100 hypothetical questions that spark great conversations

Hypothetical questions ask “what would you do if…?” They are great conversation starters because there is no wrong answer, nobody has to share anything private, and the answers say a lot about how someone thinks.

Fun hypothetical questions

1. If you could have any animal as a sidekick, which would you choose?
2. If you could live in any film or series for a week, which one?
3. If you had to eat one meal every day for a year, what would it be?
4. If you could instantly become an expert in one thing, what would it be?
5. If you could have dinner with three people, living or not, who would they be?
6. If you were invisible for a day, what would you do?
7. If you could have any job for one day, which would you pick?
8. If you could only listen to one album for the rest of your life, which one?
9. If you could design a holiday, what would people celebrate?
10. If your house could have one magic room, what would it do?
11. If you could swap lives with a fictional character for a day, who would it be?
12. If you could shrink or grow anything, what would you change the size of?
13. If you started a band, what would it be called?
14. If you could be any age for a week, what age would you pick?
15. If you could learn one instrument instantly, which one?
16. If you could make one food healthy, what would it be?
17. If you had a robot helper, what is the first task you would give it?
18. If you could star in any game show, which would you choose?
19. If you could replace one everyday object with something better, what would it be?
20. If you had your own island, what would you name it?

Superpower questions

1. If you could have one superpower, what would it be and why?
2. Flying or teleporting?
3. If you could read minds, would you want to switch it off sometimes?
4. Would you rather be super strong or super smart?
5. If you could stop time, what is the first thing you would do?
6. Would you want to be able to talk to animals? Which animal first?
7. If you could breathe underwater, where would you explore?
8. If you could heal others but not yourself, would you take the power?
9. Would you rather see the future or change the past?
10. If your superpower came with a weakness, what would you accept?
11. Would you rather be invisible or be able to fly?
12. If you could copy one skill from anyone you know, what would it be?
13. If you could move objects with your mind, what would you do first?
14. Would you want to live forever if everyone else did not?
15. If you had a superhero costume, what would it look like?

Time travel questions

1. If you could visit any time in history, when would you go?
2. If you could meet your future self, what would you ask?
3. Would you rather see the dinosaurs or the far future?
4. If you could relive one day of your life, which would it be?
5. If you could give your younger self one piece of advice, what would it be?
6. If you could witness one historical event, which one?
7. If you could bring one invention back to the past, what would you take?
8. Would you want to know how your life turns out?
9. If you could live in any decade, which would you choose?
10. If you could undo one invention, would you? Which one?
11. If you could spend a day in the year 3000, what would you look for first?
12. If you could fix one mistake from history, what would it be?
13. Would you go back in time to meet your grandparents when they were young?
14. If you could fast-forward through one part of life, would you?
15. If you could pause your life for a year without anyone noticing, what would you do?

Money and luck questions

1. If you won a million dollars tomorrow, what is the first thing you would do?
2. If you had to give away a million dollars, who would you give it to?
3. If money were no object, where would you live?
4. If you could get paid to do any hobby, which one?
5. Would you take a job you love for half the salary?
6. If you found a wallet full of cash, what would you do?
7. If you could have unlimited money for one purpose, what would you choose?
8. Would you rather have more money or more free time?
9. If you could open any business, what would it be?
10. If you had to spend a thousand dollars in one hour, what would you buy?
11. If you inherited a castle, would you live in it or sell it?
12. If you could guarantee one thing about your future, what would it be?
13. If you were famous, what would you want to be famous for?
14. If you could retire tomorrow, what would your days look like?
15. Would you rather be lucky or talented?

Weird hypothetical questions

1. If animals could vote, which one would win an election?
2. If you woke up as a cat, how would you spend the day?
3. If gravity switched off for a minute every day, what would change?
4. If you could only whisper or only shout for the rest of your life, which would you choose?
5. If clouds were edible, what flavour would they be?
6. If your shadow came to life, what would it do?
7. If everything you drew became real, what would you draw first?
8. If you had to live in a giant fruit, which fruit?
9. If furniture could talk, which piece would have the best stories?
10. If you could only walk backwards for a week, how would you cope?
11. If the ocean were made of soup, what kind would you want?
12. If you could shrink your pet into a keyring, would you?
13. If every lie made your nose grow, how long would yours be by the end of today?
14. If you had a tail, what would you use it for?
15. If you swapped voices with the next person you talk to, what would you say?

Deep hypothetical questions

1. If you knew you could not fail, what would you try?
2. If you had one year left, what would you do differently?
3. If you could change one thing about the world, what would it be?
4. If you could know the answer to one question, what would you ask?
5. If you could only keep three memories, which would you keep?
6. If you had to leave home tomorrow and start again somewhere new, would you?
7. If you could be remembered for one thing, what would it be?
8. If you could live anyone else’s life, would you, or would you keep yours?
9. If nobody would ever find out, would you still do the right thing?
10. If you could talk to anyone who has died, who would it be?
11. If you could have a conversation with any version of yourself, which one?
12. If you had to give up either music or films forever, which would you keep?
13. If you could learn the truth about one mystery, which would you pick?
14. If you could choose to never feel one emotion again, would you? Which?
15. If your life were a book, what would this chapter be called?
16. If you could make one rule everyone had to follow, what would it be?
17. If you could relive your life with everything you know now, would you?
18. If you could solve one problem for everyone, which would you choose?
19. If you had to describe your ideal future in one sentence, what would it be?
20. If today were the start of a new chapter, what would you want it to be about?

Turning answers into a conversation

• Ask “why?” The reason behind an answer is always more interesting than the answer.
• Answer too. Share your own choice and compare.
• Add a twist. “Okay, you can fly, but only one metre off the ground. Still want it?”
• Move on when it runs out. Hypotheticals are warm-ups; follow whatever real topic comes up.

Hypotheticals work well with someone you have just met, because nobody has to share anything personal. Try one in a random text chat or on video. For more ideas, see random questions to ask and would you rather questions.