108 Questions to Ask Your Boyfriend

Pick the Right Question for the Moment

The right question to ask your boyfriend depends on where you are and how much time you have. A deep question in a loud bar gets a joke back. A fun question during a serious talk feels like a dodge.

Where you are	Best group	Why it fits
Car ride or walk	Fun, getting to know you	Side by side, there is less pressure to make eye contact
Texting during the day	Flirty, fun	Short answers work, and he can reply between tasks
Dinner at home	Getting to know you, future	You have time for stories and follow-ups
Quiet night in	Deep, relationship	Private, no clock, no audience
After a hard week	Relationship, light fun	Shows you noticed without asking him to dig deep

Jump to: fun · getting to know you · deep · flirty · future · relationship · how to ask

Fun Questions to Ask Your Boyfriend

Fun questions to ask your boyfriend get him laughing and telling stories, which makes the next, more personal question easier to answer.

1. What is the most useless skill you are proud of?
2. If you could only eat one cuisine for a year, which would you pick?
3. What did you get in trouble for most as a kid?
4. Which cartoon character are you most like?
5. What is the worst haircut you have ever had?
6. If you had a talk show, who would your first three guests be?
7. What opinion do you defend hard even though it does not matter at all?
8. What would your entrance song be?
9. What is the strangest thing you searched for this week?
10. If you could be world-class at one sport overnight, which one?
11. What food do you pretend to like?
12. Which of your friends would survive longest in a zombie movie?
13. What is the best thing you ever bought for under $10?
14. If we swapped jobs for a day, what would go wrong first?
15. What chore would you pay almost anything to never do again?
16. What is your go-to karaoke song?
17. If you opened a restaurant, what would be on the menu?
18. Which animal do you think you could be best friends with?

Getting to Know You Questions

Getting-to-know-you questions fill in the years before you met: his family, his friends, his first jobs and the small habits that made him who he is.

19. What did you want to be at age 10?
20. Who was your best friend growing up, and do you still talk?
21. What smell takes you straight back to childhood?
22. What was your first job, and what did it teach you?
23. Which teacher do you still think about?
24. What were you like in high school?
25. What did your family do that you thought was normal until you left home?
26. Who do you call first with good news?
27. What does a perfect Saturday look like for you?
28. What skill do you want to learn this year?
29. What is the best trip you have ever taken?
30. Which of your friends knows you best?
31. Are you more like your mom or your dad?
32. What movie can you watch over and over?
33. What do you spend money on without guilt?
34. How do you recharge after a long week?
35. What do people get wrong about you when they first meet you?
36. What were you obsessed with last year?

Deep Questions to Ask Your Boyfriend

Deep questions to ask your boyfriend reach his fears, regrets and values, so ask them in private and be ready to answer each one yourself.

37. What are you still trying to forgive yourself for?
38. When did you last cry, and what about?
39. What do you wish your dad had told you?
40. What are you most afraid people will find out about you?
41. When do you feel most like yourself?
42. What belief have you changed your mind about as an adult?
43. What was the hardest year of your life so far?
44. What does being a good man mean to you?
45. What do you need but rarely ask for?
46. Who do you feel you have let down?
47. What part of your childhood shows up in how you act today?
48. What do you think you are here to do?
49. When do you feel lonely, even around people?
50. What compliment has stuck with you the longest?
51. What fear have you outgrown?
52. How do you know when you are not okay?
53. What do you want people to say about you when you are 80?
54. What have you never told anyone in your family?

Some people answer feelings questions with facts. If he answers “When did you last cry?” with a date and nothing else, follow up with “What was going on that week?” A question about events is often the door to the feeling.

Flirty Questions to Ask Your Boyfriend

Flirty questions to ask your boyfriend point back at the two of you: what he noticed, what he remembers and what he likes. All of these stay non-explicit, so they work over text or at a restaurant table.

55. What did you notice about me first?
56. When did you know you wanted a second date?
57. Which outfit of mine do you like most?
58. How do you like me to say hello when I see you?
59. What small thing do I do that drives you crazy in a good way?
60. Where would you take me if money did not matter for one night?
61. What did you think when I first texted you?
62. Which song makes you think of me?
63. What do you like about the way I talk?
64. Do you remember what I wore on our first date?
65. What would our perfect lazy Sunday morning look like?
66. When do you think I look best?
67. What have you wanted to say to me but felt shy about?
68. What is your favorite memory of us that nobody else knows?
69. If you wrote me a note to find in my pocket, what would it say?
70. Which habit of mine did you find cute at the start?
71. Would you rather slow dance in the kitchen or at a wedding?
72. What made you want to kiss me the first time?

Future Questions

Future questions show whether your plans point the same way. Ask them out of curiosity, especially in the first year, and treat every answer as a starting point for talk.

73. Where do you see yourself living in five years?
74. What does your dream home look like?
75. Do you want kids, and if so, when?
76. How do you picture a normal Tuesday ten years from now?
77. What career move would you make if you were not scared?
78. How do you feel about pets?
79. Which family traditions do you want to keep?
80. Which family traditions do you want to drop?
81. Are you more of a saver or a spender?
82. Would you ever move abroad?
83. What do you want to have done by 40?
84. How involved do you want our families to be in our life?
85. What does retirement look like to you?
86. What trip should we take before we turn 50?
87. How would you want to split chores if we lived together?
88. What would you do with a year off?
89. What is one thing you want us to build together?
90. How do you feel about marriage?

Questions About Your Relationship

Questions about your relationship tell you what is working and what he needs, before a small gap turns into an argument.

91. What do I do that makes you feel most loved?
92. When do you feel closest to me?
93. What is one thing I could do more of?
94. How do you like to be comforted when you are upset?
95. What do we argue about that you think we could solve?
96. Do you feel like you can tell me anything?
97. What did you learn from your last relationship?
98. How much alone time do you need in a week?
99. What does cheating mean to you?
100. How do you like to make up after a fight?
101. What about us do you never want to change?
102. Do you feel I listen when you talk about work?
103. How do you show love when words feel hard?
104. What do I do that you have never thanked me for?
105. What do you want our friends to see when they look at us?
106. How can I tell when you need space?
107. Which couple do you admire, and why?
108. Is there anything you have wanted to bring up but have not?

Ask question 99 early. Couples draw the line in different places on texting an ex, flirting or hidden apps, and the what counts as cheating guide shows how widely Americans disagree.

How to Ask So He Keeps Talking

You keep your boyfriend talking by asking one question, then following his answer instead of jumping to the next question. The list gives you a starting point. You learn the most from the follow-up.

Use these five habits:

1. Answer it too. After he answers, give your own answer. A one-sided question night feels like an interview.
2. Follow up twice. Ask “What was that like?” or “What happened next?” before you move on.
3. Go light, then deeper. The 36 questions in a 1997 study by Arthur Aron and colleagues, described by Greater Good in Action at UC Berkeley, started easy and grew more personal. Strangers who took turns with them for about 45 minutes reported more closeness than strangers who made small talk. Copy that order.
4. Allow a pass. Agree that either of you can skip a question with no explanation. People share more when they know they can stop.
5. Never use an answer as ammunition. If he admits a fear tonight and hears it thrown back in a fight next month, he will stop answering.

Timing matters as much as wording. Avoid deep questions when either of you is hungry, tired or just home from work. Side-by-side moments, like driving or cooking together, often get longer answers than sitting across a table.

Small replies count too. The Gottman Institute reports that in a six-year follow-up of newlyweds, couples who stayed married had turned toward each other’s bids for attention about 86% of the time in the lab, against about 33% for couples who divorced. Putting your phone down when he answers is one of those turns.

Questions to Skip or Reword

Some questions shut a conversation down. Skip these, or reword them:

• “Who was your best ex?” It forces a ranking. Ask “What did you learn from your last relationship?” instead.
• “Do you love me more than…?” Any comparison question invites a defensive answer.
• “What is your love language?” It is a fun prompt, but a 2024 review reported by the University of Toronto found little evidence that people have one primary love language. Ask question 91 instead, which gets you the specific answer.
• Questions asked as a test. If you already know the answer you want, say what you want directly. The how to communicate in a relationship guide shows how.

When Questions Are the Wrong Tool

Questions are the wrong tool when you are using them to check up on him. If you suspect he is hiding something, a list of casual questions will make you both more anxious. The signs your boyfriend is cheating guide covers what to look at and how to raise it directly.

Our advice would change if your boyfriend goes quiet or angry whenever you ask anything personal, week after week. A fun question night will not fix that pattern. Name it calmly once, and if it continues, a couples counselor can help you both see it.

Pick three questions to ask your boyfriend from three different groups, save them in your phone, and ask the first one the next time you are in the car together.