50 Intimate Questions to Ask Your Girlfriend or Boyfriend


Asking intimate questions may feel unnatural to you but it is one of the easiest ways to uncover your partner’s most secret desires and dreams. If you’ve been involved in a serious relationship, you know there were times when you would have loved to know what your significant other was thinking. This is especially true of boyfriends, who often struggle to reveal their girlfriend’s most inner secrets.

Some may say that men are inept at noticing the small details that reveal so much. Others hint to the idea that men are poor listeners. These generalizations are applicable to many men, but to unlock the mysteries of a woman’s mind may be as easy as asking a few well-timed questions.

Men struggle to find the right words or questions that peel back the layers. They prefer uncomplicated situations, and so, when it comes time to probe into sensitive matters, they often fumble to come up with that crucial question that could reveal the intimate knowledge they so eagerly seek. Here is a list of questions that you may consider asking your girlfriend to gain a better perspective on her thoughts and feelings.

  1. How long do you see our relationship lasting?
  2. What was it about me that first caught your attention?
  3. Was there ever a time early on in our relationship when you doubted it would work, and if so, what initiated that thought?
  4. If there were one thing you could change about me, what would it be?
  5. What would you say is my most redeeming quality?
  6. Do I give you the emotional support you need?
  7. What are some things that I need to work on that could enhance our relationship?
  8. Do you ever stop and wonder if you’re being a great girlfriend?
  9. What is the one thing you think you need to improve on as a person in order for our relationship to take the next step?
  10. What is the one thing you think I need to improve on as a person in order for our relationship to take the next step?
  11. Is there anything about our relationship that when you think about it makes you unhappy?
  12. Have I ever hurt you in any way that you’ve never told me?
  13. How upset would you be if for some reason we were forced to end our relationship right now?
  14. If we had only a week left to be together, what are some things you’d want to experience with me in that week?
  15. Did you ever worry that your family wouldn’t like me? If so, why?
  16. Do you ever wonder about my inner most thoughts the same way I do about yours?
  17. Are there issues you’ve wanted to talk to me about but were too scared to bring them up, and if so, what are those issues?
  18. Have you ever considered how different your life would be if we didn’t meet? If so, do you usually focus on the negatives or positives?
  19. Where do you see yourself in five years?
  20. Which aspirations and goals of yours do you worry you’ll never achieve?
  21. If you were free from all of life’s constraints, what would you want to do every day?
  22. Do you have any regrets, and if so, what are they?
  23. If you could go back in time and redo one moment in your life, what moment would it be?
  24. Do you see yourself getting married? Do you want to have children, and if so, how many would you like to have?
  25. Where do you see us in five years?
  26. What values in life are most important to you?
  27. What could I do to prove that I love you?
  28. What would you do to show me how much you love me?
  29. Would you be hurt if I said I still had feelings for someone else?
  30. Do you still have feelings for someone in your past?
  31. Would you be able to forgive me if I was intimate with someone else while we were dating?
  32. Have you ever cheated on a boyfriend?
  33. Would it change how you think about me if I told you that I was unfaithful to one of my former girlfriends?
  34. Do you feel comfortable enough to tell me anything?
  35. Would you be upset if you knew that I had secrets that I withheld from you?
  36. How important is a physical attraction to you?
  37. How important is sex to you?
  38. Is there something I could do in bed that would make our sex life more enjoyable for you?
  39. Ideally, how often would you like to have sex?
  40. Would you ever tell me if you had a sex dream about an ex-boyfriend?
  41. Would it bother you if I watched porn? Would it bother you if I masturbated to other people besides you? Would it bother you if I masturbated at all?
  42. Do you have any fantasies you’d like to fulfill, and if so, what are they?
  43. Specifically, what turns you on?
  44. In which of your past relationships were you the happiest? Why did it end?
  45. Have you ever loved anyone more than you love me? If yes, could you ever see that changing?
  46. When you think about me, what’s the first thing that pops into your head?
  47. Did your parents have a good marriage? Was there anything about their marriage that you hope you don’t repeat?
  48. If I were to suffer a permanent deformity from an accident, would you still stay with me?
  49. If you were to suffer a permanent deformity from an accident, would you expect me to stay with you?
  50. What can I do better during our disagreements that will help to resolve the issue quicker?

Did YOU know?

1) Only 9 percent of women and 2 percent of men found a relationship at a bar or club

2) 38% of singles are using online dating

3) One in six marriages now begin online

It’s understandable to feel a tinge of awkwardness when discussing some of the issues that these questions attempt to shed light upon, but if you ask most people, the number one key to a healthy relationship is good communication. Remember though, it’s probable that not every one of her answers will bring a smile to your face. In fact, you should probably question the validity of her answers if they are exactly what you had hoped to hear. But ask the questions anyway, and have faith that openly discussing those intimate matters will go a long way in strengthening your relationship.