Questions
Cocktail Party Questions
For better chats with new people
What was your first job?
What’s your favorite way to spend a completely free day?
What is the most relaxing part of your morning or evening?
What’s a dish you loved as a child?
What’s a rule you had growing up that, looking back, you now think was totally unnecessary or even a little funny?
What’s one thing life is teaching you right now?
What’s something you believe you have a talent for, but would never turn into a profession?
If you were going back to school to study something different from your degree, what would it be and why?
Vacation Questions
To deepen relationships
What crossroads are you at?
If we meet a year from now, what will we be celebrating?
If the next five years is a chapter in your life, what is that chapter about?
What’s working really well in your life?
What are you most self-confident about?
What has become clearer to you over time?
What is a quality in other people that immediately makes you trust them?
What does “success” mean to you right now?
What could you give a 10 minute lecture about with no prep?
Question sources: Priya Parker, Alison Wood Brooks, David Brooks, Peter Block
Brooks, D. (2023). How to know a person: The art of seeing others deeply and being seen deeply. Random House.
Catron, M. L. (2015, January 9). To fall in love with anyone, do this (published 2015). The New York Times. https://www.nytimes.com/2015/01/11/style/modern-love-to-fall-in-love-with-anyone-do-this.html
Duhigg, C. (2024). Supercommunicators: How to unlock the secret language of connection. Random House.
Gharib, M., Segarra, M., & Yellowhorse Kesler, S. (2025, May 29). Want to cut through small talk? Try asking a “magical question.” NPR. https://www.npr.org/2025/05/29/nx-s1-5355077/want-to-cut-through-small-talk-try-asking-a-magical-question
McNerney, S. (2025, September 17). A good survey question is a flashlight, not a floodlight. Sam McNerney. https://www.sammcnerney.com/newsletter-new/a-good-survey-question-is-a-flashlight-not-a-floodlight
Parker, P. (2020). The art of gathering: How we meet and why it matters. Riverhead Books.
Wood Brooks, A. (2026). TALK Sparks. TALK Studios. https://www.talkstudios.com/talk-sparks
Zhou, H., Majka, E. A., & Epley, N. (2017). Inferring perspective versus getting perspective: Underestimating the value of being in another person’s shoes. Psychological Science, 28(4), 482–493. https://doi.org/10.1177/0956797616687124
References: Questions for Connection
