115 Deep Questions To Ask Your Boyfriend

I’m a big fan of asking thought-provoking questions and then sitting back to enjoy the conversation.

In fact, when I casually mentioned to my partner that I was working on this list of deep questions to ask your boyfriend, he didn’t miss a beat.

“That’s right up your alley!” he blurted out.

He said this because he’s endured countless icebreaker card decks, question games, books, and deep conversation prompts over the years.

And because he’s patient (and a great sport), he hasn’t just humored me— he’s done this with most of my friends and family too.

Depending on his mood, asking him these deep questions is either a fascinating conversation… or absolute torture.

That’s because there are bad questions to ask your boyfriend, and people slip them in all the time without realizing it.

Bad questions shut down connection instead of building it.

They create jealousy, assume blame, invite arguments, or aren’t open-ended enough to spark real conversation.

With my partner, this is especially obvious.

Since he’s an instructional designer who thinks in extremely logical terms, he answers exactly what is asked—no nuance, no sugarcoating.

If the questions are worded poorly, the discussion quickly spirals into analyzing the questions themselves instead of having a real conversation.

And that’s the last thing I want to happen to you.

That’s why I’ve carefully put together this list of deep questions to ask your boyfriend— ones that actually lead to meaningful, open, and engaging conversations. Here you go:

Self-Discovery & Personal Growth

Questions about who you are, what you value and how you’re growing as a person:

1. What kind of person do you want to be, and what values are most important to you?
2. What do you consider your biggest strengths and weaknesses?
3. What’s holding you back from being the person you want to be?
4. How do you think a person reaches full self-acceptance?
5. What is fundamental to building self-confidence?
6. Do you fully understand and appreciate your own worth?
7. When have you questioned yourself or your worth, and why?
8. What is one thing you will never tolerate?
9. Who inspires you to be a better person and why?
10. What’s a personal struggle that you wish I understood better?
11. How have your values changed over the years?
12. In what ways have you grown into the person you want to be, and in what ways haven’t you?
13. What do you like most about yourself?
14. If you could change one thing about yourself, what would it be?
15. What makes you a genuinely good person?

Emotional Intelligence & Vulnerability

Questions that help you understand your emotions, fears, and how you handle tough feelings:

16. Have you ever felt like you weren’t good enough? If so, why?
17. Have you ever felt like you were trying to be someone you’re not? Why?
18. How easily are you influenced by others?
19. How well do you think you know yourself, and what are you still figuring out?
20. If you had unlimited confidence, what would you do differently?
21. In which situations do you feel most confident? Least confident?
22. Do you feel confident about your appearance? If not, why?
23. Do you have insecurities? If so, how do you handle them?
24. What situations make you feel vulnerable?
25. What is your biggest fear, and how do you deal with it?
26. How often do you worry, and what do you worry about?
27. Do you experience anxiety? In what situations, and how do you cope?

Trust & Communication

Questions about how you express yourself, build trust, and handle feedback in relationships.

28. Do you find it difficult to trust people? If so, why?
29. How trustworthy do you think you are?
30. How easy or difficult do you find it to express your feelings?
31. How do you typically respond to criticism?
32. Are you more motivated by praise or criticism?
33. What are you most protective over, and why?
34. How do you know when you can fully trust someone?
35. How do you feel when we argue, and what would help you feel safer in those moments?
36. What’s one thing you struggle to talk about in relationships?
37. What’s one fear you have about being open with me?

Relationships & Love

Questions about what makes a relationship strong, what you need from love, and how you connect as a couple:

38. What’s a way we could grow closer that we haven’t explored yet?
39. How well do you think we handle conflict as a couple?
40. What do you think is our biggest strength as a couple?
41. What’s a little thing I do that means a lot to you?
42. What’s something we used to do that you miss?
43. What’s something I do that makes you feel seen?
44. How do you think we balance independence and togetherness?
45. What’s a compromise you’ve made in our relationship that you feel good about?
46. What are your relationship deal-breakers?
47. What does commitment mean to you?
48. What do you think makes a relationship last?
49. What’s something about our love that feels unique?

MORE: 101 Spicy Questions To Ask Your Boyfriend Tonight

Memories & Life Experiences

Questions that reflect on important moments, lessons learned, and how the past shapes you:

50. What’s a memory of us that always makes you smile?
51. When was the moment you knew you loved me?
52. If you could relive any moment, what would it be and why?
53. What’s the best advice you’ve ever received, and why did it resonate?
54. What’s one thing you’ve never told me but feel safe enough to share now?
55. What’s the best bad decision you’ve ever made?
56. What three events have shaped you the most?
57. What’s one thing you believed about love when you were younger that you see differently now?
58. If you could go back in time and change one decision, would you? Why?

Future Goals & Aspirations

Deep questions to ask your boyfriend about your dreams, goals, and what kind of life and relationship you want to build:

59. What’s a dream you have for our future together?
60. If we could take a spontaneous trip anywhere, where would we go?
61. If we had unlimited time and money, what’s something we would do together?
62. What’s a skill or hobby you’d love for us to learn together?
63. What’s something you hope we never lose in our relationship?
64. What’s the legacy you want our love to leave behind?
65. What’s one new tradition you’d like to start together?
66. If you could write a book, what would it be about?
67. If you could time travel, would you go forward or backward?
68. What’s the best book or movie you’ve ever read/watched, and why?

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Happiness & Mental Well-Being

Interesting questions about what brings you joy, how you handle stress, and what makes life fulfilling:

69. How happy do you think you are in your life right now?
70. What things would make you happier in your life right now?
71. What small things make you smile or laugh?
72. How do you try to bring happiness to others?
73. What’s the best gift you’ve ever received, and why?
74. What motivates you the most in life?
75. How in control do you think we are of our own happiness?
76. What makes you truly happy?

Values & Beliefs

Questions about what matters most to you, your moral compass, and how you see the world:

77. Do you believe everything happens for a reason?
78. How do you define a successful long-term relationship?
79. What is something you’ve always wanted to learn?
80. How much money do you think you need to be happy and free?
81. How do you define success?
82. Do you believe in fate, or do we create our own paths?
83. What social issue matters most to you, and why?
84. What’s one cause that’s close to your heart?

Adventure & Fun

Questions that spark curiosity, playfulness, and excitement about life’s possibilities:

85. If you could live in someone else’s body for a day, who would it be and why?
86. If you could have any job, what would it be?
87. What’s a guilty pleasure no one knows about?
88. If we had to describe our love story in three words, what would they be?
89. If our relationship had a theme song, what would it be?
90. If you had unlimited confidence, what would you do differently?
91. What’s a lesson you had to learn the hard way?
92. What’s a mistake you made multiple times before finally learning?
93. If you could time travel, would you go forward or backward?
94. What’s something spontaneous you’ve always wanted to do?
95. If you only had one day to live, how would you spend it?

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Deep Emotional Connection

Questions that strengthen intimacy, trust, and understanding in a close relationship:

96. When do you feel most emotionally connected to me?
97. How do you like to be comforted when you’re stressed or upset?
98. What’s one thing I do that makes you feel safe?
99. How do you feel about growing older?
100. How do you typically manage stress?
101. What’s something you hope we never lose in our relationship?
102. What’s the biggest lesson you’ve learned about yourself through being with me?
103. How well do you think we support each other?
104. If we ever faced a really big challenge, what would help you stay committed to us?
105. What’s something I do that makes you feel truly loved?
106. If you could describe our love story in three words, what would they be?
107. How do you know when you can fully trust someone?
108. What does love mean to you?
109. What is one thing you’ve never told me but feel safe enough to share now?
110. When have you felt the most emotionally connected to me?
111. What’s one thing you wish I understood better about you?
112. What’s one fear you have about being open with me?
113. What’s a past emotional wound that still affects the way you love?
114. What’s a way we could grow closer that we haven’t explored yet?
115. What’s something about our love that feels unique?

That’s all 115 deep questions to ask your boyfriend.

And remember: you don’t need to ask them back to back like an interrogation.

Just throw a few in when you want something better than another debate about what to watch on Netflix.

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