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