Obscure questions to get to know someone

​Questions are a great way to start a conversation at a barbecue, a Zoom networking event, or a party.

Questions can even help you move past small talk and into deeper topics. (Which studies suggest could make you happier!)

If you’ve ever struggled with thinking up questions to get to know someone better, this post is for you! 

After your conversational partner responds, keep the conversation going by making an observation about what they said.

Look through the list below and copy/paste 5 of your favorite questions into the notes app on your phone.

Then, you’ll be all set to break the ice at your next social event!

Bonus Pro-tip: Check out this massive list of 300+ conversation starters and topics or this huge list of 170+ icebreaker questions if you need help sparking conversations!

Here are 179+ questions to get to know someone better...

1. Where are you from?
2. What are your hobbies outside of work?
   
3. What is one thing you are very good at?
   
4. What’s your story?
5. What has been the highlight of your week so far?
6. What brought you here?
7. Any upcoming travel plans you're excited about?
8. Are you into any podcasts right now?
9. What's your favorite hobby right now?
10. Are you typically early or late?
11. What could you give a 60-minute talk on with zero notice?
12. What’s your go-to after work drink?
13. What's keeping you busy these days?
14. Did you have a favorite pet growing up?
15. Did you start working right after finishing school?
16. Do you believe in fate?
17. Do you cook?
18. Do you have a favorite holiday?
19. Where is the most interesting place you’ve been?
20. Are you more of a "work to live" or a "live to work" kind of person?
21. Do you have a favorite type of exercise?
22. Do you have any hidden quirks?
23. Do you have any recurring dreams?
24. Does your job make you feel happy and fulfilled?
25. Have you ever had a side hustle?
26. What movie best describes your day?
27. What made you decide to do the work you're doing currently?
28. How different was your life 5 years ago?
29. How do you deal with people you don’t like?
30. How do you relax after a hard day at the office?
31. How do you separate your work life from your home life?
32. How often do you play sports?
33. If all jobs paid $200,000, what job would you want to have?
34. If someone were to play you in a movie, who would you want it to be?
35. What is one personal “rule” that you never break?
36. If you could have any superpower what would it be?
37. If you could live in any decade, what would it be?
38. If you could teach one thing to everyone, what would it be?
39. If you could win a medal for any sport, real or fake, what would it be?
40. If you had 1 billion dollars-what would your dream house look like?
41. If you never had to sleep, what would you do with all the extra time?
42. If you suddenly became a master at a skill, what would it be?
43. If you were King/Queen of a small nation, what crazy stuff would you do?
44. If you were planning a heist, who would be in your crew?
45. Is your job fulfilling?
46. Was the last thing you read?
47. What are you likely wrong about?
48. What are you looking forward to in the coming weeks?
49. What are you most likely to be famous for?
50. What are you most looking forward to in the next 5 years?
51. What are you reading currently?
52. Do you know what your communication style is? (If not - take the linked quiz and find out!)
53. What are you super interested in that most people have never heard of?
54. What awesome thing did you do that no one saw?
55. What big or small lifestyle change have you been meaning to make?
56. What is one event in your life that made you who you are today?
57. What book universe would you most like to live in?
58. What career advice would you give to your younger self?
59. What city would you want to move to?
60. Have you ever burned any bridges?
61. What do people usually come to you for help with?
62. What do you consider to be your best garage sale find?
63. What do you hope never changes?
64. What do you listen to on your commute to work?
65. What was your first job like?
66. What do you think everyone should try once?
67. What do you think is the best way a person can spend their time?
68. What everyday activity would you turn into a professional sport?
69. What fictional movie/TV universe would you most want to live in?
70. What hobby have you always wanted to get into?
71. What is a small thing that makes your day better?
72. What is one possession you can’t live without?
73. What is one thing no one realizes about you?
74. What is one thing that people wouldn’t believe was true about you?
75. What is one thing you want to be remembered for?
76. What is one thing you wish you could go back and re-do?
77. What is something challenging that you're working through right now?
78. What is something that a lot of people love, but you just don’t get?
79. What is something you think people should see at least once in their lives?
80. What is something you’ve had to unlearn?
81. What is the best compliment you’ve ever received?
82. What is the luckiest thing that has ever happened to you?
83. What is the most impressive thing you know how to do?
84. What is the most wholesome thing you’ve ever seen?
85. What is the one thing you spend the most time thinking about?
86. What is the worst decision you’ve ever made?
87. What is your favorite city?
88. What is your favorite lyric from a song?
89. What is your favorite piece of clothing you've ever owned?
90. What is your favorite quality?
91. What is your favorite type of movie?
92. What is your hidden talent?
93. What is your least favorite food?
94. What is your most-used emoji?
95. What is your newest opinion?
96. What job do you think you’d be amazing at?
97. What job would you not be good at?
98. What kind of art do you like?
99. What makes you laugh no matter what?
100. What movie best describes your life?
101. What movie or TV show do you wish you could delete from your memory so that you watch it for the first time again?
102. What one experience you really want but can’t afford yet?
103. What originally got you interested in your current career?
104. What place do you never want to go back to?
105. What question do you wish you knew the answer to?
106. What question would you most like to know the answer to?
107. What shows are you watching right now?
108. What skill would you love to master?
109. What song automatically gets you out on the dance floor?
110. What song do you know by heart?
111. What surprises you the most about people?
112. Who is your most interesting friend?
113. What takes up your time?
114. What thing are you absolutely determined to do?
115. What thing do you wish you knew more about?
116. What thought keeps you up at night?
117. What trend do you hope never comes back?
118. What TV show or movie do you flat-out refuse to watch?
119. What type of music are you into right now?
120. What type of job do you want to move to after this one?
121. What was the best book that you’ve ever read?
122. What was the best vacation you ever took?
123. What was the last show you binged on Netflix?
124. What was the most meaningful gift you’ve received?
125. What was your favorite subject in high school?
126. What was your favorite class in college?
127. What would be your dream car?
128. What would be your first question after time traveling ahead 100 years?
129. What would be your ideal way to spend the weekend?
130. What would you rate 5/5 stars?
131. What would you tell your 21 year old self?
132. What would your perfect birthday be like?
133. What YouTube channel doesn’t exist but totally should?
134. What's one small thing that can magically make your day better?
135. What's one thing on your bucket list that you've crossed off?
136. What's one thing on your bucket list?
137. What's special about the place where you grew up?
138. What's the best Halloween costume you've ever had?
139. What's the last song you added on Spotify?
140. What's your dream job?
141. What's your favorite 90’s show?
142. What's your favorite college story?
143. What's your favorite kind of ice cream?
144. What's your favorite season?
145. What’s something you'd rather do the old-school way?
146. What’s something you’ve been meaning to do but just haven’t yet?
147. What’s the best thing that happened to you yesterday?
148. What’s the best way to start the morning?
149. What’s the career highlight you’re proud?
150. What’s the farthest you’ve ever traveled from home?
151. What’s the first concert you attended?
152. What’s the hardest career choice you’ve ever made?
153. What’s the most bravest thing you’ve ever done?
154. What’s the most exciting thing in your life right now?
155. What’s TV show/movie/book do you quote most often?
156. What’s worth spending more money on to get the best?
157. What’s your all time favorite meal?
158. What’s your favorite app?
159. What’s your favorite board game?
160. What’s your favorite book?
161. What’s your favorite day on the calendar?
162. What’s your favorite guilty pleasure?
163. What’s your favorite thing about your current job?
164. What’s your favorite type of book or movie?
165. What’s your favorite way to spend a three day weekend?
166. When is the last time you felt really happy?
167. When was the last time you changed your opinion on something big?
168. When was the last time you left the house without your phone?
169. Where do you usually go when you have a day off?
170. Where is the most relaxing place you’ve ever visited?
171. Where would you be all the time if you could?
172. Where’s the next place you want to travel?
173. Which is your favorite: breakfast, lunch, or dinner?
174. Who has impressed you most with what they’ve accomplished?
175. Who is a historical figure you would like to have a beer with?
176. Who's your favorite superhero?
177. Would you change anything about your family?
178. Would you rather go sky-diving or bungee jumping ?
179. Would you say you’re an extrovert or an introvert?
180. What’s your Enneagram type?
181. What's something that you've always wanted to do, but havent?
182. What is your go-to Karaoke song?
183. What song or album could you listen to on repeat?
184. Why is the best movie Back to the Future?

Wow...That was a LOT of questions!

If you can’t think of any good questions to ask to get to know someone after that list...I don’t know what to tell you.
​
Again, choose 5 and copy/paste them into the notes app on your phone so you’ll have some good questions ready next time you need them!

Also: If you want to learn how to have better conversations, check out this video:

Pro Tip: Use “Dig Questions” to go deeper with people!

Yeah, a huge list of questions is great, but what happens after they answer?

It’s important to be able to go deeper with people in conversation.

If you’re trying to get to know someone better, try asking one of these follow up questions:

• "Tell me more about x."
• "Why x? What’s the story there?"
• "What was that moment like for you?"
• "When did you first realize x?"
• "Knowing what you know now, would you have still done x?"

Give them space to share more with you. This will help them open up, and will help you both find similarities.

(Just be sure to balance out the questions with a stories, observations and talking on your side or they’re going to start feeling interrogated.)

Pro-tip: Don’t ONLY ask questions.

Conversation is a two-way street.

With conversations, there are very few hard and fast rules.

However, you should try to balance questions you ask and observations you give.

If we ask too many questions, we'll fall into the "interrogation trap". (We don't want the other person feeling like they are being interviewed!)

On the other hand, if we only make observations, then it can feel like we're just talking at them rather than talking with them.

So how do we find the right balance?

Start by asking open-ended questions instead of yes/no questions or ones that can be answered with one word or phrase.

​Then, mix in some observations.

Here's what that might look like in practice:

Ted: "This week has been crazy. I worked 42 hours on one project. When I close my eyes, I see spreadsheets!"

You: "Wow! You must be really dedicated to getting stuff done!"

Here, you were able to pay Ted a compliment while making an observation about his statement.

This leads to the two-way street of conversation where there is a sense of give and take between people.

Next Step: Improve your group conversations!

Want more tips to help you supercharge your people skills?

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​I'll send you my free 56-minute audio guide on joining and enjoying group conversations. (As well as Q&A videos, podcast, and much more)

In the audio guide, you’ll learn…

• How to jump into a conversation that has no opening
• Genuinely Connect With Anyone About Any Topic
• How To Get Out Of Your Head And Stay Present In Group Conversations
• And more (word-for-word scripts, body language while joining a group, etc)

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