Deep Conversations

Questions about fears, regrets, identity and what really matters. Best when you have time, privacy and a bit of courage.

Questions: 40
Light: 6
Medium: 14
Deep: 20

A taste of the deck

Light
What's a small thing that makes an ordinary day feel meaningful?
Medium
What's a fear you've outgrown?
Deep
What's your biggest fear about the future?

See all 40 questions

Light

What's a small thing that makes an ordinary day feel meaningful?
What's a question you wish people asked you more often?
What are you grateful for that you rarely say out loud?
What song says something you struggle to put into words?
When do you feel most at peace?
What's a simple pleasure you'd never give up?

Medium

What's a fear you've outgrown?
What's a mistake that taught you more than any success has?
What does success mean to you now, compared with five years ago?
Which do you trust more when it matters: your head or your gut?
What's something you've finally forgiven yourself for?
What role do you play for other people that sometimes feels heavy?
What conversation changed the direction of your life?
Is there someone you still owe a thank you?
What do you think you're here to do?
What do you pretend not to care about but secretly do?
How do you usually cope when things fall apart?
What's an opinion you hold that you're not sure is right?
What part of your past have you made peace with?
What would you do differently if nobody was watching or judging?

Deep

What's your biggest fear about the future?
What's a regret you're still carrying?
When did you last cry, and what was it about?
What's something you've never told anyone in this room?
What do you think people misunderstand most about you?
What does love look like when it isn't easy?
If you knew you couldn't fail, what would you be doing differently?
What's the hardest thing you've ever had to let go of?
What belief has carried you through a hard time?
Which part of yourself do you hide the most?
If you could ask your future one question, what would it be?
What do you need but find hard to ask for?
How do you want to be loved when you're at your worst?
What's a version of yourself you had to say goodbye to?
When have you felt most alone, and what helped?
What are you still a little angry about?
What does being brave look like in your everyday life?
If you could sit down with your younger self, what would you say first?
What's the kindest thing someone did for you when you needed it most?
What do you hope you'll have figured out by the end of your life?

Game setup

All optional. The defaults work well.

Question depth

Session length

Play style

One person reads, everyone answers.