400 Hypothetical Questions to Ask [Never Run Out]

Hypothetical questions are like keys to the imagination. They unlock fun, deep, or even crazy conversations that help us explore new ideas, understand people better, or just have a good laugh.

Whether you’re chatting with friends, family, or someone special, these questions are your ticket to a chat full of surprises and insights. 

To Ask Your Boyfriend

1. If we could go anywhere in the world right now, where would you want to go?
2. What would you do if we won the lottery tomorrow?
3. If you could have any job in the world for one week, what would it be?
4. If you could eat only one food for the rest of your life, what would you choose?
5. What would you do if you found a treasure chest full of gold?
6. If you could be a superhero for a day, who would you be and why?
7. If you could time travel to any era, where and when would you go?
8. What would you do if you were invisible for a day?
9. If you could switch lives with anyone for 24 hours, who would it be?
10. If we were both animals, what animals would we be?
11. What would you do if you could fly?
12. If you had three wishes, what would you wish for?
13. If you could meet any historical figure, who would it be and why?
14. What would you do if you were the last person on Earth?
15. If you could be famous for one thing, what would it be?
16. If you could relive one day of your life, which day would you choose?
17. What would you do if you were king for a day?
18. If you could have any pet in the world, real or fictional, what would it be?
19. If you could live in any TV show or movie, where would you live?
20. If you could have any superpower, but only one, what would it be?
21. What would you do if you could read minds?
22. If you could change one law, what would it be and why?
23. If you had to eat only spicy food or only sweet food for a month, which would you choose?
24. What would you do if aliens landed in your backyard?
25. If you could be a famous musician, who would you be?
26. If you were stranded on a deserted island, what three things would you want with you?
27. If you could trade places with any fictional character, who would it be?
28. What would you do if you were a giant for a day?
29. If you could live in any country for a year, where would you go?
30. If you could have dinner with any three people, dead or alive, who would they be?
31. What would you do if you found a magic lamp?
32. If you were a pirate, where would you bury your treasure?
33. If you could choose the way you’ll die, how would you go?
34. If you could be any age for a week, what age would you be?
35. What would you do if you could talk to animals?
36. If you could be a character in any book, who would you be?
37. What would you do if you won a lifetime supply of your favorite food?
38. If you could be an Olympic athlete, what sport would you compete in?
39. If you could go to space, would you?
40. What would you do if you woke up and it was suddenly 10 years in the future?
41. If you had to listen to one song for the rest of your life, what would it be?
42. What would you do if you were a billionaire for a day?
43. If you could be any element on the periodic table, which one would you be?
44. What would you do if you could never feel pain again?
45. If you could only wear one color for the rest of your life, what color would it be?
46. What would you do if you had to live in a different time period?
47. If you could transform into any animal at will, which one would you pick?
48. What would you do if you found out you were related to someone famous?
49. If you could only watch one TV show for the rest of your life, which one would it be?
50. What would you do if you could control the weather?

To Ask Your Girlfriend

1. If you could be a famous actress for a day, who would you be?
2. What would you do if you suddenly gained the ability to time travel?
3. If you could live in any fictional world, where would you choose?
4. If you could swap lives with a Disney princess, which one would you pick?
5. What would you do if you found a doorway to another dimension?
6. If you were a wizard, what would your specialty be?
7. What would you do if you woke up with a magical singing voice?
8. If you could only read one book for the rest of your life, which would it be?
9. What would you do if you were president for a day?
10. If you had to live in a famous painting, which one would you choose?
11. What would you do if you could teleport anywhere instantly?
12. If you could be a world-class chef for a week, what kind of food would you specialize in?
13. What would you do if you found out you’re a princess from a far-off kingdom?
14. If you could be any flower, what kind would you be?
15. What would you do if we were stuck in a Groundhog Day loop?
16. If you could turn any activity into an Olympic sport, what would you have a good chance of winning a medal for?
17. What would you do if you could change one historical event?
18. If you were a detective in a mystery novel, how would you solve crimes?
19. What would you do if you found out you had a twin you never knew about?
20. If you could live underwater like a mermaid, would you?
21. What would you do if you found the Fountain of Youth?
22. If you could choose any vehicle (real or fictional) to drive, what would it be?
23. What would you do if you woke up as a character in your favorite video game?
24. If you could instantly master any musical instrument, what would it be?
25. What would you do if you found a map to hidden treasure?
26. If you could instantly speak any language fluently, which one would you pick?
27. What would you do if you could walk on water?
28. If you were a famous author, what kind of books would you write?
29. What would you do if you found out you had magical powers?
30. If you could be any mythological creature, what would you be?
31. What would you do if you were stuck in a fairy tale?
32. If you could experience life in a different period of history, when would that be?
33. What would you do if a genie offered you three wishes but you couldn’t wish for more wishes?
34. If you could bring any fictional character to life, who would it be?
35. What would you do if you found out you could breathe fire?
36. If you could have a one-hour conversation with any animal, what animal would you choose?
37. What would you do if you had an identical clone?
38. If you could choose the theme song of your life, what would it be?
39. What would you do if we could switch genders for a day?
40. If you could taste a color, what color do you think would be delicious?
41. What would you do if you were stuck on a deserted island with only a volleyball for company?
42. If you could choose to be a master at any type of dance, what style would you pick?
43. What would you do if you could become invisible at will?
44. If you could make one fictional device or gadget real, what would it be?
45. What would you do if you woke up in a post-apocalyptic world?
46. If you had to pick a planet to live on other than Earth, which one would it be?
47. What would you do if you could enter people’s dreams?
48. If you could live forever but had to give up one sense, which one would you lose?
49. What would you do if you were a contestant on a reality TV show?
50. If you had to fight in a medieval battle, what weapon would you choose?

To Ask Friends

1. If you could have a one-hour chat with any fictional character, who would you choose?
2. What would you do if you got stuck in your favorite video game?
3. If you could instantly become an expert at any sport, which one would you pick?
4. If you could replace the lead actor in any movie, which movie would it be?
5. What would you do if you woke up and everyone else was a zombie?
6. If you could be a contestant on any game show, which one would you pick?
7. What would you do if you could change your appearance at will?
8. If you could bring back any fashion trend, what would it be?
9. What would you do if you were suddenly the CEO of a big company?
10. If you could choose any animal to talk to, which one would you pick?
11. What would you do if you could control time, but only for five minutes a day?
12. If you could have any one gadget from a spy movie, what would you choose?
13. What would you do if you woke up in the world of your least favorite book?
14. If you could eat dinner with any three fictional characters, who would you choose?
15. What would you do if your life turned into a musical?
16. If you were a ghost for a day, who would you haunt?
17. What would you do if you found out you were a secret agent?
18. If you had to listen to one band or artist for the rest of your life, who would it be?
19. What would you do if you woke up in the future and you were a robot?
20. If you could have the talent of any famous artist, who would you choose?
21. What would you do if you had to survive in the wilderness for a week?
22. If you could be any kitchen appliance, what would you be?
23. What would you do if you woke up and found yourself in a horror movie?
24. If you could have any one item from a cartoon, what would it be?
25. What would you do if you could erase one thing from history?
26. If you had the chance to go to Mars, would you take it?
27. What would you do if you were suddenly able to levitate?
28. If you could replace one body part with a super-advanced prosthetic, what would it be?
29. What would you do if you found a time machine that only goes forward in time?
30. If you could choose the weather for one day, what would you pick?
31. What would you do if you had the ability to shape-shift?
32. If you could instantly have a PhD in any subject, what would it be?
33. What would you do if you could become any historical figure for a day?
34. If you could live in any sitcom, which one would you pick?
35. What would you do if you had the Midas touch?
36. If you could move to any planet in our solar system, where would you go?
37. What would you do if you woke up and your pet could suddenly talk?
38. If you could change one physical law, what would it be?
39. What would you do if you found out your life was a simulation?
40. If you could be a character in any comic strip, who would you be?
41. What would you do if you could see five minutes into the future?
42. If you could ride any mythological creature, what would it be?
43. What would you do if you could switch lives with your friend for a day?
44. If you had to live in a video game world, which one would you pick?
45. What would you do if you were suddenly the size of an ant?
46. If you could win any award, which one would you want?
47. What would you do if you could only travel by hopping like a kangaroo?
48. If you could be a famous YouTuber, what kind of videos would you make?
49. What would you do if you woke up and you were the last person your age on Earth?
50. If you could bring one fictional item into the real world, what would it be?

To Ask Your Crush

1. If you could plan the perfect date, what would it look like?
2. What would you do if you found a suitcase with a million dollars inside?
3. If you could star in any movie genre, what would it be? Romance, action, comedy?
4. What would you do if you could be invisible for one day?
5. What’s the first thing you’d do if you woke up as the opposite gender?
6. If you had the power to heal one illness in the world, what would it be?
7. What would you do if you could be a kid again for a day?
8. If you were a famous influencer for a week, what cause would you promote?
9. What would you do if you had the power to pause time?
10. If you could live the life of a famous athlete, actor, or musician for a day, who would it be?
11. What would you do if you could be the best chef in the world for 24 hours?
12. If you could pick any decade to live in, which one would you choose?
13. What would you do if you found out you had the ability to speak to animals?
14. If you could instantly acquire a new skill or talent, what would it be?
15. What would you do if you could see into the future but not change it?
16. If you were given the chance to be a contestant on any reality TV show, which one would you choose?
17. What would you do if you had to live without your phone for a month?
18. If you could wake up tomorrow fluent in any language, which one would you choose?
19. What would you do if you could switch lives with your favorite celebrity?
20. If you could have the answer to any one question, what would you ask?
21. What would you do if you found out that you had one week to live?
22. If you could instantly be at any place in the world right now, where would you be?
23. What would you do if you found a doppelgänger of yourself?
24. If you had to wear one outfit for the rest of your life, what would it be?
25. What would you do if you were given the opportunity to colonize Mars?
26. If you could instantly be the best player of any game, which game would you pick?
27. What would you do if you could relive any year of your life?
28. If you could choose to live in any TV show, which one would it be?
29. What would you do if you suddenly became a millionaire?
30. If you had the ability to change one thing about the world, what would it be?
31. What would you do if you were suddenly the smartest person in the world?
32. If you could choose any two famous people to be your parents, who would they be?
33. What would you do if you could eat without gaining weight?
34. If you could be a professional in any sport, what sport would you pick?
35. What would you do if you could choose the dreams you have every night?
36. If you had the power to eliminate one type of weather forever, what would it be?
37. What would you do if you found out you could live for 200 years?
38. If you could change your name to anything else, what would it be?
39. What would you do if you woke up with the ability to fly?
40. If you could turn any activity into your full-time job, what would it be?
41. What would you do if you found a real-life treasure map?
42. If you could instantly become friends with any one celebrity, who would it be?
43. What would you do if you had a magic carpet?
44. If you could be famous for inventing something, what would it be?
45. What would you do if you could make one rule that everyone had to follow?
46. If you could have any car in the world, which one would you choose?
47. What would you do if you had the power to make things come to life?
48. If you could bring back any TV show that was canceled, which one would you bring back?
49. What would you do if you could teleport but only once?
50. If you could be any age for a week, what age would you choose?

To Ask Your Parents

1. If you could have dinner with any three people, dead or alive, who would they be?
2. What would you do if you won the lottery tomorrow?
3. If you could relive one year of your life, which one would you choose?
4. What would you do if you were the President for a day?
5. If you could switch lives with anyone in history, who would it be?
6. What would you do if you found a magic lamp with a genie inside?
7. If you could live in any other country, where would you go?
8. What would you do if you were suddenly 25 years younger?
9. If you could only eat one type of food for the rest of your life, what would it be?
10. What would you do if you could travel back in time once?
11. If you had to live in a different time period, when would you choose?
12. What would you do if you could instantly learn any instrument?
13. If you could be any animal for a day, which one would you pick?
14. What would you do if you were suddenly a famous author?
15. If you could live in a fictional world, where would you choose?
16. What would you do if you found out you were a long-lost royal?
17. If you could choose one age to be forever, what age would you pick?
18. What would you do if you had the power to cure any disease?
19. If you could instantly master any craft, what would it be?
20. What would you do if you were given three wishes?
21. If you could have any job other than your own, what would it be?
22. What would you do if you could fly anywhere for free?
23. If you could add one subject to every school’s curriculum, what would it be?
24. What would you do if you could control the weather?
25. If you could own any business, what kind would it be?
26. What would you do if you found out you could teleport?
27. If you could live through any event in history, what would you pick?
28. What would you do if you could experience a day in someone else’s shoes?
29. If you could bring one historical figure back to life, who would it be?
30. What would you do if you were a superhero for a day?
31. If you could live in any TV show, what would it be?
32. What would you do if you found out you had a secret talent?
33. If you could erase one event from history, which one would you choose?
34. What would you do if you could turn invisible at will?
35. If you could adopt any one character trait instantly, what would it be?
36. What would you do if you could change one law?
37. If you could have a never-ending supply of something, what would it be?
38. What would you do if you could read minds?
39. If you could build your dream house, what would it look like?
40. What would you do if you were suddenly incredibly lucky for one day?
41. If you could hold any world record, which one would you choose?
42. What would you do if you were offered a trip to space?
43. If you could choose the perfect career for me, what would it be?
44. What would you do if you could redo any one decision in your life?
45. If you could go back and give your younger self advice, what would you say?
46. What would you do if you could stop time for 10 seconds every day?
47. If you could instantly have a Ph.D. in any subject, what would it be?
48. What would you do if you could breathe underwater?
49. If you could have any superhero powers, which would you choose?
50. What would you do if you found a doorway to another dimension in your house?

To Ask a Girl

1. If you could be a famous model or a genius scientist, which would you choose?
2. What would you do if you could live as a character in a Disney movie?
3. If you could have a one-hour conversation with any fictional character, who would it be?
4. What would you do if you were trapped in a shopping mall overnight?
5. If you could instantly have any hairstyle, what would it look like?
6. What would you do if you could swap lives with your best friend for a day?
7. If you could travel anywhere in time just to witness an event, when and where would you go?
8. What would you do if you were a contestant on a singing show but couldn’t sing?
9. If you could write a letter to your 10-year-old self, what advice would you give?
10. What would you do if you could make one of your guilty pleasures healthy?
11. If you had to dress in one color for the rest of your life, which color would you pick?
12. What would you do if you were granted the ability to change one law?
13. If you could gift yourself any one item, regardless of cost, what would it be?
14. What would you do if you had the power to heal broken hearts?
15. If you could instantly acquire a new hobby and be good at it, what would it be?
16. What would you do if you woke up as a character in your favorite book?
17. If you could instantly change your profession, what job would you want to do?
18. What would you do if you could choose any animal as a pet, and it would be perfectly trained?
19. If you could turn any activity into an Olympic sport, what would it be?
20. What would you do if you found out you were a princess of a small country?
21. If you could live in any era of fashion history, when would you choose?
22. What would you do if you could have dinner with any fictional villain?
23. If you could change the ending of any movie, which one would it be?
24. What would you do if you had a magical mirror that always told the truth?
25. If you had to live in a famous painting, which one would you choose?
26. What would you do if you could see one year into your future?
27. If you could be any element (water, fire, earth, air), which one would you be?
28. What would you do if you could control electronics with your mind?
29. If you could make a 30-second speech to the whole world, what would you say?
30. What would you do if you had a pet dragon for a day?
31. If you could be a guest star on any TV show, which one would you pick?
32. What would you do if you were granted the ability to talk to plants?
33. If you could choose any two fictional characters to be your parents, who would they be?
34. What would you do if you found a book where anything you wrote in it became true?
35. If you could give one piece of advice to everyone in the world, what would it be?
36. What would you do if you could instantly learn any dance style?
37. If you could get a lifetime supply of any makeup item, what would it be?
38. What would you do if you had a clone for a day?
39. If you had to live in a universe from any video game, which would you choose?
40. What would you do if you could have a playlist of background music for your life?
41. If you could instantly have a full wardrobe of any style, what style would you choose?
42. What would you do if you had to survive a zombie apocalypse?
43. If you could design your dream pair of shoes, what would they look like?
44. What would you do if you could be a judge on a talent show?
45. If you could ban one type of junk food forever, what would it be?
46. What would you do if you could have the perfect Instagram feed?
47. If you could live in a house made of any material, what would it be?
48. What would you do if you could walk on clouds?
49. If you could have the last text you sent come true, what would it be?
50. What would you do if you could switch lives with any historical figure?

Funny Hypothetical Questions

1. If you could only talk in song lyrics for the rest of your life, how would you communicate?
2. What would you do if you had to eat a bowl of cereal with soda instead of milk?
3. If you were a wrestler, what would your entrance theme song be?
4. What would you do if your life had a laugh track that only you could hear?
5. If you had to replace your hands with objects already in your house, what would you pick?
6. What would you do if you found out your life was a reality TV show?
7. If you were a potato, how would you like to be cooked?
8. What would you do if you could only move forward by doing the moonwalk?
9. If you had to pick a new first name, but it had to be a food item, what would it be?
10. What would you do if you could only laugh like a villain in a cartoon?
11. If you had to turn into a Disney sidekick, who would you choose?
12. What would you do if you woke up and you were the star of an infomercial?
13. If you could replace rain with any liquid, what would it be?
14. What would you do if you had a 10-second dance party every time you heard a doorbell?
15. If you had to enter rooms like a sitcom character, what would your catchphrase be?
16. What would you do if your life had background music that everyone could hear?
17. If you could add a word to the dictionary, what would it be, and what’s its definition?
18. What would you do if you could only communicate through interpretive dance?
19. If you had to be a piece of furniture, what would you be?
20. What would you do if your clothes randomly changed color based on your mood?
21. If you had to pick a fruit to fight with in a food fight, what would it be?
22. What would you do if you had to use spaghetti as shoelaces?
23. If you could only eat one condiment for the rest of your life, which would you choose?
24. What would you do if you had to speak like Shakespeare for a day?
25. If you were a smell, what smell would you be?
26. What would you do if you could only talk like a pirate?
27. If you had to greet everyone by yodeling, how would your social life change?
28. What would you do if you had to sneeze glitter?
29. If your legs were replaced with pogo sticks, how would you get around?
30. What would you do if your pet could suddenly talk?
31. If you had to battle a giant chicken, what would be your weapon of choice?
32. What would you do if you could only shop for clothes at a costume store?
33. If you were a sandwich, what kind of sandwich would you be?
34. What would you do if you could only use pick-up lines to start conversations?
35. If you could only use one emoji for the rest of your life, which one would it be?
36. What would you do if you could only eat food that rhymes with your name?
37. If you were a kitchen appliance, which one would you be?
38. What would you do if you woke up as a character in a video game?
39. If you were a tree, what kind of tree would you be and why?
40. What would you do if your alarm clock played circus music to wake you up?
41. If you could only high-five people to greet them, would you still have friends?
42. What would you do if you could only whisper or shout?
43. If you were a hashtag, what would you be?
44. What would you do if you had to replace all drinks with coffee or tea?
45. If you were a superhero, what would your useless superpower be?
46. What would you do if you had to give up one color forever?
47. If you were a crayon, what would your color and name be?
48. What would you do if you had to win a dance-off to save the world?
49. If you had a band, what would you name it?
50. What would you do if you had to enter a hotdog eating contest against a robot?

Deep Hypothetical Questions

1. If you could go back in time to prevent one event, what would it be?
2. What would you do if you had to choose between saving a loved one or saving 100 strangers?
3. If you found out you were living in a simulation, how would it change how you live your life?
4. What would you do if you discovered the secret to eternal life?
5. If you had to sacrifice personal freedom for the greater good, which would you choose?
6. What would you do if you had the power to eliminate one human emotion from existence?
7. If you had to live your life without one of your five senses, which would you give up?
8. What would you do if you had only one day left to live?
9. If you could go back in time and change one personal decision, what would it be?
10. What would you do if you were given the responsibility to govern a new planet?
11. If you could fully understand one unsolved mystery, which would it be?
12. What would you do if you had the ability to read minds, but couldn’t turn it off?
13. If you could see the outcome of every choice you make, would you want to?
14. What would you do if you were offered the chance to know the exact time and place of your death?
15. If you had to relive one year of your life forever, which year would it be?
16. What would you do if you had to choose between love and success?
17. If you could resolve one global issue, what would it be?
18. What would you do if you could experience someone else’s life for a day?
19. If you could relive one moment in your life without changing anything, what would it be?
20. What would you do if you could bring back one person from the dead?
21. If you could take on the pain of anyone in the world, would you?
22. What would you do if you found out everything you believed was a lie?
23. If you had to erase one memory, what would it be?
24. What would you do if you had to live your life without feeling any physical pain?
25. If you could take back one thing you’ve said in your life, what would it be?
26. What would you do if you had the power to change one event in history?
27. If you could instantly gain any one skill, what would it be and why?
28. What would you do if you found a way to make peace among all nations?
29. If you had to live in a world without art or science, which would you choose?
30. What would you do if you found out you were destined for something extraordinary?
31. If you could erase one thing from existence, what would it be?
32. What would you do if you had to live your life over, but could keep your current knowledge?
33. If you could permanently change one law of nature, what would it be?
34. What would you do if you could visit any time period, but not return?
35. If you could experience the life of one famous person, who would you pick?
36. What would you do if you were the last person on Earth?
37. If you could know the answer to any unsolved question, what would it be?
38. What would you do if you could change one aspect of human nature?
39. If you had to choose between truth without happiness or happiness without truth, which would you choose?
40. What would you do if you could communicate with an alternate version of yourself?
41. If you could meet God, what one question would you ask?
42. What would you do if you had the ability to cure one disease?
43. If you were given the chance to restart civilization, what would you do differently?
44. What would you do if you could instantly learn one language?
45. If you could have witnessed any event in history, what would it be?
46. What would you do if you had the ability to control time?
47. If you had to relive the same day over and over, how would you spend it?
48. What would you do if you had the power to make everyone happy but yourself?
49. If you could be guaranteed one answer to any question, what would you ask?
50. What would you do if you found out that our reality was just one of many?

Frequently Asked Questions

How do hypothetical questions aid in self-reflection?

Asking yourself hypothetical questions can be a powerful tool for self-reflection. Questions like, “What would I do if I weren’t afraid?” can help you identify fears, dreams, or areas of your life that might need change.

Are hypothetical questions good for group discussions?

Absolutely. In group settings, these questions can serve as ice-breakers or ways to liven up the discussion. Just be sure the questions are appropriate for the audience.

What should I avoid when asking hypothetical questions?

When asking hypothetical questions, avoid:

• Sensitive Topics: Such as trauma or deeply personal issues, unless you’re sure the other person is comfortable discussing them.
• Overly Complex Scenarios: Keep it simple so that the conversation flows easily.
• Rapid-Fire Questioning: Give the other person time to think and respond.