300

300 Character
Character
Warm
Warm Up
Up Questions
Questions

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1. Are you a dog person or a cat person and why? 40. Do you have any unusual or nervous mannerisms,
2. Are you a good dancer? such as when talking, thinking, being afraid, under
stress, or when embarrassed?
3. Are you a morning person or a night owl?
41. Do you have any unusual talents?
4. Are you a picky eater or do you like to try new foods?
42. Do you have any vices?
5. Are you allergic to any foods?
43. Do you have high or low standards for others? What
6. Are you greedy or generous? about yourself?
7. Are you reactive or proactive? 44. Do you keep a journal?
8. Are you right handed or left handed? 45. Do you keep any houseplants?
9. Are you usually early or late? 46. Do you know how to swim?
10. Can you be counted on to be on time? 47. Do you like to try new and strange foods?
11. Considering you can't come back, would you rather go 48. Do you like to try new experiences?
to the past or the future?
49. Do you prefer a big city or a rural village?
12. Describe a time that someone did something altruistic
for you. 50. Do you prefer camping outside of town, or staying at
the inn?
13. Describe your perfect afternoon.
51. Do you prefer hunting or fishing?
14. Did you have a childhood pet?
52. Do you prefer to swim in a lake or the ocean?
15. Do you believe in ghosts?
53. Do you prefer to work alone or as part of a team?
16. Do you believe in soulmates? What about love at first
sight? 54. Do you talk in your sleep?
17. Do you consider yourself artistic? 55. Do you think you are more or less attractive than
average?
18. Do you consider yourself well organized?
56. Do you think your friends agree with each other on
19. Do you cook meals or eat out? the kind of person you are?
20. Do you enjoy public speaking? 57. Do you want to be famous or well-known?
21. Do you enjoy surprises? 58. Do you want to settle down with a spouse and kids?
22. Do you enjoy the spotlight or being the center of 59. Do your friends tend to be older or younger than you?
attention?
60. Have you ever been fired or quit a job?
23. Do you feel like you have enough time?
61. Have you ever been in love?
24. Do you feel responsible for anyone besides yourself?
62. Have you ever broken the law and didn't get caught, if
25. Do you follow any gods or deities? so how?
26. Do you have a favorite set of pajamas? 63. Have you ever cheated on a spouse or lover?
27. Do you have a good luck charm? 64. Have you ever cheated on a test? Did you get caught?
28. Do you have a guilty pleasure? 65. Have you ever disliked someone for being luckier or
29. Do you have a notorious or celebrated ancestor? more successful than you?
30. Do you have an insignificant memory that has stayed 66. Have you ever done charity work?
with you all these years? 67. Have you ever gone to a psychic?
31. Do you have any allergies or sensitivities? 68. Have you ever had to get revenge on someone?
32. Do you have any allergies? How severe? 69. Have you ever helped an injured animal?
33. Do you have any catchphrases? 70. Have you ever let someone down?
34. Do you have any colors you dislike? 71. Have you ever stood up to a bully?
35. Do you have any long term goals? 72. Have you ever tended a garden?
36. Do you have any nicknames or street names? 73. Have you kept any toys from childhood?
37. Do you have any noticeable scars? If so, what are their 74. How attractive do you think you are? How attractive
stories? do others think you are?
38. Do you have any phobias? 75. How can someone earn your trust?
39. Do you have any scars, tattoos, or birthmarks? 76. How close are you to your family?

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107. Is there anything that can get a smile out of you no 77. How did you decorate your childhood bedroom?
matter how sad or upset you are? 78. How do you feel about emerging technology?
108. Is your happiest memory behind you or in front 79. How do you like to celebrate your birthday?
of you?
80. How do you like to spend your free time?
109. Name one cool feature you would add to your
dream house. 81. How forgiving are you when your friends let you
down?
110. Omnivore, vegetarian, vegan?
82. How happy are you on a scale of 1 to 10?
111. Teleportation or flying?
83. How much do you feel in control of your life?
112. What advice would you give to your younger self?
84. How would you like to be remembered after you die?
113. What annoys you the most?
85. How would your parents describe you?
114. What are you most embarrassed about?
86. If you could be any age forever what would it be?
115. What are your parents’ names?
87. If you could be any animal in the world, what animal
116. What did you dream about last night? would you choose to be?
117. What do you consider to be the most beautiful 88. If you could choose it, how long do you want to live?
thing you've ever seen?
89. If you could go back and change one decision you
118. What do you consider to be the ugliest thing made in the past, what would you change?
you've ever seen?
90. If you could go on vacation anywhere in the world,
119. What do you daydream about? where would it be?
120. What do you do better than anyone else? 91. If you could only eat one dessert for the rest of your
121. What do you do if you can't sleep? life, what would it be?
122. What do you do to relax? 92. If you could only eat one food for the rest of your life,
123. What do you do when you get bored? what would it be?
124. What do you do with your gear when sleeping? 93. If you could open a restaurant, what would it be like?
125. What do you hope for in the afterlife? 94. If you could retire with a big pile of gold, what would
they do?
126. What do you like most about adventuring?
95. If you could travel anywhere in the world, where
127. What do you look like when you get angry? would you go?
128. What do you smell like? 96. If you could use a voodoo doll to hurt anyone you
129. What do you think is the true meaning of life? choose, would you?
130. What do you want to do after you are done 97. If you had to eat one meal everyday for the rest of your
adventuring? life what would it be?
131. What does it take for you to trust someone? 98. If you had to teach a class on one thing, what would
132. What does your happy place look like? you teach?
133. What does your morning routine look like? 99. If you were guaranteed an honest response, what
question would you ask and to whom?
134. What event can you not forget?
100. If you were involved with a circus, what would you
135. What friend do you miss? be doing?
136. What habits would you find most annoying in 101. If you weren't adventuring what would you be
your party members? doing?
137. What has been your biggest disappointment in 102. In what way will reaching your goals improve
life so far? your life?
138. What have you done to make the world a better 103. Is anything so important you would sacrifice your
place? life for it?
139. What is more important to you: professional 104. Is it easy for you to accept help when you need it?
success or personal happiness?
105. Is there anyone you would trade lives with? If so,
140. What is one food that you simply will not eat? who?
141. What is one way that someone can earn your 106. Is there anything about your past that you would
trust? change?
142. What is something you do every morning?
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180. What job do you think you’d be really good at? 143. What is something you regret not telling
181. What job would you be terrible at? someone?
182. What kind of people do you like to spend time 144. What is the best compliment that you've ever
with? received?
183. What lengths would you go to defend your faith? 145. What is the biggest lie you have ever told?
184. What makes you wistful or nostalgic? 146. What is the biggest mistake you have ever made?
185. What memory do you want to forget the most? 147. What is the furthest away from home you've ever
been?
186. What memory from adolescence has had the most
impact on you as an adult? 148. What is the last present you gave somebody?
187. What one item do you save from a house fire? 149. What is the last thing you do before going to bed?
188. What one thing do you really want but can’t 150. What is the one task you would absolutely refuse
afford? to do?
189. What place do you never want to go back to? 151. What is the tallest tree you have ever climbed?
190. What place have you only heard of and would like 152. What is the worst thing you have done to someone
to visit? you loved?
191. What school of magic best describes you? 153. What is worse, deciding if to kill, or how to kill?
192. What school subject is your favorite? 154. What is your character’s retirement plan?
193. What school subject is your least favorite? 155. What is your favorite art form?
194. What skill do you wish you could wake up with 156. What is your favorite breakfast food?
tomorrow? 157. What is your favorite candy?
195. What sport would you compete in if you were in 158. What is your favorite color?
the Olympics? 159. What is your favorite dad joke?
196. What temperature are you most comfortable at? 160. What is your favorite dessert?
197. What to do with your body when you die? 161. What is your favorite holiday or celebration?
198. What was the best dream you ever had? 162. What is your favorite meal to cook and why?
199. What was the best party you ever went to? 163. What is your favorite memory with your best
200. What was the last meal you had at home? friend?
201. What was the last thing you argued about? 164. What is your favorite physical activity?
202. What was the worst haircut you ever had? 165. What is your favorite piece of furniture?
203. What was the worst job you ever had? 166. What is your favorite season?
204. What was the worst nightmare you ever had? 167. What is your favorite time of the day and why?
205. What was your childhood nickname? 168. What is your favorite weather?
206. What was your dream job when you were 169. What is your idea of a good evening's
younger? entertainment?
207. What was your favorite family tradition as a 170. What is your least favorite food?
child? 171. What is your least favorite weather?
208. What was your first job? 172. What is your life's greatest accomplishment so
209. What was your greatest talent when you were far?
younger? 173. What is your most annoying habit?
210. What was your last nightmare? 174. What is your most favorite pair of shoes you've
211. What was your last pleasant dream? ever had?
212. What would the title of your autobiography be? 175. What is your most treasured memory?
213. What would you do if you had insomnia and had 176. What is your perfect evening?
to find something to do to amuse yourself? 177. What is your spirit animal?
214. What would your major be at university? 178. What is your theme song?
215. What's in your pockets right now? 179. What is your worst nightmare?

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250. What’s your favorite way to relax? 216. What’s on your grocery list?
251. What’s your least favorite chore? 217. What’s one place you've visited that you never
252. When did you last break a promise? want to return to?
253. When did you last sing to yourself? 218. What's one rule you will never break?
254. When was the last time you cried in front of 219. What's one thing that will always make you smile?
another person? 220. What’s one thing you would change about the
255. When was the last time you sang to someone? person you love most in the world?
256. When was the last time you went on vacation? 221. What’s one thing you're determined to do before
you die?
257. When was the last time you were in a place of
worship? 222. What’s something that grosses you out?
258. When was the last time you yelled at someone? 223. What’s something that reminds you of home?
259. When you make a big decision, is it based on 224. What’s something you like to do the old-
feelings or facts? fashioned way?
260. When you tell a story, do you exaggerate or tell 225. What’s something you quit, that you now regret
the truth? giving up on?
261. Where do you feel most safe? 226. What's the best compliment you ever received?
262. Where do you like to hangout? 227. What's the best dream you ever had? The worst
nightmare?
263. Where would you like to retire to?
228. What’s the best haircut you ever received?
264. Who do you admire the most and how do they
inspire you? 229. What's the best lie you've ever told?
265. Who do you look up to? 230. What’s the best meal you've ever had?
266. Who do you pray to? 231. What's the best outfit you ever wore?
267. Who do you trust the least? 232. What’s the best piece of advice you’ve ever been
given?
268. Who do you trust the most?
233. What's the best play you've ever seen? Worst?
269. Who do you wish was here with you now? How
would they make things better? 234. What's the best vacation you ever went on?
270. Who have you been friends with the longest? 235. What’s the best way to start the day?
271. Who is the most important person in your life 236. What’s the first thing you buy for a new home?
and why? 237. What's the funniest thing you overheard at a
272. Who is your biggest rival? tavern?
273. Who is your worst enemy? 238. What’s the furthest away from home you’ve ever
been?
274. Who of anyone in the world do you want to have
dinner with? 239. What's the last joke that made you laugh?
275. Who started the first fight you ever got into? 240. What's the luckiest thing that ever happened to
you?
276. Who trained you in your skilled areas?
241. What’s the most beautiful place you’ve ever been?
277. Who was the last person to insult you?
242. What’s the weirdest thing you have done while
278. Who was your best friend while growing up? drunk?
279. Who would you trust the most with a secret? 243. What's the worst death you've ever seen?
280. Who, if anyone, has significantly influenced your 244. What’s the worst food you've ever had?
life?
245. What's the worst party you've ever been to?
281. Would you change anything about your
appearance? 246. What’s the worst play/street performance you
ever saw?
282. Would you ever lie to the authorities for a friend?
247. What's the worst stroke of fortune you ever had?
283. Would you rather be blind or deaf?
248. What’s your best scar story?
284. Would you rather be hot or cold?
249. What’s your favorite place of all the places you’ve
285. Would you rather be overdressed or underdressed travelled?
for a party?
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286. Would you rather be pretty and die young or be
ugly and live unnaturally long?
Credits
287. Would you rather be successful or happy? by c. mcclain, 2025, Ver 1.0 June 18 2025
288. Would you rather die a hero's death, or peacefully
in your sleep? Some artwork © 2015 Dean Spencer, used with
289. Would you rather have a housekeeper or a permission. All rights reserved. [Link]
personal chef? [Link]/
290. Would you rather have a short intense romance or
a long burning relationship? Support the Creator
291. Would you rather have new experiences with new
people or more time with people you already know? Links - [Link]
292. Would you rather leave home permanently, or inspiration/
never be able to leave?
293. Would you rather live in the ocean or on the Discord - [Link]
moon?
294. Would you rather play a game with someone Ko-fi: [Link]
more or less skilled than you?
Patreon: [Link]
295. Would you rather save a lot of people you don't
know, or a few people you know personally?
Find this table as a random generator at:
296. Would you rather visit a volcano or a rainforest? [Link]
297. Would you take 1 million gold to leave your home
and never return? If not, how much?
298. Would your friends describe you as organized?
299. You can have an unlimited supply of one thing for
the rest of your life, what is it?
300. You’re going sail around the world, what’s the
name of your boat?