GOOD QUESTIONS. BETTER COMPANY.
30 deep talk questions for friends
You don’t need a grand occasion to ask a better question. On a rainy Vancouver evening, a long walk or the quiet end of a dinner, these prompts make space for the things everyday catch-ups can miss. Start with curiosity, listen without trying to fix everything, and let people share only what feels comfortable.
Play this deck ↗How to play
Choose a question, give everyone time, and listen. Don’t ask anyone to explain a pass. This is a conversation, not a test.
Every prompt is optional. No drinks or personal disclosures required.
Pick a question and go.
- 01
What makes you feel at home, wherever you are? Passing is welcome.
Take a turn, share if you want to, or pass.
- 02
What kind of support helps you most? You can pass.
Take a turn, share if you want to, or pass.
- 03
Which small tradition would you like to start? Or pass.
Take a turn, share if you want to, or pass.
- 04
What has friendship taught you recently? Passing is welcome.
Take a turn, share if you want to, or pass.
- 05
When do you feel most like yourself? You can pass.
Take a turn, share if you want to, or pass.
- 06
What's something you're learning to be patient with? Or pass.
Take a turn, share if you want to, or pass.
- 07
What would a kinder week look like for you? You can pass.
Take a turn, share if you want to, or pass.
- 08
Which compliment stayed with you? Passing is welcome.
Take a turn, share if you want to, or pass.
- 09
What does rest mean to you beyond sleep? Or pass.
Take a turn, share if you want to, or pass.
- 10
What’s a boundary you're glad you learned? You can pass.
Take a turn, share if you want to, or pass.
- 11
What do you want more time for? Passing is welcome.
Take a turn, share if you want to, or pass.
- 12
Which memory makes you feel quietly proud? Or pass.
Take a turn, share if you want to, or pass.
- 13
What helps you feel heard? You can pass.
Take a turn, share if you want to, or pass.
- 14
What’s a belief you've gently changed your mind about? Or pass.
Take a turn, share if you want to, or pass.
- 15
How has your idea of a good day changed? You can pass.
Take a turn, share if you want to, or pass.
- 16
What makes a friendship feel safe to you? Passing is welcome.
Take a turn, share if you want to, or pass.
- 17
What’s a tiny thing you want to celebrate today? Or pass.
Take a turn, share if you want to, or pass.
- 18
Which place would you love to revisit with friends? You can pass.
Take a turn, share if you want to, or pass.
- 19
What are you curious about right now? Passing is welcome.
Take a turn, share if you want to, or pass.
- 20
What do you wish people asked you more often? Or pass.
Take a turn, share if you want to, or pass.
- 21
Would you rather have more free time or more creative energy?
Choose one, then tell the group your reason.
- 22
Would you rather build a new tradition or revive an old one?
Choose one, then tell the group your reason.
- 23
Would you rather receive practical help or a long listening session?
Choose one, then tell the group your reason.
- 24
Would you rather learn from a mentor or teach a beginner?
Choose one, then tell the group your reason.
- 25
Would you rather preserve one perfect day or create a new adventure?
Choose one, then tell the group your reason.
- 26
Friendship can thrive without daily messages. What's your take?
Take a turn, share if you want to, or pass.
- 27
Changing your mind is a strength. Share a gentle example.
Take a turn, share if you want to, or pass.
- 28
Rest doesn't have to be earned. What do you think?
Take a turn, share if you want to, or pass.
- 29
Small acts of care matter more than grand gestures. Discuss.
Take a turn, share if you want to, or pass.
- 30
Being known is different from being understood. What’s your take?
Take a turn, share if you want to, or pass.