100 Prompts for Idle Chit-Chat Between Characters

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

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