60+ Hypothetical Questions to Ask Your Friends, Family, or Partner

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The most hilarious "what if" questions to get to know your loved ones
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Want to liven up a dull situation? Ask a silly “what if” question to make everyone smile! Even if you think you know someone inside-out, “what if’s” build even deeper connections with your loved ones. If you need some inspiration, here are 60+ funny “what if” questions guaranteed to make your friends, family, and co-workers giggle via text or in person.

Things You Should Know

  • The funniest “what if” questions involve changing history or the future, so have fun creating weird, wacky scenarios to make everyone laugh .
  • Remember not to take yourself too seriously ; “what if’s” are a fun way to lighten the mood and keep people entertained.
  • After your initial “what if” question, ask the other person to elaborate on their answer to get to know them better.
1

The Past, Present & Future

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    What if you could time travel to any period? What if you were reborn 100 years ago? Envision a variety of different scenarios with questions like:
    • What year would you travel to and why?
    • What if you could eliminate one historical event? Which would you choose and why?
    • What would your occupation be if you lived 100 years ago?
    • What if you could un-invent something? What item would you choose and why?
    • What if you were president of the US for one day? What would you do?
    • What if you woke up tomorrow and your entire life was a dream? What would you do?
    • What if social media didn’t exist? How would things be different?
    • What if you could stop time for one year? What would you do and why?
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2

TV, Music & Movies

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    Nothing connects us all quite like movies, TV shows, and music—so what better way is there to break the ice than by jumping into one of these topics? Get the convo going with Qs like:
    • What if you could only listen to one artist for the rest of your life? Who would you pick and why?
    • What if you could only watch one movie for the rest of your life? What movie would you watch and why?
    • What if you got to guest star on any TV show? What show would you pick and why?
    • What if you had to room with 5 fictional characters? Who would they be and why?
    • What if you could live in any fictional world? Which would you choose and why?
    • What if you could make a kid’s TV show? What would it be about?
    • What if you could make a band with any 5 solo artists, dead or alive? Who would they be and why?
3

Goofy Scenarios

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    What if you woke up one morning and your legs were hot dogs? What if you could rename one inanimate object? Invite the other person to take a closer (and sillier) look at the world around them with Qs like:
    • What if someone followed you around and narrated your life? Who would you want it to be?
    • What if we hosted a comedy roast? What would you say about me?
    • What if the floor was lava? How would you get from place to place?
    • What if it rained food? What food would you want it to be?
    • What if you found a genie in a bottle? What 3 wishes would you ask?
    • What if you were a mad scientist? What would you invent and why?
    • What if you could eliminate one word from existence? What would it be and why?
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4

Special Powers

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    The ability to time travel. The power of invincibility. It's always fun to imagine what life would be like powered up—and now you can! Try a few of these questions on for size:
    • What if everything you touched turned to chocolate? What would you do and why?
    • What if anything you drew came to life? What would you draw?
    • What if you could have any superpower? Which power would you want?
    • What if you woke up as an animal? What animal would you be and why?
    • What if you could fly? Where would you go?
    • What if you could live in space or underwater? Which would you choose and why?
    • What if you could only see one color? What color would you choose and why?
    • What if aliens invaded Earth? What would you do?
5

Kid-Friendly Questions

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    Run out of stuff to do while hanging out with your pals? Chase the boredom away with a variety of fun "what if" scenarios, like:
    • What if your parents said yes to everything for one day? What would you do?
    • What if you could have an unlimited supply of one thing for the rest of your life? What would you choose and why?
    • What if your favorite video game didn’t exist? What would you do in your free time instead?
    • What if homework didn’t exist? What would you do if you had more free time?
    • What if you were the only person in the world? What would you do?
    • What if all of your toys could talk? What would you say to them?
    • What if you were an adult for a day? What would you do?
    • What if you could get rid of one vegetable forever? What would you choose?
    • What if you could travel to Mars? Would you go?
    • What if you won $1,000,000? What would you do with the money?
    • What if you could meet any famous person? Who would you meet and why?
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6

Funny Romantic Questions

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    What if we had our own reality TV show? What if we made up our own language? Encourage them to dig deep and really think outside of the box with questions like:
    • What if we replaced the lead characters in a movie? Who would we be and why?
    • What if we could throw a party with an unlimited budget? What would it look like?
    • What if we could only watch one streaming service for the rest of our lives? Which service would you choose and why?
    • What if your 10-year-old self wrote your dating profile? What would it say?
    • What if you could date any celebrity? Who would it be?
    • What if we could move to any country? Which would you choose and why?
    • What if I bought a pet without asking you? How would you react?
    • What if we lived in the Stone Age? Do you think we could survive?
7

Serious Romantic Questions

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    What if we could have 10 kids or no kids? What if we had to switch jobs for a day? Dive into some more serious what-if scenarios and see what your partner says:
    • What if you could build your dream home? What would it look like?
    • What if you could relive any memory? Which memory would you choose and why?
    • What if you found out a loved one committed a terrible crime? What would you do?
    • What if you had the ability to change one thing about your life? What would you change and why?
    • What if we had met earlier? How would things be different?
    • What if we went on your dream date? What would it look like?
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