One hundred roleplaying prompts for your characters while they are traveling.
| d100 | Entry |
|---|---|
| 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? |