200 Questions
200 Questions
"Asking someone about their preferences helps you to understand who they
are as a person," says Rebecca Hendrix, LMFT, a therapist in New York. The
important thing here is to go deeper by asking follow-up questions. For
example, "If you find out they like dogs, take it a bit deeper by asking them
what they like most about their dog or their favorite breed," Hendrix explains.
"Commonalities often open the door for further conversation and, once that
door is open, you can start a dialogue that allows the other person to
elaborate and not give close-ended answers," Williams adds.
3. What was the best vacation you ever took and why?
4. Where’s the next place on your travel bucket list and why?
5. What are your hobbies, and how did you get into them?
13. If you could only eat one food for the rest of your life, what would it be?
16. How old were you when you had your first celebrity crush, and who was
it?
17. What's one thing that can instantly make your day better?
20. What song always gets you out on the dance floor?
30. What would be the first thing you'd do if you won the lottery?
35. What’s your favorite content genre (horror, sci-fi, rom-com, etc.)?
37. What’s the worst gift you’ve ever received, and what did you do about it?
Career
No matter how a person feels about their job, the fact is, tons of people
spend a lot of time and energy at work. To help you get to know someone
better, "facilitate a conversation where you are left knowing how they feel
about their career," Hendrix says.
Just prepare yourself to return that openness when they ask the same of you
and your work life. "Initial conversations set the tone for if the person wants
to continue to get to know you, so be ready to answer some questions as
well," Williams says.
47. What’s the first thing you do after getting home from work?
51. Do you have a morning routine at work? If so, what it’s like?
52. Are you able to work from home, and if so, do you enjoy it?
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57. What type of role do you want to take on after this one?
58. Are you more of a "work to live" or a "live to work" type of person?
59. Does your job make you feel happy and fulfilled? Why or why not?
60. How would your 10-year-old self react to what you do now?
64. What originally got you interested in your current field of work?
66. Have you ever had a side hustle or considered having one?
70. What career advice would you give to your younger self?
73. Are you looking forward to retiring, or do you plan to work as long as
possible?
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80. When you started your current job, what most surprised you?
81. How do you pick yourself back up after making a mistake at work?
83. What's one work-related thing you want to accomplish in the next year?
84. Who has had the biggest impact on your career choice?
86. If you could do it all over again, would you pursue the same career? Why
or why not?
87. Does your work routine vary, or does it look the same every day/week?
90. Would you ever relocate for work, if you were asked to?
Family
A great way to get to know someone on a more personal level? Learn about
the people they love. "Asking questions about close relationships can lead to
stories, and sharing stories leads to connection and an experience of being
seen by one another," Hendrix explains. Try:
94. Who do you most like spending time with and why?
96. How has your opinion of your family changed over the years?
97. If you’re close with your family, what’s the hardest part about spending
time away from them?
98. Do you wish you had a bigger family, or are you happy with its current
size?
99. Which family member has had the greatest impact on you?
105. If you could change your relationship with a family member, would
you? If so, with whom?
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109. What’s the best piece of advice a family member has given you?
111. Did you ever hide anything from or lie to your parents?
112. What's your favorite way to spend time with your family?
115. What's the most important holiday you spend with your family and why?
116. What's something your family would be surprised to learn about you?
123. What stories did your family members tell you growing up?
129. What activities did you love to do with your family growing up?
131. If you're adopted, have you met any of your biological relatives?
132. Would you rather go back in time to meet your ancestors, or travel into
the future to meet your descendants?
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:
138. Do you believe time you enjoy wasting is not wasted time?
139. What life lessons have you had to learn the hard way?
140. Do you believe what is meant for you will never miss you?
141. Have you ever experienced true love, and how did you know?
143. If you had only one sense (hearing, touch, sight, etc.), which would you
want?
146. Would you rather make more money doing a job you hate or less doing
one you love?
147. Which of your personality traits are you most proud of?
148. What’s the first thing you look for in a partner and/or friend?
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152. Would you rather someone be honest and hurt your feelings or lie to
protect them?
153. If you could snap your fingers and instantly make the world better, what
would you do?
156. If you could only teach one thing to your (future) child, what would it be?
157. What’s the scariest thing you’ve ever done, and why did you do it?
161. Are you active on social media, or do you prefer to be more private?
162. What is your definition of success?
163. Are you an organ donor, and how did you come to that decision?
164. Do you believe you should do one thing a day that scares you?
169. How do you interact with someone who disagrees with you?
172. What's one thing you can't live without, and why?
Dreams
"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:
177. When you want to give up, what keeps you going?
181. If you could do anything, besides what you're doing now, what would
you do?
185. If you found out today was your last day on Earth, what would you do?
186. If you could live anywhere in the world, where would it be?
187. If you could relive one moment in your life, which would it be?
188. If you had the opportunity to be immortal, would you take it?
189. Which famous person in history would you want to spend the day
with?
190. If you could time travel, when and where would you go?
192. If you could magically become famous, would you want to?
195. Is there anything holding you back from living your ideal life?
196. What steps, if any, are you taking towards your dreams?
198. What's one thing you would do if you knew you couldn't fail?
Unconventional Questions
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."
But you still want to keep things PG, says Williams. "Be careful with asking
questions of a sexual nature too early," she advises. Same goes for the
unconventional-for-a-reason q's, a.k.a. anything related to another person's
finances, but especially questions about child support, debt, and credit score.
Ask these ~unconventional~ questions, and you'll definitely get some
interesting (in a good way!) answers:
200. Do you believe in ghosts—why or why not? (Bonus question: If so, are
you afraid of ghosts?)
204. If you could live in a movie, which one would it be and why?
208. How many hours do you get to the airport before a flight?
215. What’s your idea of a perfect date (yes, of the calendar year)?
222. What, if anything, would make you walk out in the middle of a movie?
223. When was the last time you cried and why?
232. Would you rather have your dishes or clothes be magically clean?
234. If you could change anything about yourself, would you? If so, what and
why?
239. If you had to wear just one color for the rest of your life, what would it
be?
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250. Can you drive? If so, what kind of driver are you?
253. If you won the lottery, what would you do with all the money?
254. If you could have anything right now, what would it be?
257. If you were a cartoon character, what would your signature outfit be?