1. What’s one thing that’s happened to you that has made you a stronger person?
2. What’s one thing that’s happened to you in your life that made you feel weak?
3. Where is one place you feel most like yourself?
4. Where is your favorite place to escape to?
5. Who do you think has had the largest influence on the person you are today?
6. If you could change one thing about yourself what would it be?
7. If you had one day left to live, what would you do first?
8. What decade do you feel you most belong in?
9. Who are you closest to in your family? Why?
10. Who is the one person in this world that knows you best?
11. What is your favorite quality about your best friend?
12. When you were younger what did you think you were going to be when you grew up?
13. If you could identify with one fictional character (from a book, show, or movie) who would it be?
14. Do you easily accept compliments? Or do you hate compliments?
15. Is your favorite attribute about yourself physical or non-physical?
16. What is your favorite physical attribute about yourself?
17. What is your favorite non-physical attribute about yourself?
18. Do you believe in love at first sight?
19. Do you believe in soul mates?
20. How seriously do you take horoscopes?
21. Have you ever been in love? How many times?
22. What makes you fall in love with someone?
23. What does vulnerability mean to you? What has the ability to make you vulnerable?
24. What’s one thing you’re scared to ask a man, but really want to?
25. If you were a man for a day, what would be the first thing you do?
26. What do you find most attractive about each sex?
27. What’s one thing you’d love to learn more about?
28. What is something you’ve never done that you’ve always wanted to do?
29. Why haven’t you done it yet?
30. If money didn’t matter, what would your dream job be?
31. If you had off from work today, what would you do?
32. What was the last thing that made you cry?
33. What was the last thing that made you laugh?
34. What is your favorite memory?
35. What’s the last thing that REALLY embarrassed you?
36. What is your biggest fear?
37. Do you have any regrets? What’s your biggest one?
38. Have you ever broken a law? If you haven’t what is one law you’d love to break?
39. What is the craziest thing you’ve ever done?
40. Would you have a conversation with a stranger?
41. Would you tell a stranger they have toilet paper hanging from their shoe? Or their dress tucked into their underwear? (Or anything else that is embarrassing to be seen in public)?
42. What’s your favorite joke?
43. Are you a dog person or a cat person?
44. If you could be any animal, what animal would you be?
45. What’s one show, movie, or book, you’re embarrassed to admit you enjoy?
46. How do you think your parents would describe you as a child?
47. If you could go back to any age or time of your life, what age or time would it be?
48. What’s something you believe in that not everyone else does?
49. What’s one thing you would say that makes you unique from other people?
50. What is one thing you feel your life is missing?
51. What’s your favorite inspirational quote?
52. Which college course (or high school class) did you find the most engaging?
53. How many books do you read per month?
54. Who is the smartest person you’ve ever met?
55. What’s the most interesting autobiography that you’ve ever read?
56. What childhood event do you think impacted you most as a person?
57. What’s your favorite TED Talk of all time?
58. How many answers do you usually get right during Jeopardy?
59. If you had to give a commencement speech at a college, what would you tell the graduates?
60. Which newspaper (or website) do you get your news from?
61. Which fiction author would you love to sit down and have a chat with?
62. What do you wish you cared less about?
63. Do you believe in fate or free will?
64. Do you prefer crosswords or word searches?
65. What cliche saying do you hate hearing the most?
66. Is there a film that changed your entire outlook on life?
67. Do you consider yourself a good person?
68. Who (or what) gives you the most motivation?
69. Do you believe in karma?
70. Do you take better care of your mind or your body?
71. What profession do you have the most respect for?
72. Did your mother or father teach you more about life?
73. What subject do you know the most about — aside from the one you majored in?
74. Which song lyric speaks to you the most?
75. Do you prefer to type or write with a pen?
76. What’s the worst time period that you could possibly travel back to?
77. What do you daydream about?
78. What television or movie character do you feel a bond with?
79. Have you ever had an out of body experience?
80. Do you lie to yourself?
81. Which invention would be impossible to live without?
82. If past lives existed, what do you think yours was?
83. What was the most interesting documentary you’ve ever seen?
84. What do you think the most impressive thing about the universe is?
85. How important is money to you?
86. Do you think you could survive life in prison?
87. Which one of the five senses do you deem most important?
88. What’s your favorite constellation?
89. What was the most stimulating discussion you’ve ever had?
90. Do you have a hunch about how you’re going to die?
91. Are you proud of yourself?
92. Would you rather explore space or the deep sea?
93. What’s your spirit animal?
94. How often do you pray, if ever?
95. What’s the most fascinating random fact you know?
96. Is there any motivational speech from a celebrity that sticks out in your mind?
97. Do you trust your head or your heart more?
98. What genre of books do you prefer?
99. Do you enjoy films with subtitles?
100. Do you consider yourself to be an intelligent person?
101. What is the real story behind the last Instagram picture you posted?
102. What do you consider the most beautiful word in the English language?
103. Do you screenshot the sweet texts that people send you? What is the last one you’ve received?
104. If you competed on a game show, which charity would you play for?
105. What is the last thing you wrote by hand instead of typed?
106. Which song do you always end up playing during long drives?
107. If you had to guess, what color is your aura?
108. Do you know your love language?
109. Which romantic gesture do you believe is overrated?
110. What small act of kindness do you believe is underrated?
111. Which piece of makeup gives you the most confidence?
112. What is the one compliment that people always seem to give you?
113. When was the last time you gave someone a second chance?
114. What is something you wish more people knew about you?
115. Do you hope to grow up to become more like your mother or your father?
116. What has changed the most about you since graduating high school?
117. Which milestone are you most proud of reaching thus far?
118. When was the last time you complimented a complete stranger?
119. Which pet name do you find the cutest (sweetie, honey, babe, etc.)?
120. Do you have trouble accepting compliments?
121. Who is the strongest woman that you personally know?
122. Where do you escape to when you want peace and quiet?
123. Do you believe in miracles? Have you ever experienced one?
124. If you wrote a book, who would you dedicate it to?
125. Which emojis do you use the most?
126. Do you feel comfortable in silence?
127. Does your family have any nicknames for you?
128. What do you think about more than you should?
129. Do you consider yourself a romantic or a skeptic?
130. What is the kindest thing another person has ever done for you?
131. What is your favorite candle scent to fill your home wih?
132. What is the most surprising item on your bucket list?
133. Do you believe you have a greater purpose?
134. When was the last time you told someone you loved them?
135. Which day from your childhood do you wish you could relive?
136. How many people would you trust with your life?
137. What do you take the most pictures of (food, your pet, yourself, etc.)?
138. What do you consider the most beautiful thing about your personality?
139. What is your spirit animal?
140. Which season do you look forward to all year long?
141. What qualities do all of your closest friends have in common?
142. What song would you love to hear on your wedding day?
143. Which memory do you wish you could erase from your mind?
144. When was the last time you cried inside of a bathroom stall?
145. What have you been putting off for far too long?
146. Which person never fails to put a smile on your face?
147. Which book have you reread again and again?
148. What is the most romantic proposal story you have ever heard?
149. Can you honestly say that you love yourself?
150. Do you have anything you want to ask me?
151. What about me made you fall in love?
152. Can you see yourself spending the rest of your life with just one person?
153. What is one thing you absolutely won’t compromise or sacrifice for a relationship?
154. How do you think you and I are different from one another?
155. Do you see our differences as a positive or a negative?
156. How do you think we’re similar to one another?
157. Do you see our similarities as a positive or a negative?
158. Do you believe that love can make people overcome their differences?
159. Fast forward 30 years, where do you see yourself?
160. If life’s circumstances forced us to be apart for over a year, would you want to stay together?
161. What does commitment mean to you?
162. In your opinion, what is considered cheating?
163. If you were tempted to be unfaithful would you?
164. If I were unfaithful to you, and asked you to forgive me, do you think you could?
165. Is trust something you think can be rebuilt? Or when it’s destroyed, it’s gone for good?
166. How do you comfort the people you care about when they’re upset?
167. What makes our relationship different from other couples?
168. What makes our relationship different from any other relationship you’ve had before?
169. What about me first attracted you?
170. Do you think our connection was instant?
171. How has our connection changed since we first met? Stronger? Weaker?
172. Are there things we do together that you would rather do on your own?
173. What in our lives do you think we should keep separate, or want to keep separate? What types of things do you feel we don’t need to do together?
174. What are the things you think we should always do together?
175. What do you want emotionally from a partner?
176. If you could live anywhere, where would you live?
177. Would you rather live in one place for a very long time or live in many places and move around?
178. What would make you leave someone you love?
179. Is there anything about our relationship that makes you feel lonely or unloved?
180. Would you trust me with something that you wouldn’t trust with anyone else?
181. Are there ways you show love that you think I don’t understand or pick up on?
182. What does intimacy mean to you?
183. If I were to in someway be unfaithful but it meant nothing, would you want me to tell you?
184. If you were to in someway be unfaithful but it meant nothing, would you tell me?
185. What are the things you say that are sometimes different from what you mean? (If you say nothing is wrong, do you usually mean it?)
186. What do you think is the best way to solve conflicts?
187. How do you feel about faith and spirituality?
188. What does family mean to you?
189. Do you like kids?
190. Do you want kids of your own?
191. If you were to have children, how would you raise them?
192. What type of people would you wish your children would be?
193. If you were tempted to cheat on me with someone would you tell me?
194. Would you want me to tell you if I was tempted to cheat with someone?
195. Is there anything about me as a person or my behaviors that you question?
196. What little things do you think I sometimes take for granted in our relationship?
197. What little things do you think you sometimes take for granted in our relationship?
198. Are there certain things we’ve never done together that you really want to do?
199. Would you go somewhere with me you’ve never been?
200. What does forever mean to you?
201. Which astrological sign do you never want to date? Why?
202. Which TV family reminds you the most of your own family?
203. What kind of personalities are you the most uncomfortable around?
204. Are you usually the one who cares more or who cares less?
205. What’s the worst fuckboy experience you have ever personally gone through?
206. What is one thing you hope you accomplish by the end of the year?
207. Who do you think you deserve an apology from?
208. Do you check your Instagram stories to see if someone specific watched them? Who?
209. Since you’ve turned 21, what’s the longest amount of time you have gone without drinking?
210. What music do you listen to when you need background noise?
211. What was the most abnormal thing about your childhood?
212. Has anyone ever given you an actual reason why they broke up with you? What was it?
213. Have you ever dated someone while you were still in love with someone else?
214. Who is your favorite Thought Catalog writer?
215. Are you in any one-sided friendships?
216. Which restaurant do you wish existed in your state?
217. What are the most encouraging words your parents have ever spoken to you?
218. Who is the most famous celebrity you have ever met in person?
219. When you read the newspaper (or a magazine) what is the first section you flip to?
220. How do you think you’ve changed the most since you were in high school?
221. Have you ever bullied someone?
222. Has your favorite color changed since you were a kid?
223. Which canceled television series do you wish they would bring back for one more season?
224. Which 90s show do you wish they would reboot on Netflix?
225. What excuse do you most commonly use to get out of plans?
226. Would it be easier for you to give up your phone or your laptop?
227. In your opinion, what is the worst way for someone to propose?
228. What’s the weirdest app you have on your phone?
229. What is one thing you should know how to do by your age, but still can’t figure out?
230. If you could change your first name, what would you change it to?
231. What classic book do you hate?
232. How many friends from childhood do you still keep in touch with?
233. Do you consider yourself a strong person?
234. Do you like movies that make you cry? Or do you avoid them?
235. How many times have you truly hated someone? Who?
236. What is your favorite word in the English language?
237. Do you prefer saying goodbye or ghosting?
238. What is the most bizarre thing you consider a deal-breaker when dating?
239. As a teenager, did you ever get detention? Why?
240. What are your most commonly used emojis?
241. What are some emojis other people use all the time that you have never used once?
242. What’s the closest you have come to marrying someone?
243. How much thought have you put into your future wedding?
244. What phrase did you once use ironically, but has now become a part of your vocabulary?
245. What color pen do you prefer writing in?
246. Not who, but what, do you miss?
247. What is your favorite roller coaster you have ever ridden?
248. Would you want to date someone exactly like you?
249. Has a pickup line ever worked on you?
250. Do you consider yourself an old soul?
251. If you could go back and relive one year from your childhood, which year would it be and why?
252. If you had to switch your career path right now to something totally different – and money was going to be no issue at all – what would you choose to do for a living?
253. If you could find out exactly what your life was going to be like in ten years from now, would you want to know?
254. If Hogwarts was real and your child received a letter, would you let them go?
255. If you were going to live in a nice, average house but one room in the house could be absolutely incredible, modern, and beautiful – which room would you choose? Bedroom, bathroom, family room, kitchen, etc?
256. If you were given the option to give $10 million to charity or to take $5 million for yourself, which option would you choose?
257. If you could redo just one decision of your life (so far), which decision would you alter?
258. If you could learn the answer to one of history’s unsolved mysteries, which one would it be?
259. If you had to lose one of your five senses, which one would it be?
260. If you could be an Olympic gold medalist, what sport would you want it to be in?
261. If you could be on the writing staff of any tv show in the world, current or from the past, which show would you want to be a writer for?
262. If you had the option of choosing between a chauffeur, a live-in chef, a personal stylist, a masseuse, and a round-the-clock assistant for the rest of your life – at no cost to you – which option would you go with?
263. If you could go back in time and tell off someone who hurt you, who would it be, and what did they do?
264. If you could get a free one-hour life counseling session from any celebrity or famous person in the world, who would you choose?
265. If you had the opportunity to learn exactly what every person in your life really thinks about you, would you take it?
266. Aside from water, if you could only drink one other beverage for the rest of your life (alcoholic or non-alcoholic), what would it be?
267. If you had to give up one of your limbs in exchange for there being a cure for cancer, would you do it?
268. If you said yes to the question above, would you still do it if no one ever found out that you’re the reason cancer was cured?
269. If you could get a $10,000 raise right now but it would decrease all of your coworkers’ salaries by $1,000 each (and they never knew it was your fault), would you do it?
270. If you could choose any super power in the world, what would you choose?
271. If you had to cut off all communication with one of your best friends for five years, who would it be?
272. If you had to cut off all communication with one of your close family members for five years, who would it be?
273. If you had to read one celebrity memoir over and over again for the rest of your life, whose book would you pick?
274. If you could accomplish any heroic feat in the world but no one would ever know it was you (solve world hunger, instigate world peace, etc), what would you choose?
275. If someone paid you a million dollars to wear the same exact outfit every day for the rest of your life, would you do it?
276. If you could be a famous athlete, model, comedian, or serious actor, which option would you choose?
277. If you had to settle down in one place for the rest of your life, where would it be?
278. If there was only one insult word you could use against people for the rest of your life, which word would you pick?
279. If you could talk to any type of animal in the world, what would you choose?
280. If you could immediately have your dream body but it would give your best friend twenty extra pounds, would you do it?
281. How would you spend your free time if you could never watch tv, read a book, or spend any of your time on any smart device ever again?
282. If you had to marry a celebrity who was the opposite of the gender you’re normally attracted to, who would you pick?
283. Taking a shower, brushing your teeth, washing your clothes. You can only pick 2 out of the 3 for the rest of your life. Go.
284. Would you rather have an infinite number of good friends, or two incredible, loyal, absolute best friends?
285. If you could only communicate with one other person for the rest of your life – other than your significant other – who would you choose?
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