Have you ever found yourself drawn into or involved in a situation where an awkward conversation transpires? Or have you ever struggled to initiate or continue a conversation because you’re not sure what to say? We know just how nerve-racking and challenging it can be to think up questions to ask your friends, family, co-workers, or a date. 

Fortunately, one of the very best ways to get out of an awkward conversation or get to know someone better is with a tried and trusted conversation game of “Would You Rather.” You would be genuinely surprised by the incredible amount you can learn about someone or how quickly you can rescue a tremulous situation by playing this simple question game. 

Additionally, a game of Would You Rather questions doesn’t have to be deep or intellectually stimulating. Many questions touch on different topics, but not all of them are thought proving or emotionally revealing. 

After reading through the thousands of Would You Rather questions, we have assembled a list comprising only the best of the best. You will notice that we have included funny, risky, thought-provoking, and many other categories of Would You Rather questions to present you with a well-rounded list. 

All you have to do is pick out a few of these and use them the next time you participate or initiate a conversation where you’re unsure what to say. 

The 101 Best Would You Rather Questions of All Time

1. Would you rather be subjected to listening to the exact same song for the rest of your life or have to watch the same movie on repeat for the rest of your life?
2. Would you rather have a personal time machine that could take you back to the past or a teleporter that could only take you somewhere in the present?
3. Would you rather speak in rhymes or riddles for the rest of your life?
4. Would you rather be immortal with super strength or live an average human lifespan but wake up with a new superpower each day?
5. Would you rather be stranded on a completely isolated tropical island alone with enough food for a month or be stranded with a friend with only enough food to last a week?
6. Would you rather be a ruler living in the middle ages or an ordinary person living in the future?
7. Would you rather have no voice when someone asks you a question or only be able to laugh when someone cries?
8. Would you rather have everything you have ever wanted or be liked by anyone you ever meet?
9. Would you rather be immortal with limited money or have unlimited money but a human lifespan?
10. Would you rather relinquish all takeaways for a year or go without your smartphone for a month?
11. Would you rather get a visible face tattoo of your choice or get a tattoo in a discrete area chosen by someone else?
12. Would you rather be incredibly intelligent or be brilliant at any sport you tried?
13. Would you rather completely lose your ability to speak for 10 years or lose your ability to hear for 10 years?
14. Would you rather explosively sneeze every time you greet someone or have the urge to pee every time you answer a direct question?
15. Would you rather have the capability to be invisible for one hour every day or be able to fly six hours out of every day?
16. Would you rather wear clothes that are one size too small or shoes that are two sizes too big?
17. Would you rather live in an extreme real-life version of Jurassic World or live in a real-life version of The Walking Dead?
18. Would you rather witness the world beginning or the world ending?
19. Would you rather stub your pinky toe or get a paper cut?
20. Would you rather like an ancient photo of a past ex on Instagram or send a sext to your mother?
21. Would you rather get all your wisdom teeth pulled or have your entire face pierced?
22. Would you rather only speak precisely what you are thinking or never have the ability to talk again?
23. Would you rather have the psychic ability to see an hour into the future or an hour into the past?
24. Would you rather have to exclusively hunt and gather everything you eat or only eat Mcdonald’s food for the rest of your life?
25. Would you rather be an ordinary wizard and live in the Harry Potter universe but have limited powers or live in the Marvel universe and have unlimited power but be a villain?
26. Would you rather communicate solely with the dead or with any living creature?
27. Would you rather believe everything you are told or lose the ability to lie?
28. Would you rather sing along to every song you hear or dance to every song you know?
29. Would you rather find your soulmate today or win the lottery next year?
30. Would you rather converse with a dead relative or your future child?
31. Would you rather have your Netflix accounts viewing history made public or your internet search history made public?
32. Would you rather have a permanent disfigurement or a permanently lousy haircut?
33. Would you rather have your pet be able to communicate with you but not understand what they are saying or have your pet understand everything you say but not speak to you?
34. Would you rather have multiple credit cards with a $10,000 limit or have $1,000 cash but never have to pay it back?
35. Would you rather go to a dangerous prison and be in solitary confinement for five years or be in a coma for ten years?
36. Would you rather travel the globe for a year, all expenses paid, or would you rather have $50,000 that you can spend on anything?
37. Would you rather be an alien with telepathic abilities or a robot with limitless firepower?
38. Would you rather lose all your most cherished memories from your childhood or lose all the memories you have of the last year?
39. Would you rather be covered in reptilian scales or bird feathers?
40. Would you rather have your internet history available to everyone but your family or have everyone be able to read your unsavory thoughts?
41. Would you rather always be two hours early or half an hour late?
42. Would you rather know the circumstances surrounding your death or know the exact date you will die?
43. Would you rather have a long and happy life with your partner or 10 years with your celebrity crush?
44. Would you rather starve to death within a month or be a cannibal for the rest of your life?
45. Would you rather have a key that can open any door or have a real get out of prison free card that can be utilized once?
46. Would you rather be able to see years into the future or know the history of every object you touch?
47. Would you rather have to work at a job you hate for the rest of your life or have to eat every food you dislike for the rest of your life?
48. Would you rather give up the internet for a year or air conditioning and heating appliances for the rest of your life?
49. Would you rather communicate with land animals or sea creatures?
50. Would you rather live your entire adult life in a recreational vehicle or a sailboat?
51. Would you rather climb Mount Everest with an inexperienced guide or explore the Amazon with an experienced guide that doesn’t speak the same language as you?
52. Would you rather buy 10 items you don’t need every time you go shopping or forget the one thing you desperately need each time you go shopping?
53. Would you rather have x-ray vision or super-sensitive hearing?
54. Would you rather only be permitted to go out during the evening or only go out in the day?
55. Would you rather see an hour into your future or an hour into someone else’s future?
56. Would you rather have toes for fingers or fingers for toes? 
57. Would you rather touch someone and experience their darkest sin or touch someone and experience their greatest achievement.
58. Would you rather be the very first person to explore a new planet or be the person who invents a pharmaceutical drug that can cure a disease?
59. Would you rather go back to being age five with everything you know now or stay the age you are but know everything your future self learns? 
60. Would you rather have to wear a baby bib every time you go out to eat at a restaurant or have to drink from a sippy cup every time you go to a bar?
61. Would you rather lose every picture you have or lose all your money?
62. Would you rather have a perpetually slow internet connection or always get stuck in traffic?
63. Would you rather only watch movies for the rest of your life or only be able to read comic books for the rest of your life?
64. Would you rather be the judge that decides someone’s punishment or the person who has to enforce a punishment that is given?
65. Would you rather have a pause and fast forward button or a rewind button in your life?
66. Would you rather be feared by everyone you meet or loved by everyone you hate?
67. Would you rather never travel in an airplane again or never be able to use the internet again?
68. Would you rather have the unsavory ability to control humans with your mind or have the ability to control electronics with your mind?
69. Would you rather always have a limitless tank of gas when in the city or always have a full phone battery regardless of where you are?
70. Would you rather have the ability to film everything you see or record everything you hear?
71. Would you rather have a boring but meaningful life or an exciting but dangerous life?
72. Would you rather be reincarnated as a fish or as a bird?
73. Would you rather take an entire year off at the end of your life or be forced to relive the same day for a month?
74. Would you rather have unlimited travel tickets or never have to pay for the food you consume at a restaurant?
75. Would you rather never feel satisfaction or never be able to get sad?
76. Would you rather have children with a different person every 10 years or never have any children?
77. Would you rather be able to hear everything that is said about you or be able to take back anything you have said?
78. Would you rather be the very best at something you love that no one takes seriously or be average at something that is well respected?
79. Would you rather have to wear wet soggy socks every day or only be able to wash your hair once every two weeks?
80. Would you rather solve the world food crisis or climate change?
81. Would you rather find yourself lost in a dangerous city or be lost in the wilderness?
82. Would you rather give up beer for the rest of your life or give up dairy products for a year of your life?
83. Would you rather your best friend win $1 million or you win $10,000?
84. Would you rather stay the same age you are now for eternity or remain the way you are now financially until you die?
85. Would you rather never be capable of leaving the city or town you were born in or have to leave every month for a new city or town?
86. Would you rather gain one new positive habit or get rid of one of your worst habits?
87. Would you rather live a year entirely alone or live a year without a home of your own?
88. Would you rather your mother or your sibling pick your future spouse?
89. Would you rather be insane and know that you are insane or be insane but believe you are sane?
90. Would you rather alter the outcome of the future elections or change the result of a past election?
91. Would you rather be suddenly elected as a president of a country with no political knowledge or be made a CEO of a corporation with no business savvy?
92. Would you rather have all your cellphone history leaked, including texts and photos, or never be able to use your cellphone again?
93. Would you rather be late to your mother’s funeral or late to your own wedding?
94. Would you rather be able to discern when someone is lying or get away with lying every time?
95. Would you rather people knew all the gritty details about your love life or all the details about your financial status?
96. Would you rather have no thumbs and pinkies or no index fingers?
97. Would you rather be paid your salary in coins or never be paid a salary again?
98. Would you rather never use any form of social media again or never be able to watch another movie?
99. Would you rather have an analytically photographic memory or have the ability to never lose focus on a task you are busy with?
100. Would you rather have your every thought appear above your head or have your every activity live-streamed to your friends and family?
101. Would you rather have every shirt you ever wear be uncomfortably itchy or only be able to use one-ply toilet paper for the rest of your life?

See more about – Top 75 Best Manly Hobbies For Men