99 Of The Best Would You Rather Questions

Looking for ways to better understand the people you care about?

Or would you like to get a quick but accurate sense of someone’s character on the first date?

It’s when people are pushed against the wall that you get to see who they really are.

But since you can’t really do that on a date without getting arrested or punched, why not try this collection of the best Would You Rather questions instead?

So much safer — and still educational!

For each of these Would You Rathers (which are meant to be difficult), you’ll present one of the following choices:

  • Two horrific or embarrassing experiences (that you’d probably never live down)
  • Two experiences you would love but have to choose between
  • Two sacrifices that would rip you in half (but only figuratively).

So, let the fun begin!

99 Best Would You Rather Questions

First dates aren’t the only scenarios where these questions will come in handy. Use them in any of the following situations:

  • Date night with your spouse or partner
  • A friendly gathering with a mix of friends and new acquaintances
  • A friendly co-worker gathering
  • A family get-together or game night

The aim here is to get to know each other and to have fun with it. There can be light-hearted teasing, but no shaming or judging allowed.

Good Would You Rather Questions

Whether you want to keep it light or level up your understanding of how each other’s minds work, you’ll find some goodies here.

1. Win a $100 million jackpot or earn a good living doing what you love?

2. Eat something every day that tastes terrible but gives you superpowers or eat something every day that you love but that makes you useless for an hour afterward?

group of people gather around a bonfire would you rather questions

3. Live in a luxury, off-the-grid treehouse overlooking a secluded beach or live in a luxe, subterranean bunker with excellent wi-fi?

4. Wear uncomfortable and unflattering clothes for the rest of your life or give up sex?

5. Have a mental connection with your soulmate / best friend — or with your most dangerous enemy?

6. See your soulmate in your dreams every night but never meet him/her in person — or be married to your soulmate but have terrible nightmares at least once a week?

7. Stop physically aging at 30 and live to 100 — or stay mentally sharp all your life but age prematurely?

8. Never have to shower or never have to sleep?

9. Live in a palatial home that always smells bad or a tiny house or apartment that always smells either soothing or energizing?

10. Have a New York apartment but be able to travel and live in different places for a time — or live in your dream home in an idyllic location for the rest of your life?

11. Have a live-in housekeeper or a live-in personal chef?


Related: 59 Of The Best Never Have I Ever Questions


12. Easily make friends with the most powerful people on earth — or have a lifelong, passionate love relationship with your soulmate?

13. Meet your soulmate when you’re both still young enough to have children together or when you’ve both lived long enough to know what you want?

14. Be colorblind or lose your sense of taste?

15. Go out for dinner with someone you’re attracted to but hardly know or with someone you know and like but aren’t attracted to?

16. Lose all your teeth or have terrible acne for a year?

17. Meet your soulmate while you’re married to someone else — or marry your soulmate only to lose him/her to a terrible accident?

18. Become a fantastic cook or a talented musician?

19. Be able to think clearly in a crisis or have an unerring sense of direction?

20. Have perfect eyesight but crooked teeth or poor eyesight but perfect teeth?

21. Live within smelling distance of a large dairy or live in a pristine, new development with a micromanaging association?

22. Win a daily coffee (any size and any type) at your favorite coffee place — or win a daily health supplement that keeps you healthy and mentally sharp?

23. Win a weekly delivery of fresh flowers (your choice or a mystery bouquet) or a weekly delivery of wine or beer (also your choice)?

24. Lose your home to a fire or get fired from your job?

25. Become a famous actor and work alongside your favorite Hollywood crush — or become the writer whose book is turned into the best movie of all time?

Hard Would You Rather Questions

The hardest Would You Rather questions are more likely to get “I don’t know” as a response. Push a little harder, though, and you’ll learn something — not just from the answer itself but also from its delivery.

26. Get a three-month vacation every year or a week-long vacation every month?

27. Marry your soulmate but earn just enough to get by — or marry a platonic friend and be rich?

28. Solve the biggest problems facing humanity but live and die alone — or live a hidden life with a deeply satisfying love relationship and meaningful work?

29. Lose your looks in a disfiguring accident or suffer brain damage that alters your personality?

30. Lose your eyesight or lose your hearing?

31. Lose your closest friend or find out you have less than a year to live?

32. Become a digital nomad who can travel the world but is dependent on the internet for survival — or become a skilled craftsman who earns enough to live decently off the grid?

33. Run a restaurant of your own at the location of your choice — or make your living by reviewing restaurants around the country and tasting the best they have to offer?

women toasting with their wine glasses would you rather questions

34. Take a supplement that makes you super-smart but always hungry – or one that keeps you slim and energetic but makes it hard to think?

35. Have hair that looks great all the time or look as though you’re wearing perfectly-applied make-up even when you’re not wearing any?

36. Have to take a medication that causes you to gain weight or one that makes you incontinent?


Related: 50 Best Friend Tag Questions And How to Play


37. Give up social media for a year or give up your favorite beverage (coffee, tea, beer, wine, etc.)?

38. Find a supplement that makes you look and smell good all the time or one that gives you super strength and speed?

39. Find $100 in a public toilet or $10 in your own pocket?

40. Know when you’ll die — or know how you’ll die?

41. Find a way to provide unlimited clean water to those who need it or find a way to purify the air all over the planet?

42. Leave Earth to join a new colony on a different planet, or live beneath Earth’s surface in a subterranean city?

43. Have unlimited battery power for your phone (no charging) or unlimited gasoline in your car (no refueling)?

44. Lose your sex drive or lose your sense of taste?

45. Go into massive debt for the experience of a lifetime or live debt free but never experience anything beyond your daily routine?

46. Always get a green light or always have lightning-fast internet?

47. Never use social media again or never watch another movie?

48. All the chats on your phone became public — or all the pictures?

49. Have a lazy eye that wanders every time you meet someone new or have a complexion that turns bright red whenever anyone talks to you?

50. Be a well-loved storyteller or a gifted magician?

Deep Would You Rather Questions

These questions go a little deeper to explore the inner workings of each other’s minds — your values, your fears, and your hidden desires.

51. Watch your loved ones die or make them watch while you destroy yourself?

52. Be blind or unable to speak?

53. Wake up as a child again or wake up very old?

54. Live with boring people who are super-positive all the time or with interesting people who complain all the time?

55. Catch one of your parents cheating on the other — or catch your significant other (SO) cheating on you?

56. Your SO could read your mind or see through your clothes?

57. Find your life’s passion — or find your soulmate?

58. Be able to shower only once a month or have painfully slow internet all the time?

59. Lose your most precious memories or live in a perpetually dirty and cluttered home?

60. Put an end to hunger or put an end to war all over the world?

61. Go camping with your soulmate or go to a luxury resort with a platonic friend?

62. Have one wish granted today or one on the day you die?

63. Have just one pair of shoes or one outfit that never wears out?


Related: 100 Intriguing Questions To Ask Your Best Friend


64. Hurt someone you love or forgive someone who hurt someone you love?

65. Live in unending summer or unending winter?

66. Lose all your money or lose all your memories?

67. Be famous and wealthy but unattached — or have a fantastic love life and obscure but meaningful work?

68. Be loved and respected by family but hated by the general public — or adored by the public but rejected by your family?

69. Be famous in this life but forgotten after you die — or be unknown while you live but famous after you die?

70. Continue with your current life as it is — or start your life over again?

71. Put an end to all wars for 100 years — or enjoy domestic bliss for the rest of your life?

72. Spend the rest of your life in prison or be executed?

friends dancing together would you rather questions

73. Be smarter than most but unkind or be kinder than most but not very bright?

74. Become poor by helping people or become rich by taking advantage of people?

75. Have an easy job working for someone else or work incredibly hard for yourself?

Crazy and Impossible Would You Rather Questions

No list of this kind would be complete without some crazy Would You Rather questions to lighten the mood a bit and excite the imagination.

76. Have a roommate with a pet python or live in an apartment infested with non-venomous spiders (the jumping kind)?

77. Live with a hoarder or with someone who keeps throwing away your stuff?

78. Wake up naked in the utility closet of your local high school — or show up at work in your underwear?

79. Wake up as a vampire or as a werewolf?

80. Realize you married an alien who loves you for who you are or realize you married a rich and powerful person who indulges but doesn’t love you?

81. Discover you’re actually a dragon shifter or that you’re the lone descendant of the most powerful wizard that ever lived?

82. Be able to make things happen just by writing about them — or be able to change the past by rewriting it?

83. Be able to travel through time and space or be able to stop time?

84. Be able to teleport yourself to any location or be able to instantly manifest whatever you want?

85. Wake up with the ability to tap into the collective knowledge of the universe — or learn that you’re an alien with the ability to control the minds of others?

86. Talk to and understand any animal — or be able to communicate in any language in the universe?

87. Wake up with superhuman strength or telekinetic powers?

88. Have lucid dreams where you preview violent deaths in time to stop them or lucid dreams where you hear the winning numbers for the next lottery jackpot?

89. Be able to pick up any instrument and play it like a pro — or be able to see and walk through walls?

90. Be able to read other people’s minds or be able to change their memories?

91. Have a car that never runs out of gas or needs repairs — or have a new car each year?

92. Live in a house that’s bigger on the inside — or have a purse or pockets that are bigger on the inside?

93. Dye your hair a new color each month or have no hair at all?

94. Be locked in a room with live tarantulas or eat a dead one?

95. Play the hero or the villain in a movie?


Related: 55 Of The Best First Date Questions To Ignite Great Conversation


96. Work puns into every conversation or don’t talk at all for a year?

97. Use a dirty public toilet or find an accommodating bush on the open road?

98. Talk in rhymes or always sound sarcastic?

99. Give up swear words forever or shave your entire body?

What's your favorite Would You Rather question?

Now that you have an ample new supply of Would You Rather questions, I hope you find a good use for them soon.

99 Of The Best Would You Rather Questions Click To Tweet

No telling what you’ll learn about family members, friends and new dating prospects that you didn’t know before.

Have fun getting to know each other better. Be kind, and build a stronger connection than the one you had before.

Appreciate your differences and what they bring to the relationship. At the very least, you’re learning to see things from a perspective different from your own.

And may your curiosity and sense of humor influence everything you do today.

Looking for ways to better understand the people you care about?Or would you like to get a quick but accurate sense of someone’s character on the first date?It’s when people are pushed against the wall that you get to see who they really are.But since you can’t really do that on a date without getting arrested or punched, why not try this collection of the best Would You Rather questions instead? #relationship #mindfulness #fun #questions #dating #happiness

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