Questions to Ask Your Boyfriend: 100 Good Ones for Every Mood

By Jordan Underwood, Founder of Playmate Labs · Last updated: October 2026

The best questions to ask your boyfriend are specific, a little unexpected and easy to answer with a story rather than a feeling. "What's a skill you taught yourself?" gets a better answer than "How are you, really?", and the feelings tend to follow. Below are 100 questions to ask your boyfriend, sorted by mood: getting to know him, fun, deep, the future, flirty and the early days.

None of them are on our main list of questions to ask your partner, so if you've already worked through that, this is a fresh deck. Draw one at random below, or scroll to the section that fits tonight.

Questions to ask your boyfriend to get to know him

Good for the first few months, and surprisingly good after five years. Most of these ask for a memory or a name, which is easier to answer than a feeling and usually more revealing.

1. What's a sound that takes you straight back to your childhood home?
2. Apart from your parents, which adult did you look up to most when you were twelve?
3. What's the best advice a grown-up gave you that you ignored at the time?
4. What were you obsessed with as a teenager: a band, a game, a sport, a person?
5. Which of your mates would you call at 3am, and why them?
6. What's a skill you taught yourself?
7. What's the worst job you've ever had, and what did it teach you?
8. What's a film you can quote almost word for word?
9. As a kid, what did you get told off for most?
10. What are you proud of that has nothing to do with work?
11. What's something you're weirdly particular about?
12. Who in your family are you most like, and do you like that?
13. What's the best meal you've ever eaten, and who were you with?
14. Which place you've lived would you go back to?
15. What's a rule you live by, even if you've never said it out loud?
16. What was the last thing that made you properly belly-laugh?
17. Which hobby did you give up that you secretly miss?
18. What would your friends say is your most annoying habit, and would they be right?
19. What's a small thing that can ruin your whole day?
20. What's a question nobody ever asks you that you wish they would?

Fun questions to ask your boyfriend

For long drives, queues and the bit of the evening when neither of you can pick a film. There are no wrong answers, only indefensible ones.

21. What's your most controversial food opinion?
22. If you went on a TV quiz show, what would your specialist subject be?
23. Which fictional character do you think you'd actually get on with?
24. What's your most useless talent?
25. If you could be brilliant at one sport overnight, which would you pick?
26. What's the most embarrassing song you know every word to?
27. What animal would you be, and what animal would I be?
28. If you had walk-on music every time you entered a room, what would it be?
29. What's the worst haircut you've ever had, and is there photographic evidence?
30. You can only eat one cuisine for the rest of your life. Which one?
31. What would you name a boat if you owned one?
32. Which famous person would you most like to go for a pint with?
33. What's the silliest thing you believed as a child for far too long?
34. Which decade's fashion would you happily wear every day?
35. What's the pettiest thing you've ever done to win a game?
36. If you could only keep three apps on your phone, which three?
37. What's the most random thing you've looked up this week?
38. Which of your relatives would be best on a reality TV show?
39. What's the best thing you've ever found in a charity shop or on the street?
40. What's your karaoke song, and have you ever actually sung it?

If he enjoys these, he'll enjoy our would you rather questions for couples too.

Deep questions to ask your boyfriend

Save these for a calm evening, a walk or a long car journey. Plenty of people find it easier to talk about big things side by side than face to face, so don't worry if the best answers come while you're both looking at the road.

41. What's something you were taught about being a man that you've had to unlearn?
42. When did you last cry, and what set it off?
43. Who do you go to when something is really wrong?
44. Is there a part of your childhood you don't talk about much?
45. Do you find it easier to show love or to say it?
46. What's a mistake you're glad you made?
47. What do you worry about that you think I'd never guess?
48. Which friendship do you miss most, and what happened to it?
49. When do you feel like you're falling short, and what helps?
50. What would you tell your sixteen-year-old self?
51. What does being a good partner mean to you?
52. How did your parents show they loved each other, or didn't?
53. What's the bravest thing you've ever done?
54. What do you find hardest to ask for help with?
55. Is there anything you've never quite forgiven yourself for?
56. When things go wrong, is the voice in your head kind or harsh?
57. What do you think you'd regret not doing?
58. What helps when your head gets loud?

If he goes quiet, let him. A pause usually means he's thinking, not that he's shut down. And answer the question yourself afterwards: it makes it an exchange, not an interview.

Questions to ask your boyfriend about the future

Dreams first, logistics later. These are about the life he wants, not a five-year plan you need to agree on tonight.

59. Where do you picture yourself living when you're sixty?
60. What does a good year look like to you, beyond work?
61. Is there a career you'd still like to try?
62. What do you want to learn properly in the next five years?
63. Do you want to settle in one place or keep moving around?
64. What kind of old man do you want to be?
65. If we had a free month next year, how would you want us to spend it?
66. What do you want to have done by your next big birthday?
67. What would make you feel financially secure, in real terms?
68. Which family tradition would you carry on, and which would you quietly drop?
69. Which of your friends do you think you'll still be close to in twenty years?
70. What do you want your weekends to look like in five years' time?
71. What's a risk you'd like to take while you still can?
72. Long term: a house in the country or a flat in the city, and why?
73. What do you hope we're still doing together when we're old?

Flirty questions to ask your boyfriend

Cheeky, warm and safe to ask in a restaurant. They work over text too, which is where our flirty texts to send your partner come in.

74. When did you first realise you fancied me?
75. What were you nervous about before our first date?
76. What did you tell your mates about me after we first met?
77. What's your favourite thing about my face?
78. Which of my laughs is your favourite?
79. Where would you take me if you wanted to impress me all over again?
80. When was a moment you wanted to kiss me but didn't?
81. If you wrote me a love letter, what would the first line be?
82. What's a nickname you've thought about calling me but never dared?
83. When do you think I look happiest?
84. What's your favourite photo of us, and why that one?
85. Slow dance in the kitchen, or a proper dance floor?
86. What's the most romantic thing you've ever done for anyone?
87. What's something about me you'd brag about to your mates?
88. If tonight were our first date, where would you take me for the last drink?

Questions to ask a new boyfriend

The early weeks are when you learn how someone actually lives. These are light enough for a third date and useful enough to save you a few surprises later.

89. How do you like to spend a Sunday when nobody needs you?
90. Are you a planner or a "let's see what happens" person?
91. What's your relationship with your family like?
92. How do you like to be told when you've annoyed someone?
93. What does a good weekend away look like to you?
94. Are you a texter or a caller?
95. How much time do you like with your friends compared with time as a couple?
96. What's a dealbreaker of yours that people wouldn't expect?
97. What did you learn from your last relationship?
98. How do you show someone you care when words aren't your thing?
99. What's the best way to cheer you up after a rubbish day?
100. What made you say yes to a second date with me?

How to get your boyfriend to actually answer

Plenty of men will chat for an hour about football or work and then go blank at "How do you feel about us?" That's rarely a lack of feeling. More often it's a question that's too abstract, asked at the wrong moment. A few things that help:

• Ask for a story, not a feeling. "What's the bravest thing you've done?" opens the door to how he sees himself without asking him to describe it.
• Pick a side-by-side moment. Cooking, walking the dog, a long drive. Less eye contact, less pressure.
• Go first. Answer the question yourself before or after. It shows the level you're hoping for.
• One question, then follow-ups. "What happened next?" and "How did that feel at the time?" do more than ten new questions.
• No gotchas. If an answer surprises you, be curious about it rather than hurt by it. That's how you get honest answers next time too.
• Make it a game. Taking turns with a deck, a jar or a stack of blocks takes the "we need to talk" feeling away completely.

That last one is the idea behind Nude Stack'd, our date-night stacking game for two: you pull a block, read the matching card, pick one of three levels, or skip it. If you'd rather make your own, our couples Jenga rules and questions show you how, and our guide to couple games at home has plenty that need nothing at all.

Frequently asked questions

What are good questions to ask your boyfriend?

Good questions are specific and easy to answer with a story. "What's a skill you taught yourself?", "Who do you go to when something is really wrong?" and "What would you name a boat?" all work better than "What are you thinking?" Mix one light question with one deeper one, and ask a follow-up before moving on.

What are deep questions to ask your boyfriend?

Deep questions ask about his history, fears and values. Try "What were you taught about being a man that you've had to unlearn?", "What do you find hardest to ask for help with?" or "What do you think you'd regret not doing?" Ask them somewhere relaxed, one at a time, and share your own answer too.

What are cute questions to ask your boyfriend over text?

Short ones he can answer in a line: "When did you first realise you fancied me?", "What's your favourite photo of us?" or "If you wrote me a love letter, what would the first line be?" Keep the bigger questions for when you're together or on a call.

How do I get my boyfriend to open up?

Ask for stories rather than feelings, pick a relaxed side-by-side moment such as a walk or a drive, and go first with your own answer. Follow up with "what happened next?" instead of jumping to a new question, and never punish an honest answer. Turning it into a game takes the pressure off for both of you.

Related Reading

• Questions to Ask Your Partner: 155 Questions for Every Moment
• Questions to Ask Your Girlfriend
• Questions to Ask in a Long Distance Relationship
• Would You Rather Questions for Couples
• Date Night Ideas at Home