134 Best Deep Yes or No Questions To Ask (2024)

If you’re looking for great Yes or No questions to ask one of your friends or even a complete stranger, you’re in the right place.

Yes or No questions are a simple way to get to know people on a deeper level. 

In fact, I have curated this list of 134 Yes Or No questions to be as useful for doing that as possible.

So, let’s dive in.  

Yes or No Questions To Ask
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What Is A Good Yes or No Question To Ask?

A good Yes or No question should have the possibility of a funny, outrageous or surprising  answer. Ideally, if the answer is yes, you would be desperate to start a conversation to learn more. 

Let’s illustrate with some example questions. “Have you ever been arrested?” is a question that is likely to shock people if the answer is ‘Yes’, because most people never get arrested in their life.

An example of boring or random Yes Or No questions? “Have you ever made your own bread to eat?”, “Have you ever eaten cauliflower?” or “Have you ever seen Game Of Thrones?” These questions are boring because it’s not too funny, outrageous or surprising if they have or haven’t. Don’t ask Yes Or No questions if the answers aren’t going to be funny, surprising or exciting. 

Most likely, you don’t care whether your best friend did ever eat cauliflower or not. You surely  won’t want to hear a more detailed story of that time they did eat it. That probably won’t be a fun answer.  

You’re looking for drama!! Have they done something naughty? Have they done something crazy? Have they ever been through some hard times? You should be using Yes Or No questions to search for highlights from their life. Not boring day-to-day occurrences.   

You could also use Yes Or No Questions as a way of getting their opinions on deep subjects or moral dilemmas. Do you believe in aliens? Would you ever cheat on a partner? These are two examples of tricky Yes Or No Questions that would do this. Indeed, tricky Yes Or No Questions like this can often inspire the deepest conversations.  

How To Ask Yes Or No Questions

Most people overthink this.

A lot of men especially will only want to ask a question if it makes logical sense in the context of a conversation.

That’s so unnecessary. If the question is funny, interesting or entertaining, there’s no reason why a friend or partner wouldn’t want to answer it, even if it seems a bit random. 

With that said, there’s nothing wrong with asking someone if they want to play a ‘Yes Or No Questions’ game to get to know each other better.

In this game, you’d take turns answering Yes Or No questions. Of course, if they give an answer that’s interesting, do invite them to elaborate on the story of what happened. The reason you play the game is to get to know each other better, after all.   

A great thing about the Yes Or No questions games is that you might end up getting to know yourself better as well.

134 Deep Yes Or No Questions

  1. Have you ever broken someone’s heart?
  2. Have you ever caught someone cheating on their boyfriend or girlfriend?
  3. Do you think that a man and a woman can be exclusively friends?
  4. Have you ever fainted from drinking so much?
  5. Have you ever found something so funny you couldn’t stop laughing?
  6. Have you ever had a crush on a teacher?
  7. If you were invited to go to Mars, would you go?
  8. Do you consider yourself a controversial person?
  9. Have you ever broken someone’s property and not told them?
  10. Have you ever played a game of strip poker?
  11. Do you have any regrets?
  12. Would you travel the world solo?
  13. Do you think men and women are equal?
  14. Have you ever flirted with someone you didn’t like for attention?
  15. Ever had feelings for someone who didn’t have them back?
  16. Have you ever fallen asleep at school or work?
  17. Have you ever slept with a complete stranger?
  18. Have you ever gone more than a year without sex, as an adult?
  19. Have you ever witnessed a crime?
  20. Are you a feminist?
  21. Have you ever gone more than 24 hours without eating?
  22. Do you easily forgive people?
  23. Have you ever been cheated on by a boyfriend or girlfriend?
  24. Have you ever been unfaithful?
  25. Have you ever run away from your problems?
  26. Have you even been humiliated in front of your crush?
  27. Would you let me see your WhatsApp conversations?
  28. Have you had a crush on anyone in this room?
  29. Have you ever been kissed in the rain?
  30. Have you ever seen someone die?
  31. Would you let me see your Google search history?
  32. Have you ever fallen in love?
  33. Have you ever been drunk when you shouldn’t have been?
  34. Have you ever judged someone for a secret that I told you?
  35. Would you ever watch adult movies with your boyfriend or girlfriend?
  36. Have you ever passed out in a public place?
  37. Have you ever faked an orgasm?
  38. Have you ever experienced a natural disaster?
  39. Have you ever played a game of spin the bottle?
  40. Do you think that white lies are justifiable?
  41. Have you ever finished someone with a text message?
  42. Is money a decisive factor when choosing your partners?
  43. Would you be in a poly love relationship?
  44. Would you return to someone who has been unfaithful to you?
  45. Are you happy studying what you are studying or working on what you are working on?
  46. Would you kiss someone inside your circle of friends?
  47. Do you think confessions are a way to strengthen relationships?
  48. Have you ever seen your best friend naked?
  49. Have you ever sent nudes?
  50. Have you ever kissed a picture?
  51. Have you ever fallen in love with a stranger?
  52. Have you ever failed a class that you needed to pass?
  53. Have you ever felt like killing someone?
  54. Would you sleep with a person of the same sex?
  55. Have you gotten away with something truly terrible?
  56. Would you be happy if you died tomorrow?
  57. Is it possible to love a partner more than your family?
  58. Do you consider yourself funny?
  59. Are you religious?
  60. Do you trust people easily?
  61. Have you ever made either of your parents cry?
  62. Would you ever have a friend with benefits?
  63. Do you usually follow your brain more than the heart?
  64. Do you want to have children?
  65. Do you know why you wake up everyday?
  66. Have you ever been in a fight?
  67. Would you ever have a one-night stand?
  68. Could you ever forgive an infidelity?
  69. Have you ever dated someone your parents hated?
  70. Do you still have contact with your childhood friends?
  71. Do you have a dirty secret that no-one knows?
  72. Would you like to know when you’re going to die?
  73. Have you ever liked a neighbor?
  74. Is there someone in this world you love more than anyone else?
  75. Has your heart ever been broken?
  76. Do you consider yourself superior to others?
  77. Are you scared to die?
  78. Have you ever cried watching a film?
  79. Are you friends with any of your exes?
  80. Would you ever live in another country?
  81. Have you ever bullied someone?
  82. Have you ever been harassed by an ex?
  83. Are you doing what you always wanted to do in your life?
  84. Have you ever doubted your sexuality?
  85. Have you had a near-death experience?
  86. Do you get along with your parents?
  87. Have your parents caught you in an intimate moment?
  88. Have you ever dreamt of sleeping with someone else?
  89. Have your parents caught you telling a huge lie?
  90. Have you ever considered deleting yoru social media?
  91. Would you get involved in an open relationship?
  92. Have you ever lost someone close?
  93. Have you ever been so scared you called a friend for help?
  94. Would you relive your school years if you could?
  95. Do people usually get the wrong impression of you?
  96. Have you ever cried because of something completely ridiculous?
  97. Do you consider yourself a spiritual person?
  98. Have you ever felt like dying?
  99. Have you ever tried drugs?
  100. Have you ever spread a false rumor about someone?
  101. Would you ever go back to an ex?
  102. Have you ever snuck into somewhere forbidden?
  103. If you won the lottery, would you tell your family and friends?
  104. Are any of your friends as important to you as your family?
  105. Have you ever been skinny dipping?
  106. Would you ever tattoo someone’s name on you?
  107. Do you believe in life after death?
  108. Have you ever stolen money, or something valuable?
  109. Have you ever swam naked?
  110. Do you believe in ghosts or aliens?
  111. Have you ever slept with someone and immediately regretted it?
  112. Is social class important when choosing your partner?
  113. Would you be able to forgive the betrayal of a friend?
  114. Would you ever have a threesome with your boyfriend or girlfriend?
  115. Have you ever had feelings for your best friends?
  116. Have you fallen in love at first sight?
  117. Have you ever forgotten an anniversary or an important date?
  118. Have you ever had a crush on someone inappropriate?
  119. Have you ever cheated on a partner?
  120. Have you ever written someone a love poem?
  121. Have you ever caught someone breaking the law?
  122. Have you ever slept with two different people in one day?
  123. Do you think people can change?
  124. Is this the best time in history to be alive?
  125. Do you know how to play at least one musical instrument?
  126. Have you ever loved someone you shouldn’t?
  127. Have you embarrassed yourself in front of your whole class?
  128. Have you ever played hookie from school or work to do something awesome?
  129. Have you ever kissed someone in this room?
  130. Would you ever consider changing your identity?
  131. Would you be with someone whose relgious beliefs are different to yours?
  132. Have you ever been in trouble with the police?
  133. Would you sleep with someone for money?
  134. Do you want to get married one day?

Related: 121+ Let’s Get Deep Questions For Couples To Connect Again

Are You Looking For More Yes Or No Questions To Ask?

I hope you enjoyed my list of Yes Or No Questions.

If you want to add your own favorite Yes Or No Questions, you can do so in the comments section below.

If you’re looking for more funny or random Yes Or No Questions to ask people, feel free to see what questions have already been added to the comments section. Maybe you want to answer Yes or No to these questions yourself! 

Thanks for reading!

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About The Author

Bijan Kholghi is a certified life coach with the Milton Erickson Institute Heidelberg (Germany). He helps clients and couples reach breakthroughs in their lives by changing subconscious patterns. His solution-oriented approach is based on Systemic- and Hypnotherapy.