Turning small talk into real talk.
Part 3 of “Questions” starts with digging deeper into someone’s values.
“In learning about someone’s values, you are learning about their owner’s manual,” Hendrix explains. Even seemingly mundane questions can get at a person’s values—like what’s motivating them to do well on a presentation or what they look for in an S.O.
“By learning about someone’s life philosophy, you’re able to get at their true essence, how they live their life, and what drives their actions,” Orbuch adds.
That said, you can’t just ask, “What are your values.” What you can ask:
121. What’s a relationship deal breaker for you?
122. If you had only one sense (hearing, touch, sight, etc.), which would you want?
123. What is your definition of success?
124. Are you at all religious or spiritual?
125. What are you most proud of in the last year?
126. What makes you feel most accomplished?
127. Who do you admire most in the world?
128. If you won a million dollars, what would you do with the money?
129. Which of your personality traits are you most proud of?
130. What’s the first thing you look for in a partner and/or friend?
131. How did you form your current political views?
132. Do you live by any piece of advice or motto?
133. How can someone earn your trust?
134. How can someone lose your trust?
135. Would you rather someone be honest and hurt your feelings or lie to protect them?
136. If you could snap your fingers and instantly make the world better, what would you do?
137. Do you believe in astrology? Why or why not?
138. Have you ever lost a friend? If so, what happened?
139. If you could only teach one thing to your (future) child, what would it be?
140. What’s the scariest thing you’ve ever done, and why did you do it?
141. Do you believe in second chances?
142. Where do you get your news?
143. What is your biggest irrational fear?
144. Do you contribute to any charities?
145. When was the last time you volunteered?
144. Are you an organ donor?
145. Do you believe you should do one thing a day that scares you?
146. What, if anything, do you think happens after death?
147. What line should someone never cross with you?
148. How do you define beauty?
149. Do you believe in life on other planets?
150. How do you interact with someone who disagrees with you?
“These questions get at what the person is motivated by,” says Orbuch. “What gives them the strength to wake up every day and get going? What do they dream and think about in their day?” When you learn about someone’s dreams, you share something more intimate. Jumpstart a deep conversation by asking this:
151. If you could do anything, besides what you’re doing now, what would you do?
152. What do you regret not doing in the last year?
153. What’s on your bucket list?
154. If you had unlimited money to start your own business, what would it be?
155. If you found out today was your last day on Earth, what would you do?
156. If you could live anywhere in the world, where would it be?
157. A genie gives you three wishes—what are they?
158. If you had the opportunity to be immortal, would you take it?
157. If you could time travel, when and where would you go?
158. Do you think you’ll likely accomplish all your dreams?
159. If you could magically become famous, would you want to?
160. If you could relive one moment in your life, which would it be?
Last, we have:
Sometimes the oddball questions allow you to learn the most interesting things about a person. “Unusual questions allow you to see the varied, unique, and special qualities of a person—their answers give you personal information about what makes them tick,” Orbuch says. “These questions also typically get the other person to think outside box and really ponder something.” Ask these ~unconventional~ questions, and you’ll definitely get some surprising answers:
161. If you see a puddle on the ground, do you walk around it or over it?
162. If you could have a super power, what would it be?
163. If you could go back to anytime in history, where would you go?
164. If you came back in your next life as an animal, what animal would you be?
165. If you got to name a new country, how would you decide what to call it?
166. What would be the title of your memoir?
167. Do you hit the snooze button or wake up immediately?
168. What’s the first thing you do in the morning?
169. What’s the last thing you do at night?
170. Do you believe in any conspiracy theories (no judgement)?
171. Do you think iced coffee should only be consumed in the summer or all year round?
172. Would you rather be covered in fur or covered in scales?
173. What’s your idea of a perfect date (yes, of the calendar year)?
174. What’s the most unusual place you’ve fallen asleep?
175. At a party, where can someone find you?
176. Do you wash your legs in the shower?
177. Who would play you in the movie of your life?
178. When making a PB&J sandwich, do you put on the peanut butter or jelly first?
179. Do you have any allergies?
180. Do you trust your own memory? Why or why not?
181. Which fictional character do you relate to most?
182. What, if anything, would make you walk out in the middle of a movie?
183. When was the last time you cried and why?
184. What’s your most controversial opinion?
185. Do you “stan” any celebrities?
186. What’s your go-to drunk snack?
187. What was your all-time favorite Halloween costume?
188. What’s the weirdest thing you do when you’re alone?
189. Do you have any recurring dreams?
190. What’s the silliest argument you’ve ever been in?
191. What’s the worst argument you’ve ever been in?
192. What’s your opinion on modern art?
193. If you could choose how to die, would you? If so, what would you choose?
194. What’s the most ridiculous outfit you’ve ever worn?
195. What was the first thing you wanted to be when you grew up?
196. If you could own a mythical creature (unicorn, phoenix, etc.), which one would you pick?
197. What’s your least favorite place in the world?
198. Would you rather have your dishes or clothes be magically clean?
199. What’s your favorite story about yourself?
200. If you could change anything about yourself, would you? If so, what and why?
“Anytime you reveal personal information to someone else, it increases intimacy between you and the other person,” says Orbuch. So let down your guard, and don’t be afraid to ask (or answer!) these deep questions.
So, there you have it, 200 questions to ask someone to get to know him/her better.