Even after nine years with my partner, I’m still finding out new information about them day after day — and it makes me love and respect them even more. 🫶

“Deepening our relationship requires real, concerted effort in order to learn about each other and to grow together.”

After all, deepening our relationship requires real, concerted effort in order to learn about each other and to grow together. The Gottman Institute, one of the leaders in couples counseling and marriage, found that “if you ask questions that require only a yes or no answer, you hinder conversations before they can even begin…with open-ended questions, the door for a deeper connection is unlocked.”

So, whether you’re in the early stages of your relationship or you’re decades in (#goals), here’s hoping that you’re able to pose one of these 99 open-ended questions below to learn something new about your partner. If you have other prompts you recommend, drop them in the comments!

PS: If you’re yearning for a longer one-on-one discussion, check out these 99 conversation topics. Or if you’re trying to do some introspection, consider these 99 reflective questions for your own personal growth.

1. What accomplishment are you proudest of in your life?

2. Describe your ideal lazy Sunday. (And should we have one next week?)

“What beliefs from your parents did you inherit that you want to keep?”

3. What beliefs from your parents did you inherit that you want to keep?

4. What about the ones you’re hoping to unlearn?

5. If you could eat just three meals for the rest of your life, what would you choose?

6. What’s the happiest memory you can think of from childhood?

7. Tell me about the teacher who taught you most in life, formal or otherwise.

“If you could do it all over again, would you still pick the same career?”

8. Which qualities do you appreciate most in me, and why?

9. If you could do it all over again, would you still pick the same career?

10. What bucket list adventures or travels are still on your list?

11. Or, which previous trips have left a lasting impression on you?

12. Do you ever wish you lived in a different place? Why or why not?

“What social issue do you care about the most?”

13. What are your favorite physical traits, and why?

14. What social issue do you care about the most?

15. What’s your attachment style?

16. How can I be a better partner to you? What do you need from me right now?

17. Where do you see yourself in the next five, 10, or 20 years? Describe your perfect life at 65.

18. Tell me about your pet peeves and frustrations—and where they came from.

19. What are your biggest creature comforts (i.e., a comfort movie, meal, playlist)?

“If you could pick three of your character traits to pass on, what would you choose?”

20. If you could pick three of your character traits to pass on, what would you choose?

21. Cat or dog person? Neither? Both? Rabbits?

22. What outfit or look makes you feel most confident?

23. If you could only hear five songs or bands forever, who would you listen to? Why?

24. What’s an embarrassing moment from your past that you can laugh about today?

“What would you do every day if money were no object?”

25. How do you feel you’ve professionally or personally grown over the years?

26. What would you do every day if money were no object? How would you choose to spend your time?

27. What’s your approach to personal finance? Are you a bigger saver or spender, and why?

28. Tell me about the most sentimental object you own (or remember having)—what did it mean to you?

29. What’s your approach to dividing up housework between partners? What are your preferred household chores?

30. What’s the best way for you to recharge or rest?

“Were you ever a ‘late bloomer’ in any aspect of your life?”

31. Were you ever a “late bloomer” in any aspect of your life (i.e., puberty, first loves, etc.)?

32. How will I know when you’re feeling stressed or overwhelmed? What can I do to support you when you are?

33. Tell me about the people you care about most deeply. (Or, tell me about your childhood best friend, grandparent, or other loved one.)

34. If you could manifest anything right now, what would that be?

“How do you address conflict or tension within a relationship?”

35. How do you address conflict or tension within a relationship?

36. What’s a skill you hope to hone this year? Or a new hobby you want to try?

37. Describe your ideal date night. (And we don’t mean April 25… IYKYK. 😆)

38. In retrospect, can you recognize a defining moment in your life where things would have gone differently otherwise?

39. How would you describe your dream living space?

40. Tell me your views on therapy.

41. Which book, movie, or other piece of media has stayed with you?

“Which holiday is your favorite (if any), and what traditions help you enjoy them?”

42. How do you know you’re in love?

43. Can you share more about any sexual desires or fantasies you’ve had lately, maybe any that you’d be open to trying?

44. What have your past relationships taught you?

45. Which holiday is your favorite (if any), and what traditions help you enjoy them?

46. What personal challenge or hardship has molded you the most?

“What have your past relationships taught you?”

47. How do you feel about concepts like fate, destiny, or karma? What about practices like astrology, tarot, or aura readings?

48. Do you have an ideal “timeline” of your life? What does it look like?

49. Are kids part of your (or our) future? If so, how would you like to parent them?

50. What do you think are the most important parts of being a good friend, partner, child?

51. What brings you childlike joy and wonder?

52. Yay or nay?: Celebrating anniversaries, talking about your sex life with close friends, doing monthly money check-ins, etc.

“Have you ever experienced grief?”

53. What’s something people wouldn’t know about you just from looking at you? Or what part of you feels most misunderstood?

54. Are you a morning person or a night owl…or something in between? What’s your chronotype?

55. Have you ever experienced grief?

56. Do you ever dream about starting your own business? What would it be?

“What scent do you find most comforting or nostalgic?”

57. If you won the lottery, how would you spend your winnings?

58. What scent do you find most comforting or nostalgic?

59. On a scale of 1 being messy to 10 being neat as a pin, how clean is your space?

60. Tell me what a healthy marriage or long-term partnership looks like for you.

61. What are you most afraid of? Or more intimately, what fears do you have about our relationship?

62. Name the top five people you’d invite to your dream dinner party, and why.

63. If you feel comfortable, share your worst dating experience.

“Who was your first crush, whether IRL or celebrity?”

64. Who was your first crush, whether IRL or celebrity?

65. Everyone has their strengths—what are you better at than most people?

66. What are you most grateful for?

67. How do you hope to be remembered one day?

68. Which family member or loved one do you feel closest to?

“What year of your life would you re-live, if you had the choice?”

69. What year of your life would you re-live, if you had the choice?

70. What decade of life are you most looking forward to?

71. Can you tell me about any regrets you currently have? (Or, something you thought you’d regret but actually don’t?)

72. As a kid, what did you want to be when you grew up? Do you think that’s still something you’d want to pursue in any way, even as a hobby?

73. What’s the best advice you’ve ever received? What about the best you’ve ever given?

74. Share the happiest moment you can think of from our relationship so far.

75. What boundaries are most important to you?

“What boundaries are most important to you?”

76. Who’s your role model? Who do you respect most?

77. What’s on your wishlist to buy right now?

78. When’s the last time you cried?

79. What goes through your mind when you’re falling asleep at night?

80. Tell me about a time you laughed so hard your stomach hurt.

“Do you believe in an afterlife?”

81. What foods do you find yourself craving the most?

82. Do you believe in an afterlife?

83. What shared goals do you want to work on together?

84. What’s something you believe is always worth spending money on?

85. At the end of your days, how would you define a “successful” life?

86. What were family dinners or gatherings like for you as a child? Do you hope to do the same with your own family?

87. What’s your “guilty” pleasure? (Side note: There are very few things worth feeling guilty about!)

88. What do you need from me right now?

“Can you name a couple whose relationship you admire?”

89. Can you name a couple whose relationship you admire?

90. Which birthday has been most memorable (so far)?

91. Tell me your non-negotiables for a happy, healthy, long-term partnership.

92. How do you handle change?

“If you outearn me or I outearn you, how would you want us to approach our finances?”

93. What are your pet peeves or concerns when it comes to living with someone else?

94. If you outearn me or I outearn you, how would you want us to approach our finances?

95. What’s your favorite form of exercise/movement, whether to do alone or together?

96. Which of my accomplishments are you most proud of?

97. Can we agree to do an act of kindness every single day? (It can be for ourselves, each other, or together for a stranger or loved one!)

“What is your favorite memory of us together?”

98. Tell me something I don’t already know about you.

99. What is your favorite memory of us together?

Henah Velez (she/her) is the Senior Editor at Money with Katie at Morning Brew, as well as a writer at The Good Trade. She holds a Master’s in Social Entrepreneurship and is a proud Rutgers grad. Originally from NJ, Henah’s now in the Bay Area where she loves shopping small, hanging with her pets, or traveling.