There are lots of different questions that you can ask your boyfriend to get to know him better, and you must know what some of them are. These questions can help you to become closer to your boyfriend in an authentic way. Communication is essential in any relationship, and asking each other specific personal questions can be great for the relationship. The more of these questions you ask each other, the closer you will ultimately be.

50 Questions to Ask Your Boyfriend:

  1. What quality do you most hope that your future child has?
  2. What accomplishment are you most proud of in your life and why?
  3. What is your favorite place that you have ever travelled to? Where haven’t you gone that you want to visit?
  4. What things about our relationship make you the most happy when you think about them?
  5. How long did you think our relationship would last when we first started dating?
  6. If you had to describe our love/relationship in one word, what would it be?
  7. What is your biggest fear with regards to this relationship and why?
  8. What is one difference between us that you really like?
  9. What is one similarity between us that you love?
  10. If a situation arose where I had to move far away, what do you think you would do?
  11. What is one of your favorite memories involving both of us?
  12. Tell me something that you would like to do together as a couple that we’ve never done before.
  13. What is your absolute favorite memory from childhood?
  14. What makes you feel the most safe and secure?
  15. What do you think is one of the biggest strengths of our relationship? What is the biggest weakness?
  16. What is one secret that you have never told me before?
  17. Do you want to have children at any point? If so, how many would you like?
  18. What is your favorite physical quality about me?
  19. How do you feel like you have changed as a person over the years?
  20. What is something you do when you just want to feel good and relieve stress?
  21. Is there a certain place you like to go when you feel like you need to get away from it all for a little while?
  22. What is one thing that you hope happens in the future of our relationship?
  23. What is your dream job and what are your ambitions for the future?
  24. Do you consider yourself more of a religious or spiritual person, or both?
  25. If you were able to live anywhere in the world, which place would you choose to call home?
  26. What is something that always cheers you up no matter how bad of a mood you are in?
  27. What do you consider the bravest thing you have ever done in your life so far?
  28. What is one of the biggest challenges that you have had to overcome in life to get to where you are now?
  29. How do you imagine your perfect girl? How does she look and what is her personality like?
  30. What is one personality trait or characteristic in a girl that must be present for you to date her?
  31. Which of your family members do you feel closest to and why?
  32. What is the very first thing that you do when you wake up in the morning?
  33. Which characteristics do you possess that you are most proud of? Which do you think need some improving?
  34. What is your favorite way to show someone you love and care about them?
  35. What do you do to calm down when you feel yourself starting to get angry and/or stressed?
  36. What is your idea of being romantic?
  37. How do you feel about the people that you have been in a relationship with in the past? Do you still keep in touch with any of them?
  38. Where exactly do you see yourself in five years? How about in ten years?
  39. What would you say is one of your biggest insecurities?
  40. If you were trapped on a desert island, what three things would you bring with you?
  41. What is one song that always gives you chills when you listen to it?
  42. What are three things that you think are really important in any relationship?
  43. Do you consider yourself good with money?
  44. How important are friends and family to you?
  45. What is something you have done or not done that you are truly ashamed of?
  46. Do you think that there are times when lying is acceptable?
  47. How important is having sex to you in a relationship?
  48. What is something that you want to change about yourself?
  49. What is one thing that you wouldn’t want any of your family members to know?
  50. If you could change one thing about how you were raised, what would it be?

Personal Questions To Ask Boyfriend: FAQ

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What’s The Reason To Ask Deep Personal Questions?

There are tons of different questions that you can ask your boyfriend to get to know him better, but these are some of the very best. These questions should help you to gain a better insight into the person you are with, thereby bringing you closer as a couple. Most people don’t actually take the time to ask each other these questions, so it is definitely something that you will want to consider doing.

The fact is that even people who have been in a relationship for years can still find out new things about their partner they didn’t know. If you want to get to know your boyfriend better, you will undoubtedly find that these questions will do the trick. This is a fun and effective way to learn more about each other, which can be an excellent idea if you have just recently started dating him. In the end you will be glad you decided to do this.


Anna Perkins is a relationship writer who offers her own forthright opinion over the worlds of dating, romance, relationships , marriage and friendships. She loves cats, traveling, spending time with her son and husband.

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