to know another person

33 questions for generative social space

As a facilitator of creative and contemplative experiences, I’ve designed quite a few games for teams. One of my favorites for building connection was inspired by an article called 36 Questions that Lead to Love. I also have a soft spot for Esther Perel’s question-driven card game Where Should We Begin? and Warren Berger’s Book of Beautiful Questions.

Good questions—and by ‘good’ I mean those that help us see differently—are accelerators of intimacy with oneself, the world, and others. I’ve gamified questions in settings where the norm is to NOT see people as multi-dimensional but instead to see them as a role, but this is humanity reduced to mechanics and very few people truly want that. As good question games warm up, something wonderful and reliable happens: the barriers between people start to soften and they remember the fullness of another’s humanity. Even if it’s just for a brief interlude, participants become more receptive to each other—slightly less preoccupied with reinforcing identifies and slightly more enchanted by the relationship, the energy and information that flows between. Good questions create that elusive, expansive, and emergent WE. It is a sight to behold.

Because in this state of un-selfing and we-making, social experiences then become generative—bursting with the chance to discover, unlearn, co-create, and connect. As a facilitator, it’s heartening to witness this unfold so I wanted to share 33 good questions¹ to help you ignite a relational field. Pick one—at least one!—and ask it of someone today. I can assure you that if you ask sincerely and listen closely—listen with ears, eyes, and an undivided heart—you will see things differently. You might even make a new friend.

Off you go!

1. Who made you feel seen when you were growing up?

2. What major event or realization shaped who you are?

3. Imagine yourself in spirit form with boundless abilities. What gift would you want to offer the living?

4. Of all the living people you’re no longer in touch with, who is the person with whom you were the closest? Why aren’t you in touch anymore?

5. When did you realize you were a grown-up?

6. If you had more than enough money to meet your needs, what would you do with your time?

7. When you were a kid, what did you find exciting about the prospect of getting older?

8. What’s something you swore you’d never do but did anyway?

9. What is life teaching you right now?

10. What’s the worst advice you’ve ever received?

11. What’s the worst advice you received that you actually followed?

12. What’s a phrase or mantra that has kept you afloat during hard times?

13. Thinking back over the past few decades, what advice would you offer for people growing up today?

14. What is one of your favorite memories?

15. What’s a unique experience you’ve had that you wish someone else could have?

16. Name a specific moment in life that you didn’t know how to handle. What did you end up doing?

17. What is something you’ve learned about yourself in the last six months?

18. What is one thing you must do with someone else that you should start planning for now?

19. If a part of you needed to hear something encouraging today, what would you say to that part?

20. Tell me about a difficult emotion you’ve been dealing with lately and what you do with it.

21. Is there anything you do that seems mundane on the surface but has turned
    out to be sacred for you?

22. What’s something you still haven’t figured out? What are you still wondering about?

23. What makes spending time together meaningful for you?

24. Aside from rich, famous or successful people, whose shoes would you want to walk in and why?

25. Did you have any nicknames when you were younger? What’s the story behind them?

26. What was your favorite game growing up and why?

27. Can you tell the story of another person that made a lasting impression on you?

28. If you created a time capsule and you had to choose one item to include for future humans, what would that item be, and why?

29. What do you hope happens when we die?

30. Name some of the most memorable songs in your life, and share what they
    mean to you.

31. What book changed your life when you were a kid?

32. If you could redo any period in your life, what would it be, and why?

33. What is your favorite compliment to receive, and why?

1. Many of these questions are from the NY Times piece 25 Questions to Bring You Closer to Your Mom, and some are from my imagination and the imagination of others.