Deep questions to ask
Good deep questions to ask are open, honest and impossible to answer with yes or no, like "What's a lesson you had to learn twice?" or "Is love a feeling or a decision?" Here are 120 of them in eight groups: life, values, love, regrets and growth, the future, friendship, your partner and late at night.
What part of your childhood still shapes how you live today?
One question can easily fill half an hour, so there's no need to rush to the next card. All 120 questions are also listed below.
Tap the card to draw one question at a time, which takes the pressure off choosing. Switch on only the groups that fit who you're with, whether that's your significant other, your best friend or someone you want to know better.
- Questions
- 120
- Groups
- 8
- Best with
- 2 to 5 people
120 deep questions to ask
Life and The future are the gentlest way in. Values and Regrets and growth need a bit of trust. Your partner is for the person you're with, Friendship for a close friend, and Late night is for when everything else has gone quiet.
Deep questions about life
15- What part of your childhood still shapes how you live today?
- When did you last change your mind about something important?
- If one year of your life was a book chapter, which year, and what's the title?
- What's something you believed at 18 that you've let go of?
- What do you want your life to feel like, rather than look like?
- What's the hardest thing you've ever done that nobody saw?
- What's a small moment you'd like to relive exactly as it was?
- What does home mean to you now, compared to when you were a kid?
- When was the real turning point in your life so far?
- What are you still trying to prove, and to whom?
- What's a lesson you had to learn twice?
- Who are you when nobody needs anything from you?
- What have you survived that you don't give yourself credit for?
- When do you feel time moving the slowest?
- What do you think you are here to do?
Deep questions about values
15- What would you never do, even for a lot of money?
- Which of your values has cost you something?
- What makes someone a good person, in your opinion?
- Is it ever right to lie to someone you love?
- What do you respect most in other people?
- What's a rule you live by that you made up yourself?
- Where do you draw the line between honesty and kindness?
- What's something you think the world gets badly wrong?
- What would you stand up for in public, even if it cost you?
- Which of your parents' values did you keep, and which did you drop?
- Does success mean the same to you now as it did five years ago?
- What do you forgive easily, and what do you never forgive?
- What does the way you spend money say about what you care about?
- Is it more important to you to be respected or to be liked?
- What's a belief you hold that most of your friends don't?
Deep love questions to ask
15- How do you know when you love someone?
- What did your parents' relationship teach you about love?
- What's the most loving thing you've seen one person do for another?
- Do you believe there's one right person for everyone?
- How do you show love when words don't come easily?
- What does feeling safe with someone look like for you?
- Which love song do you think tells the truth?
- Can two people love each other and still be wrong for each other?
- What's the hardest part of letting someone really know you?
- What did your first heartbreak teach you?
- Is love a feeling or a decision?
- When you're struggling, do you need more space or more closeness?
- Which couple you know do you admire, and why?
- What will you never compromise on in a relationship?
- What's the bravest thing you've ever done for love?
Deep questions about regrets and growing up
15- What's a chance you didn't take that you still think about?
- What would you tell yourself the night before your hardest day?
- Who do you owe an apology you've never given?
- What mistake turned out to be one of the best things that happened to you?
- When did you last feel completely out of your depth?
- Which habit are you most proud of breaking?
- What's a compliment you've never been able to accept?
- When were you most wrong about a person?
- What's a goodbye you wish you'd handled differently?
- Which part of yourself took the longest to like?
- What did you quit that you wish you'd stuck with?
- What did failing teach you that winning never could?
- Which fear has held you back the most?
- What would you do differently if you could start your twenties again?
- What are you still learning to let go of?
Deep questions about the future
15- What do you hope never changes about you?
- Where do you want to wake up on your 70th birthday?
- What do you want to be remembered for?
- What would make the next five years a success, by your own measure?
- What's a dream you gave up on, and do you miss it?
- What scares you most about getting older, and what excites you?
- If you knew you couldn't fail, what would you start next month?
- What kind of old person do you want to be?
- What are you saving for that isn't money?
- What do you want to have stopped worrying about by 50?
- Who do you hope is still in your life in twenty years?
- What do you want to pass on to the next generation?
- Is there a place you're meant to live that you haven't found yet?
- What would you regret never trying?
- What does a quiet, ordinary good day look like in your future?
Deep questions to ask a friend
15- Which friendship changed who you are?
- What do you need from a friend that you rarely ask for?
- When did a friend tell you something you didn't want to hear, and were they right?
- How do you know a friendship is worth fighting for?
- What's the loneliest you've ever felt, even with people around?
- Which friend from the past do you wish you'd kept?
- Is it easier for you to give help or to ask for it?
- What could I do to be a better friend to you?
- What do people misunderstand about how you show you care?
- Which of your friends makes you braver?
- What's a conversation we should have had years ago?
- How has our friendship changed you, if at all?
- When do you feel left out, even in a group you love?
- What do you wish more friends talked about?
- What's a promise you'd make to a friend for life?
Deep questions to ask your partner
15- When did you first feel at home with me?
- What's something you've never told me because the moment never came?
- What do you need from me on your worst days?
- Which part of our life together do you want to protect most?
- What's a dream of yours I don't know enough about?
- When do you feel most loved by me?
- What did you have to unlearn to be in this relationship?
- Is there a fear about us that you've never said out loud?
- What small thing do I do that means more to you than I realize?
- How could we argue better?
- Which version of our future excites you most?
- What do you think we're best at as a team?
- Is there something you've stopped asking me for?
- What have I taught you without knowing it?
- What do you hope we never stop doing?
Deep questions for late at night
15- What's a thought that keeps you up at night?
- Are we mostly the same people we were as kids?
- What would you say to your younger self in one sentence?
- Do you believe things happen for a reason?
- What do you think happens after we die?
- If you could get a true answer to one question about life, which question?
- What's the most beautiful thing you've ever seen?
- When did you feel truly free?
- What does happiness feel like in your body?
- Is it possible to really know another person?
- What do you only feel brave enough to say at night?
- If you could keep only one memory, which one would it be?
- What gives an ordinary day meaning for you?
- What makes a life well lived?
- What are you grateful for that you've never said thank you for?
How to have a deep conversation that doesn't feel forced
Deep questions need the right moment more than the right words. A question that lands beautifully on a late walk can feel like an interrogation across a busy table.
- Pick a calm settingA walk, a long drive, a kitchen after everyone else has left. Side by side often works better than face to face.
- Start lighter than you thinkOpen with Life or The future. Jumping straight to regrets makes people guard up.
- Answer firstGive your own honest answer before you ask theirs. It shows the question is safe.
- Listen longer than feels normalWhen someone stops talking, wait a few seconds. The real answer often comes after the pause.
- Let anyone passSome questions hit harder than expected. Draw a new card without making a thing of it.
| Start with | Go deeper with | |
|---|---|---|
| Your significant other | Love, The future | Your partner, Regrets and growth |
| Your boyfriend or girlfriend, early on | Life, Love | Values |
| A close friend | Life, Friendship | Late night |
| Someone you want to know better | Life, The future | Values |
| A group, late at night | The future, Values | Late night |
Some answers come easier without names
In Dronk's Pandora's Box, everyone writes an answer on the phone and the app reads them out without saying who wrote what. It's a gentle way to get honest answers in a group.
Get Dronk free on iPhone
What makes a deep question good
A deep question is not the same as a heavy one. The best ones are easy to start answering and hard to finish.
- Ask about moments, not labels. "When did you feel truly free?" gets a story. "Are you a free spirit?" gets a yes.
- Keep it about the person in front of you. Questions about their life beat questions about the state of the world.
- Don't use it to fix things. A deep talk is not the time to settle an argument. If something serious comes up, make a separate time for it.
- Mix in something light. If the mood gets heavy, a few random questions bring the laughter back.
Questions people ask
What are good deep questions to ask?
Good deep questions are open and about real moments, like "What's a lesson you had to learn twice?" or "Which friendship changed who you are?" This page has 120 of them in eight groups.
What are deep questions to ask your partner or significant other?
Try "When do you feel most loved by me?", "What do you need from me on your worst days?" or "Is there something you've stopped asking me for?" The Your partner group has 15 of them, and the Love group has 15 more.
What are deep questions to ask your boyfriend or girlfriend about love?
Start with "How do you know when you love someone?" or "Is love a feeling or a decision?" They work for a boyfriend or a girlfriend alike, and they're easier to answer than questions about your own relationship.
What are deep questions to ask a friend?
Ask about the friendship and what they need: "What do you need from a friend that you rarely ask for?" or "Which of your friends makes you braver?" For lighter questions, see our list of questions to ask your friends.
How do you get to know someone on a deeper level?
Ask about moments instead of facts, answer the questions yourself, and give people time to think. Start with the basics from our get to know you questions and move to the Life and The future groups here.
What if a deep question makes someone uncomfortable?
Let it go and draw a new card. Nobody owes an answer, and a skipped question often comes back on its own later.
Keep the night going
Updated