Deep questions for conversations that matter

Gentle ways in

Reflective but warm. A good place to start before anything heavier.

1. 1.What's a small thing that makes an ordinary day feel meaningful?
2. 2.What's a question you wish people asked you more often?
3. 3.What are you grateful for that you rarely say out loud?
4. 4.What song says something you struggle to put into words?
5. 5.When do you feel most at peace?
6. 6.What's a simple pleasure you'd never give up?
7. 7.What's a fear you've outgrown?
8. 8.What's a mistake that taught you more than any success has?
9. 9.What does success mean to you now, compared with five years ago?
10. 10.Which do you trust more when it matters: your head or your gut?
11. 11.What's something you've finally forgiven yourself for?
12. 12.What role do you play for other people that sometimes feels heavy?
13. 13.What conversation changed the direction of your life?
14. 14.Is there someone you still owe a thank you?

Questions about fear, regret and courage

For when you both feel safe enough to be honest.

15. 15.What's your biggest fear about the future?
16. 16.What's a regret you're still carrying?
17. 17.When did you last cry, and what was it about?
18. 18.What's something you've never told anyone in this room?
19. 19.What do you think people misunderstand most about you?
20. 20.What does love look like when it isn't easy?
21. 21.If you knew you couldn't fail, what would you be doing differently?
22. 22.What's the hardest thing you've ever had to let go of?
23. 23.What belief has carried you through a hard time?
24. 24.Which part of yourself do you hide the most?
25. 25.If you could ask your future one question, what would it be?
26. 26.What do you need but find hard to ask for?
27. 27.How do you want to be loved when you're at your worst?
28. 28.What's a version of yourself you had to say goodbye to?

Questions about who you are

From the Getting to Know You deck: identity, family and the stories that shaped someone.

29. 29.What's something about your upbringing you only appreciated later?
30. 30.What's a turning point in your life that most people don't know about?
31. 31.When was the last time you surprised yourself?
32. 32.What's a part of your personality you had to grow into?
33. 33.What are you proud of that took a long time to achieve?
34. 34.Who do you miss that you don't talk about much?
35. 35.What's a version of your life you sometimes wonder about?
36. 36.What used to embarrass you about yourself that you now love?
37. 37.What belief did you inherit that you've had to rethink?
38. 38.What does your inner voice sound like on a bad day?
39. 39.What do you want people to remember about you?

Making deep conversations feel safe

Anyone can pass

Say it out loud before you start. Knowing you can skip a question makes people more willing to answer the next one.

Listen more than you fix

Deep answers aren't problems to solve. A simple "thank you for telling me" often means more than advice.

Go in both directions

Take turns answering. Vulnerability lands better when it's shared.

Frequently asked questions