Deep Questions for Couples

Deep questions help you get past everyday logistics and talk about what really matters: what you value, what you are afraid of, what you want your life to look like and what you need from each other. Asked at the right moment, one deep question can teach you more about your partner than a month of small talk.

These questions are sorted by depth. Start at level 2 to warm up and move to level 3 when you are both relaxed and have time. Take turns, listen without interrupting and ask a follow-up before you share your own answer. Play on one phone, or start a room to answer from two phones. Anything can be skipped.

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  1. 1

    If you could invite anyone in the world to dinner, who would it be?

  2. 2

    Would you like to be famous? In what way?

  3. 3

    Before making a phone call, do you ever rehearse what you'll say? Why?

  4. 4

    What would a "perfect" day look like for you?

  5. 5

    When did you last sing to yourself? And to someone else?

  6. 6

    If you could live to 90 and keep either the mind or the body of a 30-year-old for the last 60 years, which would you choose?

  7. 7

    Do you have a secret hunch about how you will die?

  8. 8

    Name three things you and I seem to have in common.

  9. 9

    What in your life do you feel most grateful for?

  10. 10

    If you could change anything about the way you were raised, what would it be?

  11. 11

    Take four minutes and tell me your life story in as much detail as you can.

  12. 12

    If you could wake up tomorrow with one new ability or quality, what would it be?

  13. 13

    If a crystal ball could tell you the truth about yourself, your life or the future, what would you want to know?

  14. 14

    Is there something you've dreamed of doing for a long time? Why haven't you done it?

  15. 15

    What is the greatest accomplishment of your life?

  16. 16

    What do you value most in a friendship?

  17. 17

    What is your most treasured memory?

  18. 18

    What is your most painful memory?

  19. 19

    If you knew you would die suddenly in one year, would you change anything about how you live now? Why?

  20. 20

    What does friendship mean to you?

  21. 21

    What roles do love and affection play in your life?

  22. 22

    Take turns sharing something you consider a positive trait of mine. Share five each.

  23. 23

    How close and warm is your family? Do you feel your childhood was happier than most people's?

  24. 24

    How do you feel about your relationship with your mother?

  25. 25

    Make three true "we" statements each, like "We are both in this room feeling…"

  26. 26

    Complete this sentence: "I wish I had someone with whom I could share…"

  27. 27

    If we were going to become close friends, what would be important for me to know?

  28. 28

    Tell me what you like about me — be very honest, and say things you might not say to someone you just met.

  29. 29

    Share an embarrassing moment from your life.

  30. 30

    When did you last cry in front of someone? By yourself?

  31. 31

    Tell me something you already like about me.

  32. 32

    What, if anything, is too serious to be joked about?

  33. 33

    If tonight were your last chance, what would you most regret not having told someone? Why haven't you told them yet?

  34. 34

    Your home catches fire. After saving your loved ones and pets, you have time to safely grab one item. What would it be and why?

  35. 35

    Whose death in your family would you find most disturbing? Why?

  36. 36

    Share a personal problem and ask how I might handle it. Then ask me to reflect back how you seem to be feeling about the problem you chose.

  37. 37

    When do you feel most connected to me?

  38. 38

    What's something you've never told me but want to?

  39. 39

    How has being with me changed you?

  40. 40

    What's a fear you carry that you rarely talk about?

What are deep questions to ask your partner?

Questions like "What do you need from me when you are stressed?" or "What does a good life look like to you in ten years?" They ask about values, fears and hopes, not just facts.

When is the best time to ask deep questions?

When you are both rested and have at least thirty minutes without distractions - a walk, a long dinner or a quiet evening at home. Avoid starting when either of you is tired or upset.

What if my partner does not want to answer?

Let them skip with no pressure. Some people need time to think; you can come back to the question another day.

Are deep questions good for a new relationship?

Some are. Stick to level 2 early on and save the level 3 questions for when you both feel more secure.