One hundred roleplaying questions that you can use to further develop your characters.
| d100 | Entry |
|---|---|
| 1 | If your character wasn’t an adventurer, what livelihood would they lead? |
| 2 | Who in the party would your character trust the most with their life? |
| 3 | What are your character’s core moral beliefs? |
| 4 | What relationship does your character have with their parents and siblings? |
| 5 | Does your character have any biases for or against certain races? |
| 6 | What is your character’s opinion on nobility? On authority? |
| 7 | Describe your character’s current appearance: clothes, armor, scars they’ve picked up along the journey, etc. |
| 8 | What location encountered in the campaign has your character felt the most “at home” in, or just generally liked the most? |
| 9 | What deity, if any, does your character worship? What’s their opinion on other people’s worship? |
| 10 | If your character had time to pick up any artisan’s tools, game set, instrument, etc., what would it be? |
| 11 | Describe your character’s current relationship with the player character sitting to your right. |
| 12 | What is your character’s current goal, summed up in one sentence? |
| 13 | Does your character ever want to “settle down” with a spouse, children, house, etc.? |
| 14 | Has your character ever been in love? |
| 15 | What battle in the campaign has been most memorable to your character? |
| 16 | If your character wasn’t whatever class they are, what would they be instead? |
| 17 | What is your character’s favorite season? |
| 18 | What would your character’s Zodiac sign be, following stereotypical astrology? |
| 19 | Where in the world does your character most want to visit? |
| 20 | What is the biggest mistake your character has ever made? |
| 21 | Does your character have any noticeable scars? If so, what are their stories? |
| 22 | What animal best represents your character? |
| 23 | If your character could go back in time and change one thing about their life, what would it be? |
| 24 | Which other player character does your character find themselves having the most in common with? |
| 25 | Does your character regret any particular choice the party has made? |
| 26 | What would your character say their best trait would be? |
| 27 | What is your character’s greatest fear? Deep, irrational? |
| 28 | What is currently motivating your character to stay with the party? |
| 29 | What are your character’s hobbies and interests outside of their class? |
| 30 | What would most people think when they first see your character? |
| 31 | What stereotypical group role does your character play in the party? (The Mom, the Mess, the Comic Relief, etc. Optionally: What role would your character play in the “Five Man Band” structure?) |
| 32 | What is your character the most insecure about? |
| 33 | What person does your character admire most? |
| 34 | What does your character admire and dislike the most about the player character sitting to your left? |
| 35 | Why is your character’s lowest stat their lowest (the in-character reason, not “because there’s no reason for a wizard to have 16 strength, duh”)? |
| 36 | What would be your character’s theme song/favorite band/favorite genre of music? |
| 37 | What stereotypical role would your character play in a high school AU/if they attended a normal high school? (Nerd, jock, bully, goth, etc.) |
| 38 | What treasure/item/artifact that your character has collected during the adventure is the most important to them? |
| 39 | Is there any particular weapon, item, etc. that your character longs to find? |
| 40 | Where does your character feel the most at home? |
| 41 | Does your character care about how they’re perceived by others? How do they change themselves to fit in with other people? |
| 42 | What does your character think is the true meaning of life? |
| 43 | What is your character’s scent? (Bonus points for a description that sounds like it could be from a bad [or awesome] fanfic.) |
| 44 | Does your character think more with their heart or their brain? |
| 45 | What is your character’s most recent or frequent nightmare? |
| 46 | What opinion does your character have on [CERTAIN ESTABLISHED GROUPS/AUTHORITIES IN THE GAME WORLD]? (Dragonmarked Houses, royal crown, etc.) |
| 47 | How did your character spend their childhood? Where did they grow up/who were their childhood friends? |
| 48 | What aspect of your character’s future are they most curious about? (If they could know one thing about the future, what would it be?) |
| 49 | What colors are associated with your character? |
| 50 | Who in the party would your character prioritize rescuing, in dire circumstances? |
| 51 | Is your character the most swayed by ethos, pathos, or logos? |
| 52 | If your character was granted a single use of Wish, what would they use it for? |
| 53 | What is your character’s favorite spell? If they don’t use spells: what is their favorite personal weapon/combat maneuver/skill/etc.? |
| 54 | How does your character feel about keeping secrets from the rest of the party? |
| 55 | What type of creature in the world is your character the most intrigued by? |
| 56 | When they were a child, what did your character want to be, or think they were going to be, when they grew up? |
| 57 | The player character to your left admits that they’re passionately in love with your character. How would your character respond? |
| 58 | If somebody (an NPC, someone from their backstory, etc.) your character trusts/loves asked your character to do something against the party’s best interest, who would they side with? |
| 59 | Does your character value their own best interest more than the party’s? |
| 60 | What decision would the party have to make in order for your character to consider splitting off from the group? |
| 61 | How does your character imagine the way they will die? |
| 62 | What is your character’s greatest achievement? |
| 63 | Is your character willing to risk the well-being of others in order to achieve their goal? |
| 64 | What is your character’s opinion on killing others? |
| 65 | What is your character’s favorite food? Beverage? |
| 66 | How generous is your character? Especially to those they don’t know? |
| 67 | What is your character the most envious about, regarding anyone in the party? |
| 68 | The player character to your left and the player character to your right are both telling your character two different versions of the truth. Who does your character believe? |
| 69 | What is your character’s sexuality/relationship with sex? |
| 70 | What is your character’s biggest pet peeve? |
| 71 | Describe how your character feels about the party’s current situation/objective/etc. |
| 72 | Who in the party would your character trust the most to keep an important secret? |
| 73 | If your character knew that they were going to die in a month, how would they spend the rest of their life? |
| 74 | What makes your character feel safe? |
| 75 | If your character had the chance to rename the party/give the party a name, no questions asked, what would it be? |
| 76 | What memory does your character want to forget the most? |
| 77 | If your character had to multiclass into a class they currently aren’t the next time they level up, what would it be and what reason would they have for doing so? |
| 78 | What television/book/video game/etc. character would your character be best friends with? (Or: what media character is your character the most influenced by/similar to? |
| 79 | What unusual talents does your character possess? |
| 80 | How does your character feel about receiving/giving orders? Are they more of a leader, or a follower? |
| 81 | What does your character’s name represent to them? (Or: why as a player did you choose your character’s name?) |
| 82 | Is your character more of an introvert, or an extrovert? |
| 83 | How far is your character willing to go to pursue the “greater good”? Do they believe in a greater good at all? |
| 84 | What does your character want to be remembered by? |
| 85 | What would be your character’s major in college? |
| 86 | Does your character consider themselves a hero, villain, or something else? |
| 87 | What major arcana tarot card best represents your character? |
| 88 | Where does your character see themselves in 20 years? |
| 89 | What is your character’s relationship with magic? Are they scared of it, wish to know more about it, indifferent to it? |
| 90 | Who is your character’s biggest rival? |
| 91 | What is your character’s guiltiest pleasure? |
| 92 | What does your character hope for the afterlife? |
| 93 | Who in the party does your character trust the least? |
| 94 | What is your character’s biggest flaw? |
| 95 | How did your character learn the languages that they speak? |
| 96 | What is your character’s favorite school of magic/type of weaponry? |
| 97 | What is most important to your character: health, wealth, or happiness? |
| 98 | What advice would your character give to a younger version of themselves? |
| 99 | Are there any social or political issues your character feels strongly about? |
| 100 | What, currently, is your character the most curious about? |