120 Deep Questions to Ask Your Partner, Friends & Yourself

How to ask deep questions well

Deep questions work best when they feel like an invitation, not a test.

• Pick the moment. A walk, a long dinner, a drive or a quiet evening at home all work. A loud bar or a rushed morning does not.
• Answer first, or answer too. Going first shows how much detail you are comfortable sharing. A conversation where only one person talks feels like an interview.
• Ask a follow-up. “What was that like?” or “What happened next?” is often better than the next question on the list. Stay with a good answer.
• Allow a pass. Nobody has to answer every question. Skipping one is fine, and knowing that makes people more honest on the next.

Easy deep questions to ease in

Start here if the mood is still light. These are meaningful but low pressure.

1. What is a small thing that made you happy this week?
2. Which place feels most like home to you, and why?
3. What is a smell or a song that instantly takes you back somewhere?
4. What is the best piece of advice you have ever been given?
5. What do you do when you need to recharge?
6. Who is someone you could talk to for hours?
7. What is a tradition you hope to keep for life?
8. What is something you are looking forward to right now?
9. What is a skill you wish you had picked up years ago?
10. What is the kindest thing a stranger has done for you?
11. What does a perfect ordinary day look like for you?
12. What is something you used to dislike but now love?

Deep questions to ask yourself

These are good for a journal, a long walk or a quiet Sunday.

1. What am I pretending not to know right now?
2. What would I do differently this year if nobody were watching?
3. Which of my habits is quietly helping me, and which is quietly costing me?
4. When do I feel most like myself?
5. What am I holding on to that I should probably let go of?
6. Whose approval am I still chasing?
7. What is a fear that has shrunk since I faced it?
8. What do I say yes to out of guilt rather than want?
9. What would I tell my younger self about the thing I am worried about now?
10. Which part of my day do I wish I could stretch, and which do I wish I could skip?
11. What does enough look like for me?
12. What is something I have never told anyone because it felt too small or too silly?
13. When was the last time I surprised myself?
14. Which relationship in my life deserves more of my attention?
15. If I stopped worrying about how it looks, what would I change first?

Deep questions to ask your partner

Save these for a calm evening. Take turns, and listen more than you advise.

1. When did you first feel that this relationship was serious?
2. What is something I do that makes you feel most understood?
3. What did your family teach you about love, for better or worse?
4. When do you feel closest to me?
5. What is something you wish we talked about more often?
6. How do you like to be comforted when you are having a hard day?
7. What is a memory of us that you replay when you want to smile?
8. What is one thing you are afraid to ask me for?
9. What do you think we are really good at as a team?
10. Which of your dreams do you worry gets less attention than it deserves?
11. What does a good argument look like to you, and what does a bad one look like?
12. What is something you admire about me that I might not know?
13. How have you changed since we met?
14. What does feeling supported look like in practice?
15. What is something you want us to try in the next year?
16. Which of our differences have turned out to be a strength?
17. When have you felt most proud of us?
18. What do you need more of from me right now, and what do you need less of?
19. What is a rule or habit from your childhood you want us to keep or drop?
20. If we had a free month with no obligations, how would you want to spend it?

Deep questions to ask friends

Best with two or three people. Try them on a road trip, at a long dinner or by a fire.

1. What is a decision that changed the direction of your life?
2. Who taught you the most about being a good friend?
3. What is something you are proud of that you rarely get to talk about?
4. When did you last feel like you were exactly where you were supposed to be?
5. What is a belief you held strongly at twenty that you no longer hold?
6. What is the best thing a friend has ever done for you?
7. What do you wish more people knew about you?
8. Which friendship in your life has taught you the most?
9. What is something you are still figuring out?
10. When do you feel like you have to perform for other people?
11. What is the most generous thing you have ever done?
12. What part of your life would surprise your friends from ten years ago?
13. What do you need from a friend when you are going through something tough?
14. Which version of yourself do you miss?
15. What is a risk you took that paid off, and one that did not?
16. How do you want to be remembered by the people in this room?
17. What is a conversation you wish you had had sooner?
18. What is something you admire about each of us here?

Deep questions to ask someone you are getting to know

These stay warm and a little curious without getting too personal too fast. Move from the first few to the last few as the conversation settles.

1. What is something you could talk about for an hour without noticing the time?
2. What did you want to be when you were ten, and what do you think of that now?
3. Who has had the biggest influence on how you see the world?
4. What kind of environment helps you do your best thinking?
5. What is something you have changed your mind about in the last few years?
6. What makes a day feel well spent to you?
7. What is a place you have been that you would send everyone to?
8. What does a good friendship look like to you?
9. What is something you are curious about right now?
10. What is a small moment from your life that you think about more than you would expect?
11. What do you value most in the people around you?
12. What is something you are working on getting better at?
13. When do you feel most energized?
14. What is the best thing about where you grew up?
15. What question do you wish people asked you more often?

Philosophical “what if” questions

Good for long dinners and slow evenings. There are no right answers, only interesting ones.

1. If you could know the exact date of one future event, would you want to?
2. If you could replay one day of your life exactly, which day would you pick?
3. Would you rather be certain about your choices or free to change them?
4. If everyone could read your thoughts for one hour, what would worry you most?
5. If you could swap lives with someone for a week, who would it be?
6. Would you want to live forever if the people you love did not?
7. If you had a free year with no money worries, what would you do with it?
8. Is it better to be admired or to be understood?
9. If you could erase one common habit from the whole world, which would it be?
10. If you could ask your future self one question, what would it be?
11. Does a person change at their core, or do they just get better at hiding or showing who they are?
12. If you had to teach one lesson to everyone alive, what would it be?
13. Would you rather have a life with few big adventures or many small comforts?
14. If luck is part of success, how should we think about those who have a lot of it?
15. What would you do if you knew you could not fail?

Deep questions about the past

Ask for a specific memory. It makes the answers vivid and easy to give.

1. What is your earliest happy memory?
2. Which teacher, coach or neighbor stuck with you, and why?
3. What was the hardest thing about being a teenager for you?
4. What is a moment from your past that you are surprisingly proud of?
5. When did you first realize your parents were just people?
6. What is a mistake that taught you something you still use?
7. Which year of your life would you most like to revisit for a day?
8. What was the best phase of your life so far?
9. Who did you lose touch with that you would like to talk to again?
10. What is something you did as a kid that you wish you could still do?
11. What is a risk you took that you would take again?
12. What did you believe about adulthood that turned out to be wrong?

Deep questions about the future

Look ahead together. These work well at the start of a new year or a new chapter.

1. What does a good life look like to you in ten years?
2. What is one thing you hope is true of you by this time next year?
3. Where would you live if you could pick anywhere?
4. What do you want to be known for?
5. What is something you want to learn before you turn a decade older?
6. Which habit would you like to build, and what is stopping you?
7. What would make you feel at peace with how you spend your time?
8. Who do you want to spend more time with in the years ahead?
9. What is a trip you want to take at least once in your life?
10. What is a goal you have kept quiet because saying it out loud feels risky?
11. What would you like to be doing on an ordinary Tuesday five years from now?
12. What do you hope you will never lose?
13. What is one thing you want to let go of before the next year starts?

Turn deep questions into a game

If asking out loud feels stiff, add a few simple rules.

• The bowl. Write the questions on slips of paper, fold them and draw one at a time. Everyone answers the same question, or only the person who drew it.
• Take turns. Go around the table. Each person picks a section, draws a question and answers. The person to their left asks one follow-up.
• The pass rule. Everyone gets two passes for the night. Using a pass means you draw a new question instead.
• Easy to hard. Start with the “ease in” section, move through the middle and end on the future questions so the night closes on a warm note.

If you want something on your phone instead of paper, Duoo is an iPhone app with party games for 2 to 8 players on one phone, and it works offline. It has question games like Would You Rather, though it is not a dedicated deep questions app, so a printed list or a bowl of paper slips works just as well. For more lists, see questions to ask your partner, questions to ask friends, questions to ask to get to know someone and hot seat questions.