Are you looking for ways to deepen your relationship with your significant other? If that’s the case, we've compiled the ultimate list of questions to ask that might just get the ball rolling.

Ranging from casual preferences to sex – these questions will help you and your partner navigate important conversations about what matters to each of you.

To make the most out of this open communication, you must first create a space where you can speak freely and without any distractions. So put your phone on do not disturb, turn off any background noise, and use this random number generator to get started.

  1. If someone asked, “What’s the best thing about your partner,” what would you say?
  2. What’s one thing I do that makes you feel cared for?
  3. What’s a small thing I can do that would make you feel more cared for?
  4. What was your first impression of me?
  5. Have you ever been in love?
  6. Would you change anything about our first encounter?
  7. What was the first thing you noticed about me?
  8. What do you feel most grateful for in your life?
  9. What is your favorite memory?
  10. Is there something that you want that you haven't asked me for?
  11. What makes you feel most loved?
  12. What insecurity holds you back the most?
  13. Do I remind you of anyone?
  14. What was your first kiss like?
  15. What is a piece of wisdom you’ve learned from me?
  16. What’s your love language?
  17. What is my love language?
  18. What is the first image that comes to mind when you think of me?
  19. What’s one thing in your love life and relationships that used to bother you but you’ve since overcome?
  20. What’s something you wish I understood more?
  21. What’s something you wish I empathized more with?
  22. Is there something you wish we could do together that we don’t do now?
  23. What is something about me that you find difficult to understand?
  24. Is there something that you’ve dreamed of doing for a long time? Why haven’t you done it?
  25. What’s one thing about yourself that you would change?
  26. What are three qualities you admire about me?
  27. What are three qualities you admire about yourself?
  28. What do you like best about our relationship?
  29. What is the hardest part of our relationship for you now?
  30. What compliment do you like hearing most?
  31. What are some ways we can evolve to make our relationship better?
  32. If you were convinced that I was making a bad decision, what would you do about it?
  33. Which song best describes our relationship?
  34. What’s are your greatest fears tied to our relationship?
  35. What about our relationship makes you feel happy?
  36. Over the last five years, how do you think you’ve changed?
  37. What’s the craziest thing you’d be willing to do for me?
  38. What is something you’re too afraid to ask me about?
  39. What question are you hoping I ask you?
  40. What question are you hoping I never ask you?
  41. What do you think is the most important thing for a successful relationship?
  42. What’s a relationship deal-breaker for you?
  43. What do you value most in friendship?
  44. If all your friends were asked to describe you, which friend’s description would be the most accurate and why?
  45. What values do you hope to keep five years from now?
  46. Where do you see yourself in five years?
  47. When you think about the future, where do you see yourself? Where do you see us?
  48. Have you ever dreamed about me?
  49. Do you have any kinks?
  50. What’s your wildest sexual fantasy that you’d want to try?
  51. What’s your wildest sex story?
  52. What did you think I would be like in bed? What am I actually like?
  53. What is your favorite part of foreplay?
  54. What were your first words as a child?
  55. What did you want to be when you grew up?
  56. Who had the greatest influence on your life?
  57. If you could change anything about the way you were raised, what would it be?
  58. How’s your relationship with your family now?
  59. What qualities do you like about each of your parents?
  60. What qualities do you not like about them?
  61. Do you want to have kids one day? If so, how many?
  62. What is your most treasured memory?
  63. What is your least favorite memory?
  64. When did you last sing to yourself? To someone else?
  65. What was one of the most embarrassing moments in your life?
  66. When was the last time you cried in front of another person?
  67. When was the last time you cried by yourself?
  68. What was a subject you excelled at in school?
  69. What was one of your favorite books as a child and why did you like it so much?
  70. What is one of the most adventurous things you have ever done?
  71. When was the first time you fell in love?
  72. Have you ever tried online dating?
  73. What is your funniest date story?
  74. What is your worst date story?
  75. What were you like in high school?
  76. What does your ideal day look like?
  77. If you could plan the perfect date with me, what would that include?
  78. What do you do when you can’t go to sleep?
  79. What is your greatest fear?
  80. What’s a hobby you enjoy I may not know about?
  81. If you could do anything for work and not worry about money, what would you do?
  82. If you’re having a bad day, what would you want me to do to make it better?
  83. If you could wake up tomorrow having gained any one quality or ability, what would it be?
  84. Who are your five dream dinner guests (from any point in history)?
  85. If you could witness any event in history, which one would you choose?
  86. Who would play you in a movie about your life?
  87. If you were to die this evening, what would you most regret not having told someone?
  88. If you could trade lives with someone, who would it be?
  89. What’s your favorite movie?
  90. What’s your favorite book?
  91. What’s your favorite type of food?
  92. What’s your favorite holiday?
  93. What’s your most treasured possession?
  94. If you had a crystal ball that could tell you anything about your life that you don’t already know, what would you ask it to tell you?
  95. Where is somewhere in the world you still want to visit?
  96. What would be your dream vacation? How would you spend that time?
  97. Do plants thrive or die in your care?
  98. What are five things that are on your personal bucket list?
  99. What are three things in your life you could not imagine doing without?
  100. What are five things that you are most thankful for right now?