135 Hypothetical Questions to Have a Fun Conversation

What would you do if you could live anywhere in the world for a year? Or wake up tomorrow with a completely different skill?

Questions like these can turn an ordinary conversation into something much more interesting. Hypothetical questions invite people to imagine different situations, explore possibilities, and reveal how they think, what they value, and what they might do when faced with unexpected choices.

They’re also a great way to break the ice. Whether you’re getting to know a new friend, spending time with family, or looking for fun conversation starters, the right hypothetical question can lead to surprising answers and plenty of laughs.

Of course, not every hypothetical question has to be serious. Some can spark thoughtful discussions, while others are simply weird, funny, or completely impossible. That’s part of the fun.

In this article, you’ll discover 135 hypothetical questions covering a variety of topics and scenarios. Use them to start conversations, get to know someone better, or simply see where an imaginative question takes you.

And don’t forget to download the free SMART Goals Worksheet at the end of the article. It’s a helpful tool for turning your ideas and ambitions into clear, actionable goals.

Let’s start with a quick look at what makes a question hypothetical.

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 (as opposed to logic questions).

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: 

135 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?
16. If you were about to be killed and were only allowed to say goodbye to one person on the telephone, who would it be? And what would you tell him or her?
17. If you could go back to college for free, would you change your major? What would you pick?
18. If you could tell your romantic partner one negative thing about them without hurting their feelings, would you?
19. If you could be a kid again for just one day, would you? Which age would you choose to be?
20. If you could pick one professional sport to get rid of, which would you choose and why?
21. If you had to give up all technology (smartphones, tablets, fitness trackers, computer, tv, iPod, etc…) or alcohol for the rest of your life, which one could you live without?
22. If you could own any car in the world, which year, make and model would you choose?
23. Which is the one place on earth you would never want to live and why?

Professional Questions

24. What company would you choose if you could be the CEO of any business?
25. If you could be a professional athlete, what sport would you play?
26. If robots could replace any job you chose, what would you choose?
27. What fashion trend would you start if you were a fashion icon?
28. What kind of business would you like to start?
29. If you joined the circus, what stunts would you like to perform?
30. If you were to wake up one morning suddenly having full knowledge to work in any other profession, which profession would you choose? Why?
31. If you could make your boss suddenly disappear without any ramifications, would you? 
32. If there was one co-worker you could anonymously vote to have fired and add their salary to your own, would you? If so, who would you choose and why?  
33. Is there any job you would never do, no matter how much money you were being offered? Which job? Why?
34. Would you rather be President of the United States or the Leader of a Monarchy? If Monarchy, where would you rule?

Time Travel Questions

35. Would you snap your fingers if every time you snapped your fingers, you were instantly transported to a random point in humanity’s timeline?
36. What advice would you give your parents if you could go back in time and give your parents advice before you were born?
37. What argument would you choose to win if you could go back and win one you lost?
38. What two-hour chunk of history would you want to watch if you could have a video?
39. What one word would you choose to put into any historical document? Where would you choose?
40. What would you tell yourself if you could call yourself when you were fifteen years old for a twenty-minute conversation?
41. If you could forget your past, would you choose to know your future?
42. What invention would you undo?
43. If you could go back and erase one thing you did, what would you erase?
44. When would you be born if you could choose the time you were born?
45. If you could travel back in time and bring your first true love back to live in the present with you, would you?
46. If you could travel to the future and be there for your own funeral, would you want to?
47. If you could travel back in time and spend one day with someone you lost, who would you spend that day with and why?
48. If you could travel back in time to experience any war, with the guarantee of never getting hurt, would you? Which war?
49. If you could travel to the future to experience life on any planet you choose, but could never come back to Earth, would you take the ride?

Personality Trait Questions

50. If you could increase and decrease any characteristic about yourself in the same amount, what characteristics or traits would you choose?3
51. Would you choose to become more knowledgeable if it meant you were largely unhappier?
52. Would you rather be incredibly clever and sociable or subdued and intelligent?
53. Would you rather be rich or blissfully happy?
54. If you could change one physical feature about yourself without anyone noticing, would you? Which feature?
55. If you could commit one crime in your life without being caught, would you? Which crime and why?
56. Could you ever kill an animal who was suffering? Or would you just get help?
57. If your partner could read your mind, would they still want to be with you?
58. If you could live in good health to be over 100, but lose the ability to ever tell a lie, would you want to live longer?
59. If you could make a deal with the devil, which of these would you consider giving up your soul for?
    1. Being the smartest person in the world
    2. Being the wealthiest person in the world
    3. Being the most beautiful person in the world
    4. Being the most famous person in the world
    5. None. I’m happy with who I am
60. If you were granted three wishes by a genie right now, would you spend them all on yourself or on others? 

Animal Questions

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

Life After Death Questions

70. Which deceased person would you choose to haunt you?
71. After death, would you choose to go where death takes you or wander the earth forever without interacting with anything?
72. Where would you choose to haunt if you died and had to choose one place to haunt for the rest of eternity?
73. If you could be reborn anywhere, anytime, as anyone, what would you choose?
74. If you knew there was only a purgatory and eternal suffering would be only temporary, would you live your life any differently?
75. Would you rather spend an eternity in paradise completely alone watching video images of your loved ones, or be reincarnated?
76. If you could be reincarnated as an animal or a human being, which would you choose?
77. If you were given one chance to be reborn and could choose a different sex and race, would you? If so, which would you choose and why?
78. What is the first question you would ask God after you died?

Long Life Questions

79. If extra lives were real, how would you obtain them?
80. If you could add 100 years to your life, would you do it?
81. Would you rather live to be 100, but remember nothing at the end, or die sooner with your memories intact?

Food Questions

82. What food would you be if you were food?
83. If you could make one thing taste like something else, what would it be?
84. 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?
85. If you could change the smell of one food, which would it be?
86. If a roach tasted like your favorite food, would you try it?
87. If you had to give up your favorite food to keep your smartphone or tablet, would you?
88. Have you ever not tried a food because of how it looked? Which one?
89. If your favorite food in the world suddenly smelled like farts, but tasted the same, would you still eat it?

Superpower Questions

90. If you could be permanently invisible, would you choose to be?
91. If you were a superhero/villain, what would your name be?
92. What element would you choose to control if you could only control one?
93. What would you do if you were suddenly given high-end hacking know-how and capability?
94. 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?
95. What would you do with your superpower if it were to give phobias to people?
96. If you had a pencil with magical ability, what would happen when you used it?
97. 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?
98. What would your miracle medicine be if you could concoct a medication that could cure one thing?
99. If your tears could cure cancer in one person, what would you do?
100. What would be the first five things you would try if you were resilient to physical harm?
101. If you could be shot with bullets anywhere and survive, but be left with the holes in your body, would you want that ability?
102. If you had the power to make an unattractive man or woman walk again by having sex with them, would you do it? 
103. If you had the power to heal, but would hear screams in your head for two hours afterwards, would you?
104. If you were given the opportunity to have any superpower you desire, with the caveat of not being able to heal any of your family members, would you still want that power?
105. If you could choose between superhero and villain, which would you choose? Do you have more people you want to harm or help?

106. What would your pseudonym be if you worked in the entertainment industry?
107. What actor or actress would play your role in the film about your life?
108. If you were an author, would you use your real name or a pseudonym? What would your pen name be?
109. If you were granted an interview with any celebrity in the world, who would you pick? What is the first question you would ask them?
110. If you could be famous for anything, what would that be?
111. If you could film a kissing scene with any actor, who would you pick?
112. Would you ever consider starring in a pornographic film? If so, would you have any conditions for doing so?
113. Do you believe that celebrities have a responsibility to use their money and influence to help others?
114. What genre of film best describes your current status in life?
115. What songs would be on the soundtrack of your childhood?

The Dark Side Questions

116. Have you ever secretly wished harm upon another person? What for?
117. Have you ever wished that a sibling had never been born?
118. If you could hunt down one violent criminal and get away with murdering them, would you?
119. Do you believe in revenge? What actions do you believe are deserving of revenge?
120. If you were being held hostage, which form of torture would you be most afraid of?
121. If your spouse gave you a hall pass for 48 hours, how would you use it?
122. What is the one thing you’d like to do that you’d be too embarrassed to tell your partner about?
123. What is the one sexual act you’d never try?
124. What is one sexual act you’d like to try but are afraid to ask your partner?
125. Do you believe that ghosts can cause nocturnal emissions?
126. Have you ever found a much older person sexually attractive? How much older were they?
127. If you could look at any type of pornography without repercussions, which type might you fancy?
128. Would you ever consider paying for sex?
129. If you had to give up sex or technology, which would you give up?
130. If you were to do a strip tease in front of a magic mirror that could change something about your appearance, what would you change?
131. Have you ever found a person with the same sexual orientation attractive?
132. What song describes your sex life?
133. Is oral sex cheating if it’s on a blow up doll?
134. Have you ever found a cartoon hero attractive? Which one?
135. Have you ever fantasized about a friend’s significant other? Did you tell your friend?

Free Download: SMART Goals Worksheet

The SMART Goals Worksheet helps you turn ideas into specific, measurable, achievable, relevant, and time-bound goals. Use it to organize your priorities and create a practical plan for making progress.

Download your free worksheet and start turning your ideas into actionable goals today.

(The link opens up a Google Drive folder where you can get the PDF download in a variety of sizes: A4, A5, and US Letter.)

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 these other articles:

Finally, if you want to ask better questions, then watch this short, 20-minute course to learn how to have a great conversation with virtually anyone.