Skip to Content

90 Enrichingly Deep Questions to Ask Your Boyfriend

90 Enrichingly Deep Questions to Ask Your Boyfriend

Sharing is caring!

Deep questions to ask your boyfriend…

Have you ever wondered what people mean when they say to ask the right questions in a relationship?

If you have, this was written with you in mind.

Think about this; we all know how important communication is in any relationship.

Relationship experts and counsellors lay emphasis on effective communication and how it strengthens our relationships.

Despite that, a lot of us are still lacking when it comes to communicating with our partners.

This is not to say that we don’t talk.

But when we hear advice on communication, what really comes to our mind is settling misunderstandings and quarrels.

However, communicating with your partner goes deeper than that; it is about knowing them and how they think; knowing their likes and dislikes; knowing what makes them tick.

It is even much more important to know the deep questions to ask your boyfriend especially if you are interested in getting married to him.

How do you know you should be considering marrying him? It is when you actually know him.

And how do you know him? By asking the right questions.

So, what are the deep questions to ask your boyfriend?

90 Deep Questions To Ask Your Boyfriend

1. When was your last relationship and why did it end?

While you might not need all the details, you should know what happened. What he picked from that relationship and how it might affect yours.

2. Are you religious?

Whether you are religious or not, this question is important to know if you and your partner are on the same page about religion.

3. What does happiness/success mean to you?

You want to know this to know whether your ideas of happiness and success tallies or not.

This is because what you both define as success or happiness will determine your goal in life and how you reach for it.

4. Do you want children?

I think many people take it for granted that children are a given when people get married but we are seeing increasingly that some people don’t want children.

So, it is necessary to ask whether you want them or not.

5. Do you have a best friend? Who?

You most likely already know this. But if you don’t, ask.

You want to know the people he considers his confidants; they will most likely be a reflection of him.

6. What is your love language?

If you are yet to read The 5 Love Languages by Gary Chapman, you should.

It is essential to know yours and that of your partner.

7. What is your opinion on cheating in a relationship?

While women do cheat as well, we know that some men think it is their birthright to cheat.

So, you want to know where your partner’s head is at concerning the topic.

8. What are your deal breakers?

What can he not take in the relationship? What does he see as an absolute no-no? You need to know.

9. Have you ever struggled with an addiction?

This will help you understand him better and maybe certain decisions he takes.

10. How do you resolve conflict?

You want to be sure your boyfriend is not one who results in silent treatment or emotional abuse or violence when he is angry.

You need to know whether he acts maturely during conflicts.

Serious Questions to Ask Your Boyfriend

The aim of asking your boyfriend these serious questions is to know him beyond things like his favourite food and colour.

Although those are also important, you want to know how he sees life or will address life issues.

11. Where do you see yourself in five years?

12. what is the last accomplishment you felt proud of?

13. What is your happiest memory?

14. What was your childhood like?

15. What are your financial priorities?

16. What are your plans for retirement?

17. How do you want to be remembered?

18. If you could fix one problem, what would it be?

19. If a million dollars drops on your laps, how would you spend it?

20. What is that one thing you can never sacrifice for this relationship?

Intimate Questions to Ask Your Boyfriend

This set of questions will give you an insight into the kind of person he is and some of the reasons why he is the way he is, so you can understand him better.

21. Have you ever been in jail?

22. Do you have a child or have you ever gotten anyone pregnant?

23. What is your biggest regret in life?

24. If you could go back to the past, what is that one thing you would change?

25. What do you like and hate most about yourself?

26. When was the last time you cried and why?

27. What makes you vulnerable?

28. What is your biggest fear in life?

29. What was the most difficult thing you’ve had to deal with?

30. Have you ever cheated on anyone or being cheated on?

Romantic Questions to Ask Your Boyfriend

Would you even say you are in a romantic relationship if both of you cannot ask each other certain romantic questions?

Having romantic conversations is probably one way to separate a platonic relationship from a romantic one.

31. Who was your first love?

32. When was your first kiss?

33. What is your favourite way to give and receive affection?

34. What is the first thing you notice about a woman?

35. What drew you to me?

36. What part of my body is your favourite?

37. What is your idea of an ideal date?

38 What is your idea of the best romantic gift?

39. Whose relationship do you admire the most among your friends and family?

40. What is your favourite thing about our relationship?

Questions to Ask Your Boyfriend to See If He Knows You

You don’t just want to know him; you want to be sure he knows you too. These questions will help you determine that.

41. What makes me happy?

42. What is my biggest pet peeve?

43. What do I consider my biggest accomplishment?

44. What is my deal-breaker?

45. What are my future goals?

46. How do I act when I’m angry?

47. What are some of my insecurities?

48. Would you describe me as an introvert or an extrovert?

49. What is my love language?

50. What is my favourite thing about you?

Deep Questions to Ask Your Boyfriend About His Past

The reason history is said to be important is that you cannot properly understand the present without the past.

51. What was your best childhood memory?

52. What was your worst childhood memory?

53. What was your first sexual experience?

54. What is the riskiest decision you’ve ever taken?

55. What is the most challenging setback you’ve ever experienced?

56. When was your best and your worst past relationship?

57. What are some of life’s lessons you had to learn the hard way?

58. What is that one experience you had that made you the way you are now?

59. When last were you vulnerable?

60. What dreams did you have as a child? Have they changed or you are still pursuing them?

Fun Questions to Ask Your Boyfriend

Your relationship will be very boring if all you engage in is serious discussions. You should also not miss out on having plain fun.

61. Who is your celebrity crush?

62. If you could pick a dinner date, who would you pick and why?

63. What is your guilty pleasure?

64. Would you want to be a woman for a day if you could? What would you do?

65. Which movie character do you relate to the most?

66. If you could have a superpower, which would you want to have?

67. Tell me something embarrassing that has ever happened to you.

68. What are some of your fantasies?

69. What actor would you choose if there were to be a movie made about you?

70. What would you want to know if you could see the future?

Long Distance Relationship Questions for Him

Long distance relationship can be very stressful. So, you need to have conversations around your situation to make it easier for both of you. These questions will help as conversation starters.

71. What would you want me to do to make this easier for you?

72. How would you describe our emotional intimacy at the moment?

73. What your fondest memory of us when we were together?

74. What are you looking forward to doing together when we meet?

75. What are some of your challenges with the distance?

76. How long do you think you can cope with the distance?

77. What would be your ideal date when we meet?

78. What do you like and hate most about our relationship?

79. How best do you think we can handle our conflicts considering the distance?

80. Do you think we need to change anything about our communication?

Questions to Ask Your Boyfriend To See If He Likes You

These questions will give you an insight on what he thinks about you and the relationship.

81. What was your first impression of me when we met?

82. What does love mean to you?

83. When did you fall in love with me?

84. What do you like about me?

85. What don’t you like about me?

86. If you could change one thing about our relationship, what would it be?

87. What is your fondest memory about us?

88. If you were to dedicate a song to me, what song would you pick?

89. If we were to break up, what would you miss the most about me?

90. What would be an unforgivable sin I could commit against you?

We know we should have conversations but we don’t always know what to say or we forget to ask questions on certain issues.

This article on deep questions to ask your boyfriend will hopefully address that.

deep questions to ask your boyfriend

*This article contains an affiliate link meaning I earn a little commission at no extra cost to you when you make a purchase*

Sharing is caring!