100 deep questions to ask on long autumn road trips


photo via Travel + Leisure

Whether you’re going on college visits, traveling for sports or driving to Szalay’s, chances are you’ve got a lot of road trips coming up. More often than not, you won’t be traveling alone. Knowing how harrowing the formidable awkward silence can be for the most anxious among us, I’ve compiled to follow questions to act as conversation-starters. More than just cannon fodder, however, these questions are meant to help you understand your driving buddy on a deeper level, hopefully strengthening your relationship. And hey: if they help the time pass as well, that’s two birds with one stone.


  1. Do you believe in fate?
  2. What’s the first trait you notice about someone when you meet them?
  3. Where do you see yourself in 10 years? 
  4. What drives you to succeed?
  5. Do you believe people with different fundamental beliefs can be friends?
  6. When did you last cry and why?
  7. Why do you listen to the music that you do?
  8. Which family member has had the most profound influence on you?
  9. Do you believe humans are intrinsically good or evil?
  10. Is there anyone or anything you’d die for?
  11. Is there anyone or anything you’d kill for?
  12. When you think of regrets you have, who is the first person that pops into your mind?
  13. Do you like who you are right now?
  14. Do you believe in second chances?
  15. What do you consider the greatest injustice in the world today?
  16. Who do you feel oppressed by?
  17. In your mind, what makes you stand out?
  18. What is your most toxic personality trait?
  19. Would you rather be called vain or insecure?
  20. Have you ever had your heart broken?
  21. Would you rather have your heart broken or be the heartbreaker?
  22. What do you think inspires marginalization?
  23. Can violence genuinely solve disputes?
  24. What is your greatest insecurity?
  25. If you ruled the world, what’s the first change you’d make?
  26. Have you ever chosen to cut someone out of your life?
  27. Are the friendships you have now stronger or weaker than those you had five years ago?
  28. Would you consider yourself depressed?
  29. Are you a leader or a follower?
  30. Has the world changed for the worse or for the better in the last 10 years?
  31. What is your weirdest irrational fear?
  32. How do you want to be perceived by your peers?
  33. How do you define evil?
  34. How do you define good?
  35. Are there fundamental beliefs you hold that you choose not to share with anyone?
  36. If told you had only a week to live, what would you do?
  37. Have you ever made someone cry?
  38. Do you believe lying is ever justified?
  39. What are you most dreading right now?
  40. What would you change about the school system if you could?
  41. What do you consider your top three priorities?
  42. Have your priorities changed in the past year?
  43. What do you wish you could tell your parents?
  44. What skill does everyone but you seem to have?
  45. Do people really change, or do they just show their true colors?
  46. Are you afraid to die?
  47. If you had the chance to find out how you’ll die, would you take it?
  48. Do you change your personality based on who you’re interacting with?
  49. Has a heated argument with someone ever genuinely changed your mind?
  50. What is the value of art in society?
  51. Is world peace possible?
  52. Do the people you romantically pursue align with what you say your “type” is?
  53. Would you stay with someone who cheated on you?
  54. Is there anything in life that isn’t worth learning?
  55. What is your worst memory from grade school?
  56. Do you think you’ll make a good parent (and do you want to be one)?
  57. Do you like company when you’re sad?
  58. Would you be friends with you?
  59. Do you believe in heaven and hell?
  60. What would you consider yourself addicted to?
  61. Is there any behavior you preach but don’t practice?
  62. Who would be most affected if you were never born?
  63. What would you want to be famous for?
  64. What qualities make someone a good teacher?
  65. Do you think you give good advice?
  66. If you were rich enough to end world hunger, should you be forced to do so?
  67. Have you ever hit rock bottom?
  68. Do you believe that everyone you meet teaches you something?
  69. Do you have a healthy relationship with religion?
  70. Are there any conspiracy theories you genuinely believe?
  71. Is there anyone you feel justified in mistreating?
  72. Have you learned anything life-changing from reading a novel or poem?
  73. Do you consider yourself too young to fall in love?
  74. What do you want your last words to be?
  75. Why aren’t you chasing your passion?
  76. What’s the worst feeling in the world?
  77. Would you change the past if you could?
  78. Do you keep your friends close and enemies closer?
  79. What’s something you only do when you’re home alone?
  80. Is there someone from your past you wish you could reconcile with?
  81. If you could share a meal with three people, who would you choose?
  82. If you died right now, do you think you’d go to heaven?
  83. Is there any action beyond repentance?
  84. What’s something you’ve never said out loud before?
  85. How long does it take you to fall in love?
  86. What’s the nicest compliment you’ve ever received?
  87. What do you wish someone would compliment about you?
  88. What is the worst thing someone has ever said to you?
  89. Is there a good way to reject someone?
  90. Do you have a good relationship with your body?
  91. Would you ruin someone else’s life if it meant you’d be happy forever?
  92. Do you ever feel like you’ve wasted your life up to this point?
  93. Are there people you think you know better than yourself?
  94. How do you cope?
  95. When was the last time you were rejected?
  96. What song or movie sparks a poignant memory in your mind?
  97. Do you feel appreciated by your friends?
  98. What are you doing on Purge Day?
  99.  Why are we afraid to show people we care?
  100. Has your answer to any of these questions been a lie?