Couples & Dating · Warm

Relationship Deep Dive.60 deep questions for couples

Harder, more honest questions for couples who know the easy answers.

25–40 min 60 cards 1–2 people
What's inside
House rulesResentmentAttractionInsecurityBoredomPrioritiesSettling+53 more
Sample card

What scares you most about raising kids with me?

About the Relationship Deep Dive deck

This deck is for couples who already know the easy answers. It asks when you feel like you are at the bottom of your partner's list, what part of growing old together worries you, and which of your parents your partner reminds you of. Some cards are uncomfortable on purpose.

The first card sets the rule: pass on anything, no reason needed, and nothing said gets thrown back later. Keep to it. Play on an evening with nothing planned the next morning, and put the deck down if one question opens up something that needs more than a card game.

All 60 deep questions for couples

  1. Pass on any card you want, no reason needed. Nothing said here gets thrown back at you later.

  2. What did I do months ago that you're still a little angry about?

  3. How has your physical attraction to me changed since we first met?

  4. What is the one thing I do that makes you feel most insecure?

  5. Where in our relationship have you started to feel bored?

  6. When do you feel like you're at the bottom of my list?

  7. Where do you feel like you settled by choosing me?

  8. Name something you want in bed but have never asked me for.

  9. When do you catch yourself comparing me to someone you were with before?

  10. Which flaw of mine have you given up on and just learned to live with?

  11. If we were to break up tomorrow, what would likely be the reason?

  12. What have you given up or put off because of me?

  13. When was the last time I completely missed what you were trying to tell me?

  14. Where do you think my money habits are taking us?

  15. When is it hardest for you to trust me?

  16. Which argument do we keep having that we never actually finish?

  17. What did you stop asking me for because you got tired of asking?

  18. What are you not telling me right now because you think it would hurt me?

  19. What part of yourself do you hide from me because you expect me to judge it?

  20. Who were you before me that you miss being?

  21. What scares you most about raising kids with me?

  22. What do you keep quiet about just to avoid a fight with me?

  23. How does my family make things harder for us?

  24. Name an expectation of mine that you never actually agreed to.

  25. How do you think your past traumas affect how you treat me?

  26. Who in my life do you feel jealous of, even a little?

  27. Tell me about a time you felt lonely in the same room as me.

  28. Which of my apologies did you accept without actually forgiving me?

  29. Picture us at 80, still together. What part of that picture worries you?

  30. Which of my daily habits secretly drives you crazy?

  31. Do you feel I support your dreams, or do I just tolerate them?

  32. When does sex between us feel more like a habit than a choice?

  33. If you could change one aspect of my personality, what would it be?

  34. How long have you been carrying something by yourself that I never noticed?

  35. What compliment do you keep waiting for me to give you?

  36. Which line of yours do I keep crossing without you calling me on it?

  37. Describe the last time you felt a spark with someone who wasn't me.

  38. Where do you feel smarter than me, and where do you feel dumber?

  39. If an accident changed my face tomorrow, what are you afraid would happen to us?

  40. If everything fell apart tomorrow, how much of it would you expect to carry alone?

  41. Which of my friends do you tolerate rather than actually like?

  42. What do you handle for both of us that I have never once thanked you for?

  43. What have you done in this relationship that you still feel guilty about?

  44. How does my relationship with work and ambition wear on you?

  45. If the spark never comes back, what would keep you here?

  46. When did my anger last make you want to leave the room?

  47. What do you want to know about my exes, and what would you rather never hear?

  48. Tell me about a lie you've told me that you still think was kind.

  49. What do you do when you realize I'd rather look at my phone than at you?

  50. Do you think we are too dependent on each other? Or not enough?

  51. How do you feel about the person you've become with me?

  52. Which cruel thing have I said to you, joking or not, that you have never forgotten?

  53. What do you fantasize about that you've decided I could never give you?

  54. Who do you think holds more power in our relationship?

  55. If we had met ten years later, who would you have been by then?

  56. Who has been putting in more effort lately, and how long has it been that way?

  57. If I needed full-time care one day, what part of that scares you most?

  58. What ultimatum have you come close to giving me?

  59. What do I do in public that makes you want to disappear?

  60. Which of your parents do I remind you of, and when?

How to play Relationship Deep Dive

  1. Start the deck and read the first card out loud. Whoever wants to answer goes first, or go around the group.
  2. Swipe left or tap the arrow for the next card, and swipe right to go back. Skip any card that doesn't suit the moment. There are no points.
  3. Follow-up questions count. If an answer is interesting, stay on it before moving to the next card.

Going through every card takes about 25–40 min, but there's no need to finish in one sitting. The deck runs in your browser with nothing to install, and your place is saved on this device, so you can stop and pick it up later.

Further reading

Deep Conversations for Couples: How to Get Past the LogisticsLong relationships drift into talk about bills and schedules. What research on couples says about staying curious, five kinds of questions that help, and how to make it a habit.