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Deep questions to ask when small talk runs out

Good deep questions are specific. "What's a choice that quietly changed everything after it?" gets a real story, where "What's the meaning of life?" gets a shrug. Every list below is free to read, and each one plays live: the screen shows a question and picks who answers.

  • 125 questions
  • 5 lists
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Deep questions for a real conversation

Thirty starters that work with almost anyone, from a new friend to a parent.

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  1. 01What's something you believed as a kid that you still kind of believe?
  2. 02When do you feel most like yourself?
  3. 03What's a moment that changed the direction of your life?
  4. 04What are you most grateful for right now?
  5. 05What does a good life look like to you?
  6. 06What's something you've forgiven someone for?
  7. 07What's a fear you've overcome?
  8. 08What would you tell your 15-year-old self?
  9. 09What do you want people to remember about you?
  10. 10What's something you're still figuring out?
  11. 11Who has shaped you the most, and how?
  12. 12What's a risk you're glad you took?
  13. 13What's a risk you wish you had taken?
  14. 14When did you last change your mind about something important?
  15. 15What does friendship mean to you now compared to ten years ago?
  16. 16What's something you wish more people asked you about?
  17. 17What's a small moment you'll never forget?
  18. 18What makes a place feel like home to you?
  19. 19If you could know one thing about your future, what would you want to know?
  20. 20What's a belief you hold that most people around you don't?
  21. 21What's the hardest thing you've ever had to say to someone?
  22. 22What does success mean to you today?
  23. 23What part of yourself took you the longest to accept?
  24. 24What would you try if you knew you couldn't fail?
  25. 25What do you think you're meant to do?
  26. 26What's a lesson you keep having to learn again?
  27. 27What's the kindest thing anyone has ever done for you?
  28. 28How do you want to grow in the next year?
  29. 29What's something you miss that you can't get back?
  30. 30What do you wish you heard more often from the people you love?

Deep questions about life

Time, luck, regret and what a good life looks like.

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  1. 31If you knew you had ten years left, what would you stop doing tomorrow?
  2. 32What do you think you're here to do?
  3. 33Is it better to be happy or to be interesting?
  4. 34What's a choice you made that quietly changed everything after it?
  5. 35Which do you trust more, your gut or your head?
  6. 36What would you want people to say about you when you're not in the room?
  7. 37What does success look like to you now, compared with ten years ago?
  8. 38What's something you've stopped being afraid of?
  9. 39When was the last time you changed your mind about something big?
  10. 40What's one thing you hope never changes about you?
  11. 41Do you think people really change, or just get better at hiding things?
  12. 42What's the kindest thing a stranger ever did for you?
  13. 43What part of your life would you most like to live again, exactly the same?
  14. 44Is there a question you're afraid to know the answer to?
  15. 45What would you do differently if nobody could judge you for it?
  16. 46What's a lesson you had to learn twice?
  17. 47What do you owe the people who raised you?
  18. 48If your life had a theme song right now, what would it be and why?
  19. 49What's something small that makes your day better every single time?
  20. 50Which mistake taught you the most?
  21. 51What does home mean to you?
  22. 52What are you still trying to prove, and to whom?
  23. 53Would you rather know the date you die or how you die?
  24. 54What's a rule you live by that you made up yourself?
  25. 55When do you feel the most at peace?
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Deep questions to ask your friends

For friends who already know the surface stuff.

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  1. 56What's something you've never told me because you thought I'd judge you?
  2. 57When did you first feel like we were real friends?
  3. 58What's a hard year you got through that I didn't know was hard?
  4. 59What's one thing you wish I asked you about more?
  5. 60Which of your friendships has changed the most, and why?
  6. 61What do you think I'm better at than I give myself credit for?
  7. 62What's a dream you gave up on, and do you miss it?
  8. 63What do you need more of from the people around you?
  9. 64Who do you call when something goes really wrong?
  10. 65What's your biggest fear about the next five years?
  11. 66What's something you're proud of that nobody ever congratulated you for?
  12. 67When do you feel most misunderstood?
  13. 68What's the best advice you've ignored?
  14. 69What's something about me you'd defend to anyone?
  15. 70If we met today, do you think we'd still become friends?
  16. 71What's something you're still healing from?
  17. 72What does a good friend do that most people forget?
  18. 73Which version of yourself do you miss?
  19. 74What's the bravest thing you've ever done?
  20. 75What would you do with a whole year off, no money worries?
  21. 76What's a topic you could talk about for hours?
  22. 77What part of growing up hit you hardest?
  23. 78What's one thing you'd change about how you were raised?
  24. 79When was the last time you cried, and why?
  25. 80What should we do together before we're too old to do it?

Philosophical questions

No right answers, which is the point. Save these for the end of a long dinner.

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  1. 81If you could know the absolute truth to one question, what would you ask?
  2. 82Is a lie ever kinder than the truth?
  3. 83Would you plug into a machine that gave you a perfect, happy life if none of it was real?
  4. 84Do we have free will, or does it only feel that way?
  5. 85If you replaced every part of a boat one at a time, is it still the same boat?
  6. 86Is it possible to be completely selfless?
  7. 87What makes a person the same person over a whole lifetime?
  8. 88Would you want to live forever if everyone you loved didn't?
  9. 89Is it wrong to break a rule nobody will ever find out about?
  10. 90Does the end justify the means if the end is good enough?
  11. 91Are we more defined by what we do or by what we don't do?
  12. 92If you could erase one memory, would you, knowing it made you who you are?
  13. 93Can you be happy without ever being sad first?
  14. 94Is it better to have loved and lost, or never loved at all?
  15. 95What do you think happens after we die?
  16. 96Would you rather be remembered or be good?
  17. 97If animals could talk, which would be the rudest?
  18. 98Is there a difference between being alone and being lonely?
  19. 99Can someone be a good person and still do a terrible thing?
  20. 100Is luck real, or is it just a word for things we can't explain?
  21. 101Would the world be better if everyone told the truth all the time?
  22. 102What's more important, being right or being kind?
  23. 103If you found out you were living in a simulation, would anything change?
  24. 104Does art need an audience to count as art?
  25. 105Is it braver to stay or to leave?

Deep questions to ask yourself

Reflection questions for a journal, a long walk or a fire pit.

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  1. 106What am I pretending not to know?
  2. 107What would I do if I weren't afraid of failing?
  3. 108Who do I envy, and what does that tell me about what I want?
  4. 109What drains me that I keep saying yes to?
  5. 110When did I last do something for the first time?
  6. 111What story about myself am I ready to stop telling?
  7. 112What do I want more of next year, and what do I want less of?
  8. 113Whose approval am I still chasing?
  9. 114What would my younger self think of my life right now?
  10. 115What's a compliment I can't accept, and why?
  11. 116Where do I spend my time, and does it match what I say matters?
  12. 117What would make this year feel like a good year?
  13. 118What do I do when nobody is watching?
  14. 119What am I most grateful for that I never say out loud?
  15. 120Which relationship needs more of my attention?
  16. 121What's one boundary I need to set?
  17. 122When do I feel the most like myself?
  18. 123What did I love doing as a kid that I stopped doing?
  19. 124What would I regret not trying?
  20. 125What do I need to forgive myself for?
How it works

Ready in about a minute

  1. 01

    Open the game on a TV, a laptop or a projector. The screen shows a six-digit code and a QR code.

  2. 02

    Everyone scans the QR or types the code at LivePartyGames.com. Nobody has to install an app or make an account.

  3. 03

    Every phone answers in secret, then the big screen shows what the room picked.

How to ask a deep question without it getting weird

Go first. Answering your own question shows how much to share, and it takes the pressure off. Ask one question, then follow up on the answer instead of jumping to the next one. The follow-up ("what happened after that?") is where the conversation gets good.

Past before future

Questions about what happened are easier than questions about what someone believes.

Let people pass

A pass is a fine answer. Move on and come back later.

Follow the answer

One good follow-up beats three new questions.

Playing deep questions as a group

In a group, the hard part is deciding who answers. The live game handles that: the question goes on the TV with one name under it, and that person answers out loud. Nobody gets picked twice in a row, and the host can skip anyone with one tap.

Questions

Good to know

What is a good deep question to ask?

One about a specific moment, like "What's a choice that quietly changed everything after it?" Specific questions get stories; vague ones get shrugs.

Are deep questions OK for a first date?

A few light ones are. Start with the conversation starters and save the philosophical ones for later dates.

Can I play these with a group?

Yes. Put a list on the TV and the game picks who answers each question. Everyone joins from their phone with a code, and nobody needs an app.

Keep reading

More ideas for the night

Questions to ask your friends First date questions Icebreaker questions

Get the party going tonight

Open it on the TV, share the code, and ask the first question in under a minute.

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