Questions to Ask Your Girlfriend

Don’t worry, you’ve come to the right place…

If you have a girlfriend (as we presume you do if you made it to this list), you might be coming to the realization that the hard work of getting to know her didn’t stop after your first few dates. Open and meaningful communication is the bedrock of all strong relationships. It takes time and effort to come to know and understand someone, so we created a list of our favorite conversation starters to help you develop a deeper connection with your girlfriend.

From discussing future aspirations to exploring childhood memories, these questions are crafted to enhance intimacy and trust. No wrong answers, only opportunities to grow together. So settle in on the couch and dive in!

  1. What is the most trivial thing about which you have a strong opinion?
  2. What is your hottest take about the differences between men and women?
  3. If you woke up in the body of someone of the opposite gender, what would you be interested to find out or do?
  4. What is one thing you’re good at that people don’t expect?
  5. What was an early impression you had to me that is still true now that you know me better?
  6. In what ways are we becoming more like one another?
  7. What is a childhood habit or preference that you’ll never outgrow?
  8. Ideally, how would you spend your birthday?
  9. Describe your perfect day. Option 1) You are restrained to 24 hours, but you can transport yourself to anywhere in the world. Option 2) Your realistic perfect 24 hours.
  10. What is the luckiest thing that has happened to you? What is the unluckiest thing that has happened to you?
  11. What about being a man (or woman) do I least understand?
  12. How are you different than the person you were a year ago?
  13. What is a common misconception that people have about you?
  14. Other than me, who is your go to person when you are going through something?
  15. Who is your favorite friend?
  16. What is your most memorable experience from high school?
  17. Which of my friends do you feel like you’re still trying to figure out?
  18. Which one of us is more into gift giving / receiving?
  19. What is your favorite free activity that we do together?
  20. What do you think about public marriage proposals?
  21. If we had met five (or ten) years earlier, do you think we still would have liked each other?
  22. What outfit do you like the most on me?
  23. Do you remember what I wore on our first date?
  24. How aligned do you think we are politically?
  25. What about our relationship works so well for you?
  26. What percentage of the time have you kissed on the first date?
  27. What is your love language? Do you think about love languages when you are in a relationship or are they not something you place a lot of value on?
  28. If you had to pick one friend to make all your decisions for you, who would it be?
  29. Have you ever been told that you have a doppelgänger? If so, who is it?
  30. What is the biggest difference between what girls go through while dating and what men go through?
  31. Do you consider yourself to be a generally happy person?
  32. What is the biggest difference between us?
  33. Do you think a relationship can come back from cheating?
  34. What’s your favorite quality about yourself?
  35. Who are you closest to in your family?
  36. What is your favorite physical attribute of mine?
  37. What is your favorite personality trait of mine?
  38. What do you think your best friend thinks of me?
  39. What would your genuine reaction be if I got your name tattooed on me today without telling you?
  40. Which of us do you think is better with money?
  41. Which of us do you think is better equipped to raise kids today?
  42. What do you think our dynamic as parents would be like?
  43. Who is your hall pass?
  44. Can you remember a time you felt embarrassed by something you did in front of me?
  45. Have we farted in front of each other? Is this the first time we’re acknowledging this with one another?
  46. Do you get the ick? If so, what gives you the ick?
  47. What are your relationship dealbreakers?
  48. What is your most memorable experience from college?
  49. What do you think your best attribute as a boyfriend is?
  50. How do you think our physical relationship has changed over time?
  51. How would you describe to someone where we are in our relationship in only one sentence?
  52. Which one of us is more into physical touch?
  53. Which one of us is more into quality time?
  54. Which one of us is more into words of affirmation?
  55. Which one of us is more into giving / receiving acts of service?
  56. Have you ever had a New Year’s kiss?
  57. Which couple in our lives do we have the most similar relationship dynamic to?
  58. When were you first interested in me?
  59. What about dating norms do you think is outdated?
  60. How do you think about traditional gender roles?
  61. Do you have any premonitions about anything about our future?
  62. What was your favorite of the dates we’ve been on?
  63. What is something that you remember from our first date?
  64. What is something you remember from the first time we kissed?
  65. What one interest do you wish I shared with you more fully?
  66. Do you have a sex fantasy that we’ve never talked about?
  67. How do you think our friends think about us with respect to PDA?
  68. Which of us is more affectionate generally?
  69. Which of us is more emotional generally?
  70. Do you have any core beliefs about marriage?
  71. What qualities do you think I have that you envisioned in a future spouse?
  72. Why did your last relationship end?
  73. Have you ever been in a situationship?
  74. Do you think you work harder or less hard than your close friends?
  75. Which of us is more athletic?
  76. If we had a kid together, what attributes would you hope they would get from each of us?
  77. Was there a time in your life where you might have thought that I wasn’t your type?
  78. Which of us is more extroverted?
  79. How often do you think about the future?
  80. What stresses you out most about the next five years of your life?
  81. Have you ever been jealous before in our relationship?
  82. What do you think my best color is?
  83. How do I generally answer the phone?
  84. How good is your impression of me?
  85. Do you think we have a song?
  86. What was our hardest conversation that we’ve had to date?
  87. Tell me about a time that something I did stressed you out.
  88. When stalking a potential love interest, what is your methodology?