97. Would you take a job that paid you $50K a month to sit on a chair and do nothing for 8 hours a day 5 days a week with nothing to entertain you?

98. If you could communicate with animals, what would you for a living?

99. If you had absolute power for a day, what would you do with it?

How will you use these hypothetical questions?

Now that you’ve looked through these 99 hypothetical questions, which ones are you most likely to ask someone when you get the chance? 

Make your own list, using this one as a reference. Or keep this list handy for the next time you want to send a hypothetical “pop quiz” to someone via text message or social media post. 

Be prepared to answer them yourself if asked. That’s part of the fun. 

A hypothetical question is one that contains an assumption or an imaginary scenario. It’s based on a hypothesis, however unrealistic it might be.

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