50 Funny “Would You Rather…” Questions

By on November 12, 2015

1. Would you rather foretell the future, or change the past?

Gives you a clue to whether people have regrets or not…or live to have regrets.

2. Would you rather wet your pants or see your mother embarrassed?

Is it better to be embarrassed yourself, or embarrassing your mom?

3. Would you rather kiss a stranger or a frog?

OK, so this one’s mainly funny…but who knows? Some people may prefer frogs!

4. Would you rather have a pet pig or a pet snake?

Will tell you if someone prefers an animal that could eat you, or one that is nice and cuddly (and intelligent!).

5. Would you rather eat a cat or a dog if starving in the jungle and it was your only option to survive?


Cruel question, but at least you find out if they’re a dog or cat person.

6. Would you rather be famous and have a scandal or two, or never be talked about in the media at all?

Will tell you how much attention they crave from strangers (possibly also how big their ego is).

7. Would you rather be happily married or earn 10 million dollars?

Will show you if they love the love or the money.

8. Would you rather get caught naked or dancing and singing wildly whilst cleaning the house? 

This will reveal what they find embarrassing in life – a bit of nudity or a bit of acting crazy.

9. Would you rather swap lives for a day with Madonna or the British Queen?

Will show you what kind of life they are most curious about, or most desire for themselves.

10. Would you rather be a famous rock singer or the next Einstein/Tesla? 

This will definitively tell you if they prefer art to science.

11. Would you rather spend all day cleaning someone’s house, or confess to your crush you like them?

Let’s see if they have some bravery, shall we?

12. Would you rather live a carefree life by the beach, surfing and having fun, or work 10 hour days to become a millionaire? 

How much drive do they have? And what do they value?

13. Would you rather create peace on Earth or become a billionaire?

Will definitively reveal their level of generosity…


14. Would you rather perform stand-up or give a talk in front of Harvard professors?

Are they happier with the geniuses, or the clowns?

15. Would you rather run away with a circus or move to another country alone where you don’t speak the language? 

Do they prefer the security of a group, or do they prefer being a loner/love a challenge?

16. Would you rather be on a reality TV show or have to reveal intimate details of your life to your mother?

Do they like to diss their dirty laundry in public, or do they prefer the scrutinizing eye of their mother?

17. Would you rather do a striptease on the next Magic Mike movie, or in a private club?

How confident are they to strip?

18. Would you rather sing karaoke on national TV or be interviewed about everything in your life on national TV?

Do they have any secrets?

19. Would you rather go out into outer space by yourself, or into the bottom of the ocean by yourself?

Earthlings versus aliens.

20. Would you rather serenade your crush outside their window, or climb up their balcony and confess your everlasting love?

For one you will find out if they believe they can sing…

21. Would you rather have a night on town with Rihanna or Miley Cyrus?

This will reveal something about their taste…and personality!

22. Would you rather marry a complete stranger for a year minimum, or know you’ll be single for the entire year? 

How brave are they when it comes to risks?

23. Would you rather climb Mount Everest or know you’ll have to give up on your dreams?

How determined are they to reach their goals? Quite revealing.

24. Would you rather do the funky chicken in the middle of a town square, or sing karaoke in the middle of the town square?

It’s between bad and worse. Unless, of course, they’re a singer…

35. Would you rather have Sarah Palin or Kanye West as you boss for a year? 

Shows their taste in entertainment…

36. Would you rather your parents, or your crush be able to read your thoughts? 

Who do they wish to protect their secrets from the most?

37. Would you rather be able to read the thoughts of your boss/employees or whom you date?

This could be strategic if they choose one, but it could also be that they feel they don’t need to read some people’s thoughts.

38. Would you rather be stranded in America or Europe for the rest of your life? 

Home is where their heart is.

39. Would you rather relive high school and get a million dollars, or spend a year as a clown and get a million dollars?

Will reveal what they really thought of high school.


40. Would you rather walk through a room filled with spiders or a room filled with snakes?

Now you will find out how to spook them!

41. Would you rather visit a haunted house all by yourself or have a dinner date with an inmate who is serving time for assault? 

What scares them?

42. Would you rather be left alone with fifteen kids for a day, or have to spend the day mediating between a democrat and a republican? 

Are they afraid of kids?

43. Would you rather have the paparazzi camp in your back yard or never be famous? 

How much do they cherish the idea of fame?

44. Would you rather have a conversation with God or your favorite celebrity? 

Check out what their values are!

45. Would you rather become a millionaire by winning the lottery or for some work you did?

Do they like to take the easy way?

46. Would you rather jump in an icy lake, or have a one hour really hot sauna?

Just goes to show if they like it hot or cold!

47. Would you rather run through the streets naked or spend a week being lectured by your mother? 

Will reveal the person’s relationship with their mother, for sure.

48. Would you rather set off on a round the world trip by yourself, or never travel outside your country? 

Will show if they have the courage to travel by themselves. This shows a lot about a person’s courage, trust in themselves and general attitude to life.

49. Would you rather have an easy nine-to-five that pays decent money, or a demanding career that pays great money? 

Are they a go-getter?

50. Would you rather partake in a naked carnival down the street, or take a cold shower every morning for a month?

Will definitively reveal how much they care about being seen naked. Are they shy, or quite the naturist?

1507760_10152392614860079_8379465670289960282_n copy 2By Maria Montgomery – Maria is a freelance writer, director and social entrepreneur. She’s also the spokesperson for The Little Angels Community Center and an avid blogger. You can find her somewhere between Cape Town, London and L.A., where you will most likely find her in the hills, looking out over the city she loves. @OhMyMontgomery

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