Best Deep Would You Rather questions. Each one is simple and to the point. We’ve grouped them by topic – personal challenges, school dilemmas, work choices, adult realities – so you can find the ones that resonate with you.
Take your time and read every question on this page. Each one is designed to make you stop, think, and engage fully. Stay with us as you work through these questions and let your mind go with each scenario. Have fun! For more exciting dilemmas, check out our Crazy Would You Rather Questions list!
❔99 Best Deep Would You Rather Questions For Every Mood
Deep Questions
❔1. 🤔 Would you rather lose all memories of your childhood or forget the last five years?
❔2. 🤔 Would you rather know how you die or when you die?
❔3. 🤔 Would you rather live in a world without lies or a world without secrets?
❔4. 🤔 Would you rather permanently lose the ability to speak or to write?
❔5. 🤔 Would you rather erase your biggest regret or relive your happiest moment once?
School/Education
❔6. 🎓 Would you rather attend school for 12 hours a day but only three days a week or eight hours a day for six days?
❔7. 🎓 Would you rather fail a class everyone aced or be suspected of cheating on a test you aced?
❔8. 🎓 Would you rather have a teacher who grades unfairly but teaches well or one who’s kind but unqualified?
❔9. 🎓 Would you rather lose your entire semester’s work or have it leaked publicly?
❔10. 🎓 Would you rather defend a friend caught plagiarizing or report them anonymously?
Work/Career
❔11. 💼 Would you rather work for a toxic boss with a high salary or a kind boss with low pay?
❔12. 💼 Would you rather take credit for a coworker’s idea or let them take credit for yours?
❔13. 💼 Would you rather lose your job but keep your reputation or keep your job but ruin your reputation?
❔14. 💼 Would you rather work 80-hour weeks for a promotion or stay in your role with no advancement?
❔15. 💼 Would you rather retire at 40 with no savings or work until 70 with financial security?
Friendships
❔16. 👫 Would you rather lose a friend over money or over a secret?
❔17. 👫 Would you rather have a friend who’s always late or one who cancels plans last-minute?
❔18. 👫 Would you rather your friend date someone you hate or you date someone they hate?
❔19. 👫 Would you rather confront a friend about their harmful habit or cut them off silently?
❔20. 👫 Would you rather keep a friend’s betrayal secret or expose it and lose them?
Adults/Life Choices
❔21. 🧳 Would you rather raise a child alone or stay in a loveless marriage for their sake?
❔22. 🧳 Would you rather never travel again or never see your family again?
❔23. 🧳 Would you rather lose your home but keep your job or lose your job but keep your home?
❔24. 🧳 Would you rather live with chronic pain or chronic fatigue?
❔25. 🧳 Would you rather outlive your spouse or have them outlive you?
Relationships
❔26. ❤️ Would you rather date someone jealous but loyal or trusting but distant?
❔27. ❤️ Would you rather your partner forget your anniversary or your birthday?
❔28. ❤️ Would you rather discover your partner lied about their past or their present?
❔29. ❤️ Would you rather have a passionate but unstable relationship or a boring but secure one?
❔30. ❤️ Would you rather be cheated on emotionally or physically?
Ethics/Morality
❔31. ⚖️ Would you rather steal to feed your family or let them go hungry?
❔32. ⚖️ Would you rather expose a friend’s crime or help them hide it?
❔33. ⚖️ Would you rather save a stranger’s life or your pet’s life?
❔34. ⚖️ Would you rather lie to protect someone’s feelings or tell the truth and hurt them?
❔35. ⚖️ Would you rather let a guilty person go free or jail an innocent person?
Health/Survival
❔36. 🏥 Would you rather lose your legs or your hands?
❔37. 🏥 Would you rather live with extreme claustrophobia or crippling vertigo?
❔38. 🏥 Would you rather never taste food again or never feel physical touch again?
❔39. 🏥 Would you rather survive a natural disaster alone or with strangers?
❔40. 🏥 Would you rather endure extreme heat or extreme cold forever?
Technology
❔41. 📱 Would you rather lose access to the internet or electricity for a year?
❔42. 📱 Would you rather have a camera recording your home 24/7 or your phone tracking your location?
❔43. 📱 Would you rather delete all your social media accounts or your email permanently?
❔44. 📱 Would you rather have a robot replace your best friend or your job?
❔45. 📱 Would you rather read everyone’s private messages or have everyone read yours?
Money/Lifestyle
❔46. 💰 Would you rather earn minimum wage doing your dream job or $1M doing work you hate?
❔47. 💰 Would you rather lose all your savings or owe double your current debt?
❔48. 💰 Would you rather live in a mansion with no furniture or a shack with luxury items?
❔49. 💰 Would you rather never eat out again or never buy new clothes?
❔50. 💰 Would you rather inherit wealth with strings attached or stay poor but independent?
Hypothetical Scenarios
❔51. 🌌 Would you rather speak all languages or be able to read minds?
❔52. 🌌 Would you rather be unable to cry or unable to laugh?
❔53. 🌌 Would you rather always have to shout or whisper?
❔54. 🌌 Would you rather be invisible or teleport anywhere once a day?
❔55. 🌌 Would you rather control time or manipulate reality?
Family
❔56. 👪 Would you rather your child be unhappy but successful or happy but struggling?
❔57. 👪 Would you rather disagree with your parent’s life advice or their moral values?
❔58. 👪 Would you rather raise your sibling’s children or never see them again?
❔59. 👪 Would you rather your family know everything about you or nothing at all?
❔60. 👪 Would you rather attend a family event you hate or miss a milestone moment?
Fear/Risk
❔61. 😨 Would you rather skydive with a 5% failure rate or swim with sharks unprotected?
❔62. 😨 Would you rather be trapped in a elevator for 24 hours or locked out of your home in a storm?
❔63. 😨 Would you rather face your biggest fear in real life or in a nightmare weekly?
❔64. 😨 Would you rather live in a war zone or a crime-ridden city?
❔65. 😨 Would you rather lose your sight in darkness or daylight?
Creativity
❔66. 🎨 Would you rather never create art again or never consume art again?
❔67. 🎨 Would you rather write a book everyone hates or one no one reads?
❔68. 🎨 Would you rather lose your creativity or your critical thinking skills?
❔69. 🎨 Would you rather sing publicly off-key or forget how to dance?
❔70. 🎨 Would you rather design a revolutionary product without credit or get rich copying others?
Time
❔71. ⏳ Would you rather repeat the same day for 10 years or skip ahead 10 years instantly?
❔72. ⏳ Would you rather age physically but stay mentally young or vice versa?
❔73. ⏳ Would you rather know your future or change your past?
❔74. ⏳ Would you rather live 200 years unhappily or 50 years joyfully?
❔75. ⏳ Would you rather be stuck in the past or paranoid about the future?
Identity
❔76. 🆔 Would you rather be universally disliked or forget who you are?
❔77. 🆔 Would you rather lose your name or your face?
❔78. 🆔 Would you rather be ignored in every group or mocked in every conversation?
❔79. 🆔 Would you rather be remembered for kindness or intelligence?
❔80. 🆔 Would you rather be yourself in a foreign culture or blend in but lose your identity?
Power/Control
❔81. 👑 Would you rather rule a small nation dictatorially or advise a global leader democratically?
❔82. 👑 Would you rather control the weather or control wildlife?
❔83. 👑 Would you rather have unlimited political power with no friends or be loved with no influence?
❔84. 👑 Would you rather make all decisions for your family or let others decide everything?
❔85. 👑 Would you rather be powerless in a crisis or cause the crisis unintentionally?
Nature/Environment
❔86. 🌳 Would you rather live without sunlight or without rain?
❔87. 🌳 Would you rather breathe underwater but need sunscreen 24/7 or live in space with limited oxygen?
❔88. 🌳 Would you rather all plants die or all animals go extinct?
❔89. 🌳 Would you rather endure constant earthquakes or permanent floods?
❔90. 🌳 Would you rather eat only insects or only raw meat for survival?
Final Questions
❔91. 🔚 Would you rather love someone who dies young or never love at all?
❔92. 🔚 Would you rather achieve your goals through luck or hard work?
❔93. 🔚 Would you rather speak every thought aloud or never speak again?
❔94. 🔚 Would you rather be envied or pitied?
❔95. 🔚 Would you rather lose your voice forever or have to say everything you write?
❔96. 🔚 Would you rather be stranded on an island alone or with someone you hate?
❔97. 🔚 Would you rather lose all your photos or all your keepsakes?
❔98. 🔚 Would you rather be the first to explore Mars or the ocean’s deepest trench?
❔99. 🔚 Would you rather die saving others or live knowing you didn’t try?
