130 Hypothetical Questions: Fun, Deep and What-If Topics

A hypothetical question asks about something that hasn't happened and may never happen: "What would you do if...?" or "What if...?". It's not a trick and it's not rhetorical. It expects an answer, but nothing depends on it, so people answer honestly and often surprisingly.

That's why hypotheticals are great in a chat. They skip small talk, there are no wrong answers, and a light question ("If you could fly, but only at walking speed...") can tell you more about someone than "What do you do?".

Below are 130 hypothetical questions, grouped from light to deep, plus a set of hypothetical topics for longer discussions and a few tips on asking them well.

Easy warm-ups

1. If you could add one hour to every day, what would you do with it?
2. If your home could either clean itself or cook for you, which would you choose?
3. If you could master one hobby overnight, which one?
4. If you had to wear one colour for the rest of your life, what would it be?
5. If you could instantly be good at one sport, which would it be?
6. If every day were a weekend for a month, how would you fill it?
7. If you could rename yourself, what name would you pick?
8. If you could live inside any painting or photo, which one?
9. If your phone could only do one thing, what should it be?
10. If a famous chef cooked for you once, what would you order?
11. If you could make one season last all year, which one? 12. If you could know the answer to one question today, what would you ask?

Superpowers and magic

13. If you could fly, but only at walking speed, would you still use it?
14. If you could read minds but couldn't switch it off, would you want the power?
15. If you could pause time for everyone except you, what's the first thing you'd do?
16. If you could teleport, but only to places you've already been, where would you go most?
17. If you could understand every language but not speak them, would that be enough?
18. If you could be invisible for one afternoon, how would you honestly spend it?
19. If anything you wrote in a notebook about yourself came true, what would you write first?
20. If you could breathe underwater, where would you explore?
21. If you could choose the weather in your town once a week, what would you pick?
22. If you could swap lives with someone for one day, whose would you pick?
23. If your superpower only worked on Tuesdays, which power would you want?
24. If you could give one superpower to your best friend, what would it be?

Time travel

25. If you could watch any moment in history in person, which would you pick?
26. If you could send one text message to your past self, what would it say?
27. If you could visit 100 years in the future for one day, what would you check first?
28. If you could relive one ordinary day from your childhood, which one?
29. If you could bring one object from the past into today, what would it be?
30. If you could meet one of your great-grandparents when they were your age, what would you ask?
31. If you could skip forward one year, would you? Why or why not?
32. If you could undo one invention, which would it be?
33. If you had lived 200 years ago, what job do you think you'd have had?
34. If you could see your life at 80 for one minute, would you look?

Money, work and luck

35. If you won a large prize tomorrow, what's the first boring thing you'd do with it?
36. If every job paid the same, what would you do for work?
37. If you could open a small shop anywhere in the world, what would you sell, and where?
38. If you had to give away a large amount of money in one day, how would you do it?
39. If you could try any job for one week, which would it be?
40. If you could work four days a week but earn a bit less, would you?
41. If you had to live on a small budget for a year, what would you cut first?
42. If you could be well known for one thing, what would you want it to be?
43. If you could have a mentor from any field, who would it be?
44. If you could retire tomorrow, what would your first month look like?
45. If you were given a free plot of land, what would you build on it?
46. If you got paid for your favourite hobby, would it still be fun?

Food and daily life

47. If you could only eat food from one country for a year, which country?
48. If you could invent a new ice cream flavour, what would it be?
49. If coffee and tea disappeared tomorrow, what would you drink in the morning?
50. If you had a personal chef for one meal a day, which meal would you give them?
51. If you couldn't use your phone after 9 pm, how would your evenings change?
52. If you could live without sleep and feel fine, would you want to?
53. If your fridge could talk, what would it say about you?
54. If you could only keep three things in your room, what would they be?
55. If you had to move tomorrow, what would you pack first?
56. If you could change one rule where you work or study, what would it be?

Animals and nature

57. If you could talk to one kind of animal, which would you choose?
58. If you were an animal for a day, which one, and where would you live?
59. If you could bring back one extinct animal, which, and would it be a good idea?
60. If you had to live in a forest, a desert, on an island or in an arctic town for a year, which?
61. If a pet could talk for one hour, what would you ask it?
62. If you could plant a tree that grew any fruit you wanted, what would it grow?
63. If you could see one natural wonder tomorrow, which one?
64. If you could live in a treehouse or a houseboat, which would you pick?

Travel, places and languages

65. If you had to move to a country where you didn't speak the language, which country would you pick?
66. If you could spend one ordinary week living like a local somewhere, where and doing what?
67. If you could eat breakfast in one city, lunch in another and dinner in a third, which three?
68. If you could take one friend on a free trip anywhere, where would you go together?
69. If you could only travel by train for the rest of your life, where would you still want to go?
70. If you could add one word from another language to your own, which word?
71. If you could invent a holiday the whole world celebrates, what would it be about?
72. If you had to teach a visitor one custom from your country, what would it be?
73. If you could design a city from scratch, what would it have that yours doesn't?
74. If you could be a tour guide in any city, which would you pick?
75. If you woke up in a country where nobody spoke your language, how would you get breakfast?
76. If you could send a postcard to anyone in the world, who would get it?

Hypothetical topics for longer discussions

These "what if the world worked differently" topics are good for a group, or for a long chat where you both take sides.

77. What if everyone had to change jobs every five years?
78. What if nobody could lie for a day?
79. What if humans hibernated in winter?
80. What if everyone in the world spoke the same language?
81. What if the internet switched off for a month?
82. What if every adult spent one year living in another country?
83. What if school started at 20 instead of 5?
84. What if money didn't exist and everything was a trade?
85. What if you could see a number above everyone's head showing how kind they are?
86. What if every town had one day a year when everything closed except the parks?
87. What if people could only send one message a day?
88. What if the weekend were three days everywhere?

"What would you do?" everyday dilemmas

Small, real-life choices. They show how someone thinks without getting heavy.

89. You find a wallet with cash and an ID. What do you do, step by step?
90. A friend asks your honest opinion on something they're proud of, and you don't like it. What do you say?
91. A shop gives you too much change. Do you go back?
92. You get two invitations for the same evening, one fun and one important. Which do you choose?
93. Your neighbour plays loud music on a Tuesday night. What do you do?
94. You're offered a job you'd love, but you'd have to move far from your family. Do you take it?
95. Someone cuts the queue in front of you. Speak up or let it go?
96. You're the only one who knows how to fix a problem at work, but it isn't your job. Do you fix it?
97. Someone you care about gives you a gift you really don't like. What do you do with it?
98. You can stay in an easy, comfortable job or take a hard one that teaches you more. Which?
99. A good friend forgets your birthday. Do you tell them?
100. You overhear a stranger giving a tourist the wrong directions. Do you step in?

Deep hypothetical questions

Save these for when the chat is going well.

101. If you knew you couldn't fail, what would you try first?
102. If you could keep only one memory, which would it be?
103. If your life so far were a book, what would the chapters be called?
104. If you could start your adult life again, what would you do differently?
105. If you could talk to your younger self for five minutes, what would you warn them about?
106. If you could choose never to feel one emotion again, would you? Which one?
107. If you lost all your possessions tomorrow, what would you miss most?
108. If you could be remembered for one thing, what would it be?
109. If you had to live by one rule for the rest of your life, what rule?
110. If you could see the world through someone else's eyes for a day, whose?
111. If you could change one thing about how people treat each other, what would it be?
112. If you could only talk to new people for a month, no old friends, what do you think you'd learn?

For more questions in this spirit, see our philosophy questions.

Would you rather

113. Would you rather know every language or play every instrument?
114. Would you rather always be ten minutes early or always twenty minutes late?
115. Would you rather have a rewind button or a pause button for your life?
116. Would you rather explore the deep ocean or outer space?
117. Would you rather live without music or without films?
118. Would you rather have a small flat in a great city or a big house in the middle of nowhere?
119. Would you rather be able to talk to plants or to machines?
120. Would you rather always read the last page of a book first, or never learn how any story ends?
121. Would you rather have a friend in every country or one very close friend next door?
122. Would you rather only whisper or only shout for a week?

Totally absurd

For when the chat needs a laugh.

123. If animals ran a city, which animal would be the mayor?
124. If your shoes could talk, what would they complain about?
125. If clouds had a flavour, what should it be?
126. If you were a ghost, which building would you haunt, and how politely?
127. If you could replace one sound in the world with another, what would you swap?
128. If your life had a laugh track, when would it play most?
129. If you were a vending machine, what would you sell?
130. If you shrank to the size of an ant for an hour, where would you go?

How to use hypothetical questions in a chat

1. Answer first, then ask. "I'd pick breathing underwater, I'd go straight to a coral reef. What about you?" is easier to reply to than a bare question.
2. Ask "why?" or "then what?". The answer is the start. The reason behind it is the conversation.
3. Go light to deep. Start with warm-ups or the absurd list. Move to dilemmas and deep what-ifs only once replies are long and relaxed.
4. Don't judge the answer. It's imaginary. If someone says they'd keep the wallet, ask what they'd do with it and laugh together.
5. Keep it clear in translation. Short sentences travel better than long, clever ones. "If you could fly, where would you go first?" works in any language.

Hypotheticals also make a good game: take turns asking one each and you have an easy version of the hot seat game. For questions to ask people you already know, see questions to ask your friends. For first messages, see our conversation starters for online chat.

Try one on someone in another country

Hypotheticals get even better when the other person lives somewhere very different: "If you could eat breakfast in any city..." has a different answer in Lagos, Lima and Seoul. With Olu you're matched in one tap with a real person who is online now in another country, and every message is translated both ways. It's text only, free, for adults 18+, and runs in your browser. If nobody is around, you may meet an AI local, always labelled as AI.

Pick one question from this page and try it on someone in another country right now.