150+ Deep Questions To Ask Your Boyfriend About Your Relationship

If you’re like me, the main reason you want to ask about your relationship is to feel closer and strengthen your connection.

The problem is, asking the wrong question can often turn into an argument instead of the kind of discussion that brings you closer. As I have found out the hard way.

That’s why having the right deep questions to ask your boyfriend about your relationship matters.

The best deep questions to ask your boyfriend are thoughtful but not heavy. They give him room to share what he thinks and feels without putting him on the defensive.

They aren’t about grievances or past criticism, they are about learning more about what he thinks about your life together– past, present and future.

Instead of creating tension, you will create a conversation that makes you both feel more seen, appreciated, and connected.

Asking him these questions will help build closeness so you can enjoy the deeper connection you’re both looking for. Here you go:

Memories and Reflection Questions to Ask

1. What first drew you to me when we met?
2. When you think back to the start of our relationship, what stands out to you?
3. What’s one of your favorite memories we’ve shared so far?
4. When did you first realize you felt comfortable around me?
5. When you think back on our relationship so far, what moments stand out most to you?
6. When you think about your happiest times with me, what comes to mind?
7. What’s a memory from your childhood you’d like me to know more about?
8. What’s a moment you’d like to relive just for the fun of it?
9. What’s a time you’ve felt really connected to me?
10. When have you felt especially proud of us as a couple?
11. What song reminds you of love or relationships?
12. What’s a little thing from our early days together that still makes you smile?
13. What memory of us always feels vivid to you?
14. When you think about the first time we spent time together, what do you remember most?
15. What’s something we did once that you’d like to do again?

Everyday Life Together

16. What kinds of things make you feel loved in a relationship?
17. When you’re stressed, what usually helps you feel better?
18. How do you like to balance independence and closeness in a relationship?
19. How do you usually feel most appreciated?
20. What do you notice most about the way we show care for each other?
21. What everyday moments do you enjoy sharing with me?
22. What’s your favorite way to spend quality time together?
23. What do you enjoy about the way we spend weekends or free time?
24. How do you like to start the day together?
25. How do you like to unwind at the end of the day?
26. What do you enjoy about watching movies or shows together?
27. What do you enjoy most about our private little routines?
28. What makes time at home feel special to you?
29. What do you think makes an evening feel cozy?
30. How do you feel when we take a break from screens and just talk?
31. What do you enjoy about sharing life with someone?
32. What helps you feel at ease when we’re apart?
33. How do you like to share good news with someone close to you?
34. How do you feel when we cook, eat, or share meals together?
35. What makes you feel most connected during daily routines?
36. What do you enjoy about our conversations?
37. What kind of atmosphere makes you feel most relaxed at home?
38. What do you think makes time together feel meaningful?
39. When do you feel most relaxed with me?
40. What makes you look forward to spending time with someone?
41. What’s something simple that always brightens your day?
42. What do you enjoy about running errands or doing everyday things together?
43. What makes a lazy day with me feel special?
44. What little routine of ours do you secretly like most?

Fun and Adventure

46. What role does playfulness have in keeping a relationship strong?
47. What kinds of adventures sound fun to share together?
48. What’s something you’ve always wanted to try with a partner?
49. What’s a place nearby you’d like us to explore together?
50. What do you enjoy about taking walks or being outdoors with me?
51. What’s a place you’d love for us to visit together someday?
52. What do you enjoy about taking trips, even short ones?
53. How do you feel about doing spontaneous things as a couple?
54. What’s a small tradition you’d like to create together?
55. What kinds of conversations feel the most fun to you?
56. What makes a weekend feel perfect in your eyes?
57. What do you enjoy about making plans together?
58. How do you feel about trying new foods or cooking experiments together?
59. What’s something you’d like us to learn as a couple?
60. How do you feel when we share new experiences?
61. What’s something new you’d like to try together?
62. What’s something simple that feels like luxury to you?
63. What’s a fun goal you’d like us to set together?
64. What do you enjoy about taking day trips or short getaways?
65. What makes a vacation unforgettable to you?

Connection and Closeness Questions to Ask Your Boyfriend About Your Relationship

66. What does being “a team” in a relationship mean to you?
67. What kinds of things help you feel most connected in a relationship?
68. What do you think makes a relationship feel supportive?
69. What helps you feel safe opening up about something personal?
70. When do you feel most at ease with me?
71. What do you think helps couples keep curiosity about each other alive?
72. What helps you feel connected even in silence?
73. What makes you feel most understood?
74. What makes you feel truly listened to?
75. What helps you feel close to someone even during busy times?
76. What helps you feel calm when life gets hectic?
77. What do you enjoy about how we keep laughter alive?
78. What’s a simple everyday moment with me that you cherish?
79. What kinds of things make you feel close to someone?
80. What makes a relationship feel steady and dependable to you?
81. How do you feel when we spend quiet time together without distractions?
82. What do you enjoy about sitting in silence with me?
83. What kind of gestures make you feel safe?
84. What makes you feel cared for emotionally?
85. What helps you feel supported during difficult times?

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Communication and Understanding

86. What do you think makes disagreements easier to work through?
87. What does trust mean to you?
88. What helps you feel respected in a relationship?
89. What do you think makes a good listener in a relationship?
90. What do you enjoy most about the way we talk through ideas?
91. How do you think it goes when we work together on a project side-by-side? 
92. What do you like about how we communicate with each other?
93. What do you dislike about how we communicate with each other?
94. What do you notice about how couples adapt to each other’s needs?
95. What do you think helps people stay connected long-term?
96. What do you think keeps relationships fun and playful?
97. What do you think people learn from being in relationships?
98. How do you feel about mixing routines with surprises?
99. What makes you feel proud to be in a relationship?
100. What do you notice first when you think about someone you love?
101. How do you like to reconnect after being busy or distracted?
102. What do you think makes conversations flow easily?
103. How do you prefer to share your feelings?
104. What helps you open up when something is on your mind?
105. What do you appreciate about honest conversations?
106. What makes talking about the future exciting to you?

Romance and Affection

106. What’s a small gesture that feels romantic to you?
107. How do you feel about showing affection in public?
108. What makes you feel thought of when we’re apart?
109. How do you like affection to be shown in public?
110. What little habits or quirks do you secretly enjoy in someone you love?
111. What kinds of things make you feel cared for in everyday life?
112. What helps you feel cared for in little ways?
113. What’s something simple that always feels romantic to you?
114. How do you feel about leaving notes or little reminders of affection?
115. What kinds of surprises do you enjoy?
116. What do you enjoy most about the way we show up for each other day-to-day?
117. What do you enjoy about the way I make you laugh?
118. What’s your favorite way to relax with me?
119. What makes time together feel unforgettable to you?
120. What makes romance feel genuine to you?
121. What’s something playful that makes you feel close?
122. How do you like to be kissed?
123. What’s a small romantic gesture you’ve always loved?
124. What makes intimacy feel safe to you?
125. What do you enjoy most about slow moments together?

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Future and Dreams

126. When you picture us in the future, what comes to mind?
127. What kind of future experiences would you like to share with me?
128. What’s something you’d like to experience in the next few years?
129. What kinds of things make you feel inspired about the future?
130. What do you enjoy about planning something together?
131. How do you like to mark anniversaries or special dates?
132. How do you like to celebrate special occasions?
133. How do you like to mark the change of seasons together?
134. What kind of traditions would you like to have as a couple?
135. What’s something you’d like to look back on years from now and be glad we did?
136. What kinds of dreams do you think are exciting to share with a partner?
137. What’s something you’d love for us to create together?
138. What does commitment look like to you?
139. What does “being in love” mean to you?
140. How would you describe what love means to you?
141. What would you like our life to feel like 10 years from now?
142. What’s a place in the world you’d love us to see together?
143. What makes the idea of a shared future exciting to you?
144. What goals would you like us to support each other in?
145. How do you imagine us celebrating milestones down the road?

Future & Big Picture Questions to Ask Your Boyfriend

146. What kind of home do you picture us in someday?
147. What values feel most important to carry into the future?
148. What adventures do you hope we’ll still be having years from now?
149. What traditions would you love to start that last a lifetime?
150. What makes you feel hopeful about us?
151. Are you interested in marriage and future commitment?
152. Do you want (more) children? How do you see yourself in the context of having a family?

There you are. A whole list of deep questions to ask your boyfriend about your relationship that won’t accidentally start World War III at the dinner table.

Pick a few, try them out, and see what happens. You might end up with a deeper connection… or at least a story you can laugh about later.

Either way, it’ll be a better conversation than arguing about whose turn it is to do the dishes.

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