70 Questions to Ask Your Boyfriend (Cute, Fun and Deep)

At the start of a relationship, questions come easily because everything is new. A few months or years in, conversations can drift into the same loop: what are we eating, what are we watching, did you see that text. Asking a good question is one of the simplest ways to get out of that loop and learn something new about the person you are with.

Here are 70 questions to ask your boyfriend, grouped by mood. Some are cute, some are silly and some are about the bigger things, like the future and what you both want. You don't need to use them all. Pick a few that fit the moment and let the conversation go wherever it goes.

How to ask without it feeling like an interview

• Pick a relaxed moment. A walk, a drive, a lazy breakfast or a late-night call works better than the middle of a busy day.
• Mix light and deep. Start with something funny before asking about the future.
• Answer too. Every question on this list works both ways. Share your own answer after his.
• Follow up. "Why?" and "What happened next?" are often better than the next question on the list.
• Keep heavier topics for the right time. Questions about money, family or the future are not great over a rushed lunch.

Cute questions to ask your boyfriend

1. What did you think the first time you saw me?
2. When did you realize you liked me?
3. What is your favorite memory of us so far?
4. What is something small I do that you love?
5. Which song makes you think of me?
6. What is your favorite photo of us?
7. What was going through your head on our first date?
8. What nickname would you give me if you had to pick a new one?
9. When do you feel closest to me?
10. What is your favorite way to spend a lazy day together?

Fun questions to ask your boyfriend

11. If you could have any job for one day, what would it be?
12. What is the weirdest food you actually like?
13. Which fictional world would you want to live in?
14. If you had a talk show, who would be your first guest?
15. What would you do with a completely free week?
16. What is the most embarrassing thing that happened to you at school?
17. Which three things would you take to a desert island?
18. What is your most controversial food opinion?
19. If you were an animal, which one would you be?
20. What is the best prank you have ever pulled or seen?

Questions to get to know him better

21. What was your family like when you were growing up?
22. Who was your hero as a kid?
23. What is something you are really proud of that you don't talk about?
24. Which friend has known you the longest?
25. What do you do when you need to recharge?
26. What is a hobby you would love to get into?
27. What is the best advice anyone has given you?
28. What is something you have changed your mind about?
29. What makes you lose track of time?
30. What is a habit you are trying to build or break?

Deep questions to ask your boyfriend

Ask these when you both have time, and be ready to answer them yourself.

31. What does a good relationship look like to you?
32. How do you like to be supported when you are having a hard time?
33. What is something you are scared of that you rarely say out loud?
34. Is there something from your past that still affects you?
35. How do you know when you can trust someone?
36. What do you need more of from me?
37. What is the hardest thing you have ever been through?
38. What do you think we are really good at as a couple?
39. How do you usually deal with arguments, and how would you like to?
40. What makes you feel most loved?

Questions about the future

41. Where do you see yourself in five years?
42. What does your ideal home look like?
43. Is there a city or country you would love to live in?
44. What is one big goal you want to reach?
45. What kind of trip should we take together one day?
46. How do you picture a normal weekday in ten years?
47. What traditions would you like us to have?
48. How important is it for you to live close to family?
49. What is something you want to try before you turn 40?
50. What does "settling down" mean to you?

This or that questions for couples

Quick questions for a car ride or a slow evening. Guess his answer before he says it.

51. Night in or night out?
52. Beach or mountains?
53. Sweet or savory breakfast?
54. Texting or calling?
55. Plan everything or go with the flow?
56. Early mornings or late nights?
57. Dogs or cats?
58. Big party or small dinner with friends?
59. Cook at home or order in?
60. Road trip or flight?

Questions to see how well he knows you

These are the ones to save for a game. Ask him to guess your answer, then see how close he gets.

61. Which cozy night in would I pick?
62. What would I steal from your wardrobe?
63. What kind of gift makes me happiest?
64. How do I want to be looked after when I am sick?
65. What am I like when I am hungry?
66. How do I like to make up after an argument?
67. Where would I go on a spontaneous day trip?
68. Which dessert would I never share with you?
69. What do I do when we watch a movie together?
70. How much do I like to text during the day?

Turn it into a boyfriend quiz

Want a score for those last ten? Our free Boyfriend Quiz lets you answer 10 questions about yourself and send him a link. He guesses each answer, and his score shows up on your scoreboard. Your best friend can take the same quiz, so you can find out who knows you better (he might not enjoy that part).

Afterwards, go through the questions he missed together. Those little surprises are usually where the best conversations start, and they are a good reminder that there is always more to learn about each other.

More ideas for couples

If you want a game you can both play, our list of couples quiz questions has rounds you can use on a date night, and the Couples Quiz works for partners of any kind. For a quiz with friends instead, see our best friend quiz questions.