Questions to Ask Your Boyfriend: 67 Ideas, Light to Deep

What are good questions to ask your boyfriend?

The best ones invite a story instead of a yes or no. "What was the best part of your week?" gets you further than "Was your week good?", because he has to choose a moment and tell you why. Pick the group below that fits your mood, ask two or three, and stay with one answer for a while before you move on.

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Why asking questions makes a relationship stronger

Questions work because they make talk personal on purpose. In a 1997 study, Arthur Aron and colleagues had pairs of strangers answer questions that grew more personal every few minutes. After 45 minutes, those pairs felt closer than pairs who stuck to small talk.

Follow-up questions matter too. A 2017 Harvard study found that people who asked more questions, especially follow-ups, were liked more by the person they talked to.

Many couples hold back because deep talk feels risky. In a 2022 set of experiments, people expected deep conversations to be more awkward than they were. Afterwards they felt closer to their partner than people who had made shallow talk.

That also holds when you have been together for years. People change, and the answer to "What do you want from this year?" is not the same as it was two years ago.

Fun and easy questions to ask your boyfriend

Start here if you are new together, or if the last few weeks have been all logistics. They are quick to answer, and they show how he sees the world.

1. What's the best part of your week so far?
2. What's a small thing that always puts you in a good mood?
3. What's a meal you could eat every week and never get tired of?
4. What's something you're into that most people don't know about?
5. If we had a free Saturday with no plans, what would you want to do?
6. What's the funniest thing that happened to you as a kid?
7. Which song takes you straight back to a certain time in your life?
8. What's a skill you wish you had?
9. What's a place you've never been but think about often?
10. What's something I do that makes you smile?

Questions about his daily life and habits

Daily habits shape a shared life more than big dreams do. These questions show what his normal looks like and what he needs to feel good.

11. What does a good day look like for you, from morning to night?
12. How do you like to recharge after a hard week: alone, with friends, or with me?
13. What's a routine you'd hate to give up?
14. How do you feel about plans: do you like them locked in or loose?
15. What part of your job do you enjoy, and what part drains you?
16. What do you do when you're stressed and don't say anything?
17. How much alone time do you need in a normal week?
18. What's something small I could do that would make your week easier?

Questions about love and feeling cared for

People feel loved in different ways, and guessing is how small hurts start. These questions let him tell you instead.

19. When do you feel most loved by me?
20. What's something I've done that you still think about?
21. How do you like to be comforted when you've had a bad day: advice, a hug, or just company?
22. Do you prefer words, time together, help with tasks, gifts or touch? What's your top one?
23. What's a way you show care that I might miss?
24. Is there something you'd like to hear from me more often?
25. What makes you feel closest to me?
26. What was the best date or day we've had so far, and what made it good?
27. What's something you've wanted to ask me but haven't?
28. What does a good relationship look like to you day to day?

Questions about talking, trust and conflict

How a couple handles disagreement says more than how they handle good days. Ask these when things are calm, not in the middle of an argument.

29. What's the best way for me to bring up something that bothers me?
30. When we disagree, do you need space first or do you want to talk it through right away?
31. What's something I do in an argument that makes it harder for you?
32. What's something you do in an argument that you'd like to do differently?
33. What helps you trust someone?
34. How do you feel about checking in during the day: more, less, or about right?
35. Is there anything we've been avoiding talking about?
36. How do you want us to make up after a fight?

Questions about money

Money is one of the topics couples argue about most, and one of the topics new couples skip. You don't need a spreadsheet to start. Try these first.

37. What did you learn about money growing up, on purpose or by accident?
38. Are you more of a saver or a spender?
39. What's something you'd happily spend too much on?
40. How should a couple split costs: evenly, by income, or case by case?
41. Is there a money goal you're working toward right now?
42. What would make you feel financially safe?

Questions about family and friends

The people he grew up with shape what he expects from a partner. Go gently here, because family can be a sore topic for some.

43. Who in your family are you closest to, and why?
44. What was a family tradition you loved as a kid?
45. What do you want to keep from how you were raised, and what do you want to do differently?
46. How often do you want to see your family, and how often do you want us to?
47. Which friends matter most to you, and how can I get to know them better?
48. How do you picture holidays: big gatherings or something quiet?

Questions about the future

These show whether you are heading toward the same kind of life. They matter most once you've been together a while and want to know where it could go.

49. Where do you see us in five years?
50. Where do you want to live, and how flexible are you about it?
51. How important is your career to you compared with the rest of your life?
52. Do you want kids, and if yes, how many and when?
53. How do you feel about marriage?
54. What's one thing you want us to do together in the next year?

Low-key nosy questions

These are the questions you are curious about and rarely ask out loud. Ask them with a smile, and keep your own answer ready.

55. What did you assume about me from my Instagram before we talked?
56. What was the first "green flag" you noticed in me?
57. What's a tiny detail about me that you remembered weirdly well?
58. What do you think I'm secretly sensitive about?
59. What do I do when I'm trying to look unbothered?
60. What song would you secretly add to our shared playlist to flirt?
61. If we got stuck in an elevator, what would you do first?

Deep questions to ask your boyfriend

These take trust. Pick a quiet moment, put your phones away, and share your own answer too.

62. What's something you're afraid of that you rarely say out loud?
63. What's a time you changed your mind about something important?
64. What's a part of your past that shaped who you are now?
65. What do you need more of in your life right now?
66. When do you feel most like yourself?
67. What's one thing you hope I'll never stop doing?

How to ask follow-up questions

The list gets the talk started. The follow-up is where you learn something new.

• Pick one detail from his answer and ask about it: "You said you need alone time after a hard week. What does that look like for you?"
• Ask how it felt, not only what happened: "What was that like for you?"
• Share your own answer, so it feels like a conversation and not an interview.
• Let a pause sit for a few seconds; people often add the most honest part after it.
• When he shares good news, ask for the details instead of a quick "nice". Research by Shelly Gable and colleagues linked that kind of warm, curious reaction to closer, happier couples.
• If he'd rather skip a question, let it go. You can try again another day.

If you want more ideas, see our page of deep conversation questions. For questions that work with anyone, from a first date to an old friend, see questions to ask to get to know someone. For a list sorted by how long you've been together, see questions to ask your girlfriend.

When questions are not enough

Questions are for getting closer, not for settling a fight that keeps coming back. If the same argument returns week after week, a couples counsellor or licensed therapist can help you both. If you ever feel unsafe with a partner, call the free, confidential National Domestic Violence Hotline at 1-800-799-7233, or 911 in an emergency, and see our trust and safety page.

Summary

Pick a group, ask a few questions, and spend most of the time on his answers. People change, so ask your favorite question again in six months and compare. Next, try questions to ask to get to know someone, the stage-by-stage questions to ask your girlfriend, or first date ideas.