relationships

60 Fun and Illuminating Questions to Ask Your Boyfriend

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In terms of a romantic partner, it’s wonderful to find someone with whom you can share a comfortable silence. Someone who can sit by your side while you think, or not think. Someone you can just be present with. But, of course, you don’t want comfortable silence all the time. For those moments when you want to get closer through conversation, we’ve gathered a list of 60 illuminating questions to ask your boyfriend in order to get to know him a little better.

Relationship Questions

1. Do you want children?

2. Do you want to get married?

3. What do you think the most important element is in maintaining a relationship?

4. What is the No. 1 thing you look for in a partner?

5. What is your favorite thing to do on a date?

6. What is the most romantic place you’ve ever visited?

7. If you want children, how many children do you want?

8. Have you ever been cheated on?

9. What is the best gift you’ve ever given a partner?

10. What is your favorite love song?

11. What is your favorite date night movie?

12. Would you prefer to cook a romantic dinner, or do the romantic dishes?

13. When do you think is the right time to say “I love you”?

14. Do you think fighting in a relationship is healthy, or do you think it should be avoided?

15. What is something important you’ve learned from another couple?

16. What is a mistake you’ve made in a relationship in the past that you don’t want to repeat?

17. What do you think is your best attribute as a boyfriend?

18. Are you friends with your exes?

19. Have you ever had your heart broken?

20. How can you tell you’re really comfortable with someone?

Fun Questions

21. Do you have any hidden talents?

22. If you could meet one celebrity, who would it be?

23. If you could relive one day in your life, what day would you choose?

24. Would you ever go skydiving?

25. Have you ever been afraid of a ghost?

26. What was your best Halloween costume?

27. What was your favorite school lunch as a kid?

28. What is your favorite Simpsons joke?

29. If you could live inside the world of one TV show, which would you choose?

30. If you have a billion dollars, what do you think your life would be like?

31. What is your favorite scent?

32. What is your favorite outfit?

33. If you could change your name to anything, would you change it, and what would you change it to?

34. If you could suddenly be very good at something without having to put any effort into getting good at it, what would it be?

35. What is a book or movie you’ve always lied about having read or seen?

36. What career do you wish you could have?

37. If you could go to the moon, would you?

38. Do you think aliens exist?

39. Do you think you would do better or worse on the SATs if you had to take them now?

40. What is your favorite meal of all time?

41. What cartoon character do you think is the hottest of all time?

42. What is your most controversial movie-related opinion?

43. Do you think dogs go to heaven?

44. What is the hottest you’ve ever looked?

45. Who do you think is the MVP, LeBron or Giannis?

Dangerous Questions

46. If you could change one thing about me what would it be?

47. Who do you think has it harder: men or women?

48. Who is the most beautiful person you can think of?

49. Can you explain to me the process of menstruation and why it occurs?

50. Can you tell me what accounts for the sun appearing to rise and set?

51. Can you name ten authors who are not men?

52. Do you still text with any of your exes?

53. Have you ever cheated on anyone, and do you feel the phrase “once a cheater, always a cheater” is true or false?

54. How do you feel about Elizabeth Warren and why?

55. What is the best outfit you’ve ever seen me wear?

56. What is the funniest thing I’ve ever said to you?

57. What is your favorite thing about me?

58. Do you think I’m stronger in my career or stronger in my personal life?

59. Would you rather be a stay-at-home parent or a working parent and why?

60. Does the idea of someone having dinner on the table for you every night at 6 p.m. sound good to you? Why or why not?

60 Questions to Ask Your Boyfriend to Bring You Closer