Ways to use this list
- Long walks with a friend: draw one question at the start and let it fill the whole walk. Deep questions need time, not speed.
- Family dinner with teenagers: Gentle starters work better than a direct "how are you really?" and give everyone an easy way in.
- Journaling at bedtime: draw a Really deep question, write for ten minutes, then read your answer again in a month.
- Partners or old friends catching up: take turns, and whoever draws the card answers first so nobody feels put on the spot.
- Youth groups and sixth-form tutor time: show the card on the board and let each person choose to answer, pass or ask a question back.
Press Draw a card, tap the game or press the Space bar. Change the list in the box as you
like: add your own, delete what doesn't suit you, or write *2 after an entry to give it double the
chance. The game buttons switch the same list to a wheel, duck race, hat and more.
The full list (36 entries)
- What does a good life look like to you?
- When do you feel most like yourself?
- What is a lesson that took you a long time to learn?
- Who has shaped the way you see the world?
- What are you proud of that few people know about?
- What is a fear you have overcome?
- What would you do if you knew you could not fail?
- What have you changed your mind about?
- What does friendship mean to you?
- What is a memory you would love to live again?
- What do you wish more people understood about you?
- Which small moments make you happiest?
- What would you tell your younger self?
- What is the kindest thing someone has done for you?
- What does home mean to you?
- What would you like to be remembered for?
- What is a dream you have not told many people?
- How do you know when you need a rest?
- What is something you are still learning to accept?
- What makes you feel brave?
- What is a habit you would like to build?
- When was the last time you surprised yourself?
- What does success mean to you?
- What is a tradition you want to keep forever?
- What is something you are grateful for today?
- How have you changed in the last five years?
- What do you value most in the people around you?
- What would your perfect ordinary day look like?
- What is a hard thing you are glad you did?
- What gives you hope?
- Who do you need to thank but have not yet?
- What did a mistake teach you?
- Which piece of advice changed the way you live?
- What would you do with a whole year off?
- What do you hope never changes about you?
- What is something small you are looking forward to?
📖 Related guide: Who goes first? 12 fair ways to decide
Questions people ask
What are good deep questions to ask someone?
Questions about values, turning points and hopes rather than facts: what a good life looks like to them, what they would tell their younger self, who shaped how they see the world. Open questions like these invite stories.
How do you ask deep questions without it feeling awkward?
Start with a gentle question, answer it yourself first, and leave silences alone; people often need a few seconds to think. Drawing a card also helps, because the question comes from the deck, not from you.
Are these deep questions suitable for teenagers?
Yes. They avoid romance, religion and politics, and none of them asks for private details. Teenagers often prefer Gentle starters at first, then reach for the deeper ones once the group feels comfortable.
What if a question brings up something difficult?
Let the person pass, thank them for whatever they did share, and move on to a lighter card. Deep questions should open conversations, never force them.