Deep Would You Rather Questions

1. Would you rather Abe remembered for your kindness or Bbe remembered for your achievements?
2. Would you rather Ahave one conversation with your younger self or Bhave one conversation with your older self?
3. Would you rather Afind one purpose and keep it forever or Bfind a new purpose every decade?
4. Would you rather Akeep every friend you've ever made or Bmake a brand-new close friend every year?
5. Would you rather Afeel everything more deeply or Bfeel everything more calmly?
6. Would you rather Abe truly understood by one person or Bbe admired by thousands?
7. Would you rather Aknow what your pet thinks of you or Bknow what your parents really thought of you as a kid?
8. Would you rather Ahave a life full of adventure or Bhave a life full of deep friendships?
9. Would you rather Alive the same life again with no changes or Blive a completely different life?
10. Would you rather Aknow why you're here or Bbe at peace not knowing?
11. Would you rather Abe the one who always forgives or Bbe the one who's always forgiven?
12. Would you rather Ahave a home you never want to leave or Bhave a heart that always wants to wander?
13. Would you rather Aspend a year in quiet reflection or Bspend a year saying yes to everything?
14. Would you rather Abe loved for who you are now or Bbe loved for who you could become?
15. Would you rather Afind out what people say about you when you're not there or Bnever find out?
16. Would you rather Alet go of your biggest regret or Bkeep it and the lesson it taught you?
17. Would you rather Ahear the one thing your best friend never told you or Btell them the one thing you never said?
18. Would you rather Ahave a life that looks perfect to others or Bhave a life that feels perfect to you?
19. Would you rather Atrust too easily or Btrust too little?
20. Would you rather Aknow your life's biggest turning point in advance or Brecognize it only looking back?
21. Would you rather Aleave behind a great work of art or Bleave behind a great group of friends?
22. Would you rather Alive without ambition or Blive without contentment?
23. Would you rather Akeep a promise that costs you or Bbreak a promise to protect yourself?
24. Would you rather Abe wise or Bbe happy?
25. Would you rather Amake one stranger's life completely better or Bmake a thousand strangers' days a little better?
26. Would you rather Afeel at home anywhere or Bhave one place that feels like home forever?
27. Would you rather Aalways see the best in people or Balways see people exactly as they are?
28. Would you rather Aspend your life with someone who challenges you or Bspend your life with someone who comforts you?
29. Would you rather Ahave every question you ask answered or Bnever stop wondering?
30. Would you rather Abe brave once when it really matters or Bbe a little brave every day?
31. Would you rather Ahear what your friends would say about you in a speech or Bread what a stranger would write about your life?
32. Would you rather Abe the reason someone believes in themselves or Bbe the reason someone believes in people again?
33. Would you rather Aknow your true potential or Bnever feel limited by it?
34. Would you rather Astart over in a new city where no one knows you or Bstay where everyone knows you?
35. Would you rather Achange your mind easily or Bstand firm no matter what?
36. Would you rather Abe someone's first love or Bbe someone's last love?
37. Would you rather Ahave deep talks every night or Bhave easy laughs every night?
38. Would you rather Aknow who you'd be if you grew up somewhere else or Bnever wonder about it?
39. Would you rather Agive advice that changes someone's life or Breceive advice that changes yours?
40. Would you rather Abe at peace with your past or Bbe excited about your future?
41. Would you rather Alive in a world where everyone is honest or Blive in a world where everyone is kind?
42. Would you rather Aspend one more day with someone you've lost or Bspend one more day as a kid?
43. Would you rather Abe known by everyone or Btruly know a few people?
44. Would you rather Afollow your heart or Bfollow your head?
45. Would you rather Acarry one memory with you forever or Bcarry one skill with you forever?
46. Would you rather Amake peace with an old friend or Bmake a new friend for life?
47. Would you rather Afeel lonely in a crowd or Bfeel content on your own?
48. Would you rather Ahave a life of quiet meaning or Bhave a life of loud success?
49. Would you rather Abe needed or Bbe wanted?
50. Would you rather Asee yourself the way others see you or Bhave others see you the way you see yourself?
51. Would you rather Aunderstand everyone or Bbe understood by everyone?
52. Would you rather Ahave more courage or Bhave more patience?
53. Would you rather Abe the storyteller or Bbe the story?
54. Would you rather Anever feel regret or Bnever feel nostalgia?
55. Would you rather Aknow what your dreams mean or Bremember every dream you have?
56. Would you rather Aleave the world a little kinder or Bleave the world a little more beautiful?
57. Would you rather Afall in love slowly or Bfall in love all at once?
58. Would you rather Agrow old with your best friend or Bgrow old surrounded by family?
59. Would you rather Aalways know the right thing to say or Balways know when to say nothing?
60. Would you rather Abe proud of your past or Bbe hopeful about your future?

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