DATING ADVICE

75 Deep Questions to Ask Your Girlfriend

Small talk builds comfort. Deep questions build connection.

Couples who ask each other real questions stay curious about each other for years. These 75 questions go past "how was your day" into the territory where intimacy actually lives: dreams, fears, childhood, values, the future. Use them on late-night calls, long drives, or quiet evenings.

About her dreams

1. What did you want to be when you were little?
2. If money didn't matter, how would you spend your days?
3. What is one dream you have never told anyone?
4. Where do you see yourself in five years?
5. What would you do if you knew you couldn't fail?
6. Is there a skill you have always wanted to learn?
7. What does your perfect day look like?
8. If you could live anywhere in the world, where?
9. What is on your bucket list?
10. What legacy do you want to leave?

About her past

11. What is your happiest childhood memory?
12. What was your family like growing up?
13. Who shaped you the most as a person?
14. What is something you believed as a kid that turned out wrong?
15. What was your favorite age so far, and why?
16. Is there a moment that changed how you see the world?
17. What did teenage-you get right about life?
18. What is a tradition from your family you want to keep?
19. What is the bravest thing you have ever done?
20. What would you tell your 16-year-old self?

About love and relationships

21. What does love feel like to you?
22. How do you know when you trust someone?
23. What is your love language?
24. What is something small a partner can do that means everything?
25. Have you ever had your heart broken? What did it teach you?
26. What do you need most when you are upset?
27. What is a deal-breaker for you?
28. Do you believe people can change for love?
29. What is the most romantic thing anyone has done for you?
30. What makes you feel most loved?

About fears and vulnerabilities

31. What are you most afraid of?
32. What keeps you up at night?
33. Is there something you pretend doesn't bother you but does?
34. What is your biggest insecurity?
35. Have you ever felt truly alone?
36. What is a failure that still stings?
37. What do you worry people think of you?
38. Is there something you have never forgiven yourself for?
39. What would you do if you weren't afraid?
40. Who do you call when everything falls apart?

About values and beliefs

41. What matters more: success or happiness?
42. What is a value you will never compromise?
43. Do you think everything happens for a reason?
44. What does a meaningful life look like to you?
45. Is it more important to be kind or honest?
46. What is something popular you secretly disagree with?
47. How do you define loyalty?
48. What would you stand up for even if it cost you?
49. Do you believe in second chances?
50. What is the best advice you have ever received?

Fun deep ones

51. If you could have dinner with anyone, dead or alive, who?
52. What superpower would you pick and why?
53. If your life were a movie, what genre would it be?
54. What is a weird hill you will die on?
55. If you could time-travel, past or future?
56. What song describes your life right now?
57. Desert island: three things?
58. What is a conspiracy theory you low-key believe?
59. If animals could talk, which would be the rudest?
60. What would your autobiography be titled?

About the future together

61. Where do you want to travel together first?
62. What does our life look like in ten years?
63. What is something you want us to try together?
64. How do you imagine our first home?
65. What traditions should we start?
66. What do you want to teach our kids someday?
67. What is a dream we could chase together?
68. How will we handle our first big fight?
69. What does growing old together look like to you?
70. What is one thing you want us to never lose?

Just between you two

71. When did you first realize you liked me?
72. What is your favorite memory of us?
73. What is something I do that you secretly love?
74. What do you want more of in our relationship?
75. What are you most grateful for about us?

How to ask them right

Deep questions need the right moment — not rapid-fire over lunch. Pick one, ask it slowly, and then actually listen. Share your own answer too; vulnerability is reciprocal. One real conversation beats a hundred shallow ones.

Go deeper tonight

Nia loves conversations that go beneath the surface — dreams, fears, the big questions. Ask her a few of these and discover how deep a chat can go.