100 Prompts for Idle Chit-Chat Between Characters

One hundred roleplaying prompts for your characters while they are traveling.

Full List

  1. You and x recall the first time you met.
  2. You and x got into an argument, what was it about?
  3. There's an old saying among your people...
  4. You and x discuss philosophy. What is the meaning of life?
  5. You picked up a small souvenir in the last town and want to show it off to x. What is it?
  6. There is a competition in (town), you and x make a bet.
  7. If you could have a pet, what would you get?
  8. This area is famous for its (food/drink). What is it?
  9. Do your best x imitation
  10. There is a song stuck in your head. You ask X to help you identify it.
  11. You and x discuss philosophy: Could the Gods create something they could not destroy?
  12. You and x discuss favorite alcoholic drinks
  13. What landmark do you most want to see?
  14. You notice there's something different about x. Guess what change they did.
  15. Would you kiss a goblin?
  16. Someone farted. Determine who did the deed.
  17. There's an auction in a nearby town! Rumor has it they have an item you're interested in. What is it?
  18. You've heard rumors about (town). What was it?
  19. You and x discuss philosophy. Is someone born evil? Can an evil person ever be made good?
  20. What would you do if you were king?
  21. If you owned a Tavern, what would you call it?
  22. This weather reminds you of the time...
  23. You and x discuss philosophy. What is the greatest evil?
  24. You and x recount a prior adventure differently and get into an argument. Each gives their version of events.
  25. You and x reminisce about previous adventures and swap war stories
  26. You and x decided to play a roadtrip game to pass the time. It has now devolved into a heated debate.
  27. Someone ate your lunch. What are you going to do about it?
  28. There's an old story you've heard about the nearby woods. What is it?
  29. You and x discuss your favorite animal...and which would win in a fight.
  30. Describe the last time you got drunk. X describes what really happens.
  31. You decide to teach x how to swear in your language (or a rude gesture in your culture)
  32. You've heard of a strange festival in this area. What is it?
  33. You and x discuss philosophy. What would you use a Wish on?
  34. Who in your group would you want to fight the least?
  35. You had a nightmare and confided in x, what was it?
  36. You and x discuss philosophy. Where do you go when you die?
  37. You and x discuss the value of honor in Adventuring.
  38. What was the worst tavern you ever stayed in?
  39. Isn't this the region (important figure) comes from? Tell us who they are.
  40. You and x reminisce about a former companion. Who were they?
  41. You have an old friend who retired from the Adventuring Life and set up a shop in the region. What was it called again?
  42. You are writing a letter, x is bugging you to reveal the details.
  43. What do you name the Wagon?
  44. You and x play 'Would You Rather?'
  45. Being in such a confined space you begin to notice that x has an odor. Descretely try to inform them without alerting the others
  46. You and x are in a pranking war. What is the next prank you're plotting for them?
  47. You tell the group a true ghost story.
  48. X saved your life once, what were the events surrounding it?
  49. You and x compare romantic tastes and discuss what's best in a potential partner.
  50. What do most people you encounter immediately assume about you?
  51. You and x discuss philosophy. What does a fulfilled life mean to you?
  52. What's the next town famous for?
  53. X had an awkward incident at your last stop and you saw it. What was it?
  54. What creature would you most want to ride?
  55. What do you hope is in the next town?
  56. There is a sign along the road that reads 'GOD IS REAL'. You and x discuss which God you think it's referring to
  57. You and x discuss: if you weren't an Adventurer, what would you like to do instead?
  58. If a Bard were to sing a song, what would you hope they would say?
  59. You and x plan your next night on the town.
  60. You and x discuss philosophy. What is the greatest good?
  61. You and x get into a petty disagreement. The only resolution is a thumbwar.
  62. Everyone plays two truths and a lie.
  63. Your desperate to stretch your legs, what's the first thing you want to do when this wagon stops?
  64. You've heard rumors about the mayor of (town). What was it?
  65. You and x speculate about what might be out in the wilderness beyond the road.
  66. Your seat is uncomfortable, see if you can convince x to switch.
  67. There's a sign for your favorite band along the road. They're on tour! Share your excitement!
  68. Everyone plays a round of Curse/Marry/Shag: pick 3 random Humanoid Monsters
  69. You decide to mess with x with a fake story.
  70. There was a play you recently saw. Recount it. X may disagree.
  71. There was a creep at the last tavern who wouldn't leave you alone. Share the experience
  72. You and x reminisce about previous lovers and swap love stories
  73. You and x play Cows and Graveyards to pass the time. A heated debate over whether a Minotaur counts erupts
  74. X slighted you over dinner. What did they do?
  75. You've been to (town) before, what was it like?
  76. You and x discuss philosophy: Is it better to be a slave living safely, or to be free living under constant risk?
  77. What's your least favorite food/drink?
  78. The barmaid in the last town caught your eye, x teases you about it.
  79. You consider your a lover of nature...except for those damn (animal)
  80. You shared a secret with x, what was it?
  81. You and x make a bet. Whats' the wager over and for how much?
  82. You and x discuss philosophy: What happens after Death?
  83. You and x play The Alphabet Game to pass the time. A heated debate over whether non-Common letters can be counted erupts
  84. You and x discuss philosophy. Does luck exist? Manipulate luck?
  85. There's a recent fashion trend among adventurers. What is it? You and x discuss.
  86. Remind x that they owe you one. What do they owe you and what for?
  87. This road reminds you of the time...
  88. X tells you a story, you call bullshit.
  89. You had a dream and really want to share with x.
  90. You and x discuss philosophy. What is the best way to die?
  91. There's a sign for the next tavern that claims to have the 'Best in the Realm' for your favorite food. Convince the rest of the party to investigate
  92. There's a local legend around these parts. What is it?
  93. Your character cannot pronounce a certain word, x decides to help
  94. You and x discuss the worst parts of Adventuring Life
  95. You and x discuss your biggest fears.
  96. You and x strategize: You give a hypothetical scenario and x thinks of a way out.
  97. X convinced you to try something new, what was it and what did you think of it?
  98. Who in your group do you respect the most?
  99. You and x discuss philosophy: What is the difference between People, Monsters and Animals? Is it strictly their nature or can you turn a Monster into a Person?
  100. There's a temple in this region that is rumored to have an odd ritual. What is it?

Thank you to reddit user u/LilGriff for providing this list!

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