Deep would you rather questions
Thoughtful questions about life, love, purpose and happiness. Good for long walks, road trips and late talks.
Would you rather…
All 80 deep would you rather questions
The bar shows how the crowd voted (once a question has 25 votes).
1. Would you rather be remembered for your kindness or for your achievements?
2. Would you rather know the meaning of life or live a meaningful life without knowing?
5. Would you rather find your purpose at 20 or find it at 60 after a full life?
6. Would you rather have a few deep friendships or many fun ones?
7. Would you rather live in the moment or plan for the future?
8. Would you rather forgive someone who hurt you or be forgiven by someone you hurt?
10. Would you rather make a big difference to one person or a small difference to many?
11. Would you rather know yourself completely or know the world completely?
12. Would you rather live a quiet, peaceful life or an exciting, chaotic one?
14. Would you rather be content with what you have or always strive for more?
15. Would you rather have your parents be proud of you or be proud of yourself?
17. Would you rather leave a legacy or leave no trace but a happy life?
18. Would you rather be loved for who you are or be loved for what you do?
19. Would you rather always have hope or always have certainty?
21. Would you rather be someone’s first love or someone’s last love?
22. Would you rather grow old with your partner or grow old with your best friends?
23. Would you rather be true to yourself and alone or fit in and be surrounded by people?
24. Would you rather know when you’ll find love or know when you’ll find success?
25. Would you rather live without fear or live without regret?
26. Would you rather have one perfect year or a hundred okay ones?
27. Would you rather have your words matter or have your actions matter?
29. Would you rather have a mentor who believed in you or be that mentor for someone else?
30. Would you rather understand why people suffer or be able to ease suffering?
31. Would you rather be the person you were at 10 or the person you’ll be at 70?
32. Would you rather have one deep conversation a week or ten casual ones?
33. Would you rather be remembered by many or deeply missed by a few?
34. Would you rather live in a world with more empathy or a world with more curiosity?
35. Would you rather always know your next step or always be surprised?
37. Would you rather find home in a place or find home in a person?
38. Would you rather have courage to start or patience to finish?
39. Would you rather be honest and unpopular or kind and sometimes dishonest?
40. Would you rather learn from your mistakes or learn from other people’s?
42. Would you rather be someone’s safe place or have a safe place yourself?
43. Would you rather make your parents’ dreams come true or make your own come true?
44. Would you rather always say what you feel or always feel what you say?
45. Would you rather have more friends or have better friends?
46. Would you rather be completely free or be completely safe?
47. Would you rather spend your life helping others or spend it creating something lasting?
48. Would you rather know every answer or ask every question?
49. Would you rather be happy most days or be extremely happy a few days a year?
50. Would you rather go back to childhood for a day or see your old age for a day?
52. Would you rather have one true friend for life or a new best friend every decade?
53. Would you rather live your life again the same way or live a completely different life?
54. Would you rather know your strengths or know your weaknesses?
56. Would you rather find love online or find love by chance in real life?
57. Would you rather make peace with the past or look forward to the future?
58. Would you rather be known for your work or be known for your character?
59. Would you rather have a slow life by the sea or a fast life in the city?
60. Would you rather always be learning or always be teaching?
61. Would you rather have a perfect memory or a perfect imagination?
62. Would you rather be someone people look up to or someone people lean on?
63. Would you rather let go of your past or stop worrying about your future?
64. Would you rather be loved by your pet or be loved by a stranger who saw your kindness?
65. Would you rather write your own story or have someone else write it?
67. Would you rather be calm in every storm or be the one who changes the weather?
68. Would you rather know the truth that hurts or believe the lie that comforts?
70. Would you rather spend more time with family or more time on your passions?
71. Would you rather live one day as someone you admire or one day as someone who admires you?
72. Would you rather give your younger self advice or get advice from your older self?
74. Would you rather feel everything deeply or feel things lightly?
75. Would you rather find meaning in work or find meaning outside work?
76. Would you rather have no enemies or have a rival who makes you better?
77. Would you rather be the light in someone’s life or have someone be yours?
78. Would you rather have a simple happy life or a complicated meaningful life?
80. Would you rather know you made a difference or never know but feel at peace?