Sometimes, you meet someone, and you just click. You feel like you’ve been besties your entire life and honestly can’t believe there was a time when you didn’t even know they existed. And then, there’s those other relationships that take a little more work—i.e., how it feels like pulling teeth to learn anything about your brother-in-law. While you might never be BFFs with your BIL, there is a trick you can use to get him to open up a little more.
Terri Orbuch, PhD, author of 5 Simple Steps to Take Your Marriage from Good to Great, says getting to know someone starts with the “breadth questions”—think: impersonal but important biographical info about a person’s family, their career, and if they’re single or married, for example. (Although if you’re asking these q’s of your BIL… you should
probably definitely know the answer to that last one.)
Tamekis Williams, LCSW, founder of Mission Dorothy Female Empowerment Services, adds that you want to ask open-ended questions that will allow the other person to elaborate, instead of questions that can be answered with a simple “yes” or “no.”
After all, if you really want to get to know someone beyond the surface level, you’ve got to dig deeper. “Topics that get at the other person’s inner world—their thoughts, goals, and dreams—will strengthen and increase bonding between two people,” Orbuch notes. “Sharing personal information strengthens any relationship, and deeper questions focus on that personal self-disclosure.”
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Btw, that’s a two-way street, adds Williams. “When initially meeting someone, it is important to be inviting and warm so that the other person can initially feel comfortable talking with you.”
On that note, Williams suggests taking a careful approach in your questions, as you don’t want the other person to feel like you’re violating their privacy. Questions you should probably steer clear of early on: “Democrat or Republican?” “Do you own or rent?” and “What is your faith or spiritual belief?”.
There are other ways to bypass small talk and learn more in-depth info about the other person, says Williams. “You can get the answers [you’re looking for] by sometimes answering those questions yourself while sharing about you. An example would look like: ‘I just moved to Georgia last year and found a beautiful community that I fell in love with and purchased a home. What about you, do you love where you live?'”
With a little patience, you’ll become way closer with the person you’re just getting to know in no time. Here are 200 not-boring questions to get you started:
“Asking someone about their preferences helps you to understand who they are as a person,” says Rebecca Hendrix, 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.
Some other ideas:
1. What’s your favorite way to spend a day off?
2. What type of music are you into?
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?
6. What was your favorite age growing up?
7. Was the last thing you read?
8. Would you say you’re more of an extrovert or an introvert?
9. What’s your favorite ice cream topping?
10. What was the last TV show you binge-watched?
11. Are you into podcasts or do you only listen to music?
12. Do you have a favorite holiday? Why or why not?
13. If you could only eat one food for the rest of your life, what would it be?
14. Do you like going to the movies or prefer watching at home?
15. What’s your favorite sleeping position?
16. What’s your go-to guilty pleasure?
17. In the summer, would you rather go to the beach or go camping?
18. What’s your favorite quote from a TV show/movie/book?
19. How old were you when you had your first celebrity crush, and who was it?
20. What’s one thing that can instantly make your day better?
21. Do you have any pet peeves?
Questions can help deepen any relationship, but you should never have to ask these ones if you’re in a healthy relationship:
22. Which meal is your favorite: breakfast, lunch, or dinner?
23. What song always gets you out on the dance floor?
24. When you were a kid, did you eat the crusts on your sandwich or not?
25. What activity instantly calms you?
26. Ideally, how would you spend your birthday?
27. What do you do on your commute to/from work?
28. Do you have a favorite type of exercise?
29. What’s your favorite season and why?
30. What’s the best joke you’ve ever heard?
31. What’s the phone app you use most?
32. Would you rather cook or order in?
33. Have your ever disliked something and then changed your mind?
34. What’s your favorite board game?
35. How do you take your coffee?
36 What’s your most prized possession and why?
37. Is there any product that you couldn’t live without?
38. Do you sleep with a top sheet? Why or why not?
39. If you could have any exotic animal as a pet, which would it be?
40. What would be the first thing you’d do if you won the lottery?
No matter how a person feels about his or her 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.
Try out these convo-starters:
41. What’s your favorite thing about your current job?
42.What annoys you most?
43.What’s the career highlight you’re most proud of?
44.Do you think you’ll stay in your current gig awhile? Why or why not?
45.What type of role do you want to take on after this one?
46.Are you more of a “work to live” or a “live to work” type of person?
47.Does your job make you feel happy and fulfilled? Why or why not?
48. How would your 10-year-old self react to what you do now?
49. What do you remember most about your first job?
50. How old were you when you started working?
51. What’s the worst job you’ve ever had?
52. What originally got you interested in your current field of work?
53. Have you ever had a side hustle or considered having one?
54. What’s your favorite part of the workday?
55. What’s the best career decision you’ve ever made?
56. What’s the worst career decision you’ve ever made?
57. Do you consider yourself good at networking?
58. What career advice would you give to your younger self?
59. Do you believe in having a “five-year plan”?
60. How do you separate your work life from your home life?
61. When will you know you’ve “made it”?
62. Are you looking forward to retiring, or do you plan to work as long as possible?
63. Have you ever had “imposter syndrome”?
64. What do you think about workaholics?
65. What qualities do you look for in a boss?
66. Do you have a professional mentor? If not, do you want one?
67. Do you have a work best friend?
68. Are you into after-work happy hours?
69. How do you motivate yourself in your career?
70. What’s the best career advice you’ve ever heard?
71. What’s the worst career advice you’ve ever received?
72. When you started your current job, what most surprised you?
73. How do you pick yourself back up after making a mistake at work?
74. How do you deal with work stress?
75. What energizes you about your career?
76. What’s one work-related thing you want to accomplish in the next year?
77. Who has had the biggest impact on your career choice?
78. What does your family think of your career?
79. What’s the best thing you’ve learned in your current position?
80. If you could do it all over again, would you pursue the same career? Why or why not?
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:
81. How much time do you spend with your family?
82.Who do you most like spending time with and why?
83.Were you close with your family growing up?
84.How do you define your family now?
85.What traits are most important to you in your family members?
86.Who are you the closest to and why?
87.Do you want a family of your own?
88. What’s your favorite family tradition?
89. If you could change your relationship with a family member, would you? If so, with whom?
90. What was it like growing up as the youngest/oldest/middle/only child?
91. Does your family ever take trips together?
92. What’s your favorite family memory?
93. What TV family most reminds you of your own?
94. Do you ever wish you were raised differently?
95. What’s the best piece of advice a family member has given you?
96. Do you wish you had more siblings? If so, why?
97. Did you ever hide anything from or lie to your parents?
98. If you had a family business, what would it be?
99. Do you and your family have any nicknames for each other?
100. What’s your favorite way to spend time with your family?
101. How do you show your family you love them?
102. Have you ever been to a family reunion?
103. What’s the most important holiday you spend with your family and why?
104. Who in your family would you describe as a “character”?
105. How do you feel about family events?
106. What’s something your family would be surprised to learn about you?
107. Which family member do you confide in most?
108. How do you deal with arguments between family members?
109. If you have children, how do you want to raise them?
110. What’s more important: family or friends?
Questions about close relationships can lead to stories, and sharing stories leads to connection.
111. Do you have any friends you would consider family?
112. Has your family ever pressured you to act a certain way?
113. Did you ever get to meet your great-grandparents?
114. What personality traits do you share with your relatives?
115. What physical traits do you share with your relatives?
116. What stories did your family members tell you growing up?
117. How did your parents (and/or grandparents) meet?
118. What makes you proud of your family?
119. Who’s the newest member of your family?
120. What can always bring your family together?
“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. What makes you feel at peace?
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. Would you rather make more money doing a job you hate or less doing one you love?
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 has your perspective on the world changed over time?
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. Are you active on social media, or do you prefer to be more private?
145. Do you volunteer at all?
144. Are you an organ donor, and how did you come to that decision?
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?
158. Which famous person in history would you want to spend the day with?
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?
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:
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?
“Anytime you reveal personal information to someone else, it increases intimacy between you and the other person.”
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 about something mundane?
185. Do you “stan” any celebrities?
186. What’s your go-to midnight 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 (and answer!) these deep questions.
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