101 Cute Questions to Ask Your Boyfriend - SimplyTogether (2024)

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Looking for cute questions to ask your boyfriend to make him express things and fall in love with you more?

In this article, I’ll give you lots of ideas of various things you can talk with him about.

I’ll divide this list into a few sections:

• Cute Questions to Ask Your Boyfriend
• Cute and Flirty Questions to Ask Your Boyfriend
• Romantic Questions to Ask Your Boyfriend
• Deep Questions to Ask Your Boyfriend
• Cute Questions to Ask Your Boyfriend Over Text

But before jumping into the particular cute things you can ask him, I first want to outline a very important principle when it comes to this!

This is something, many other relationship experts tent to overlook, but it can make a world of difference in your relationship.

When asking your boyfriend cute questions, try to make it about him and not about yourself.

Asking your boyfriend things that are revolving all around you will make you come across as self-absorbed and needy.

This is why, you want to avoid saying things like: “What do you like most about me?” or “Do you think about me during the day?”.

Shifting your focus to him and asking him genuine questions, on the other hand, will make him perceive you as caring and will inevitably deepen his emotional attachment towards you.

All the examples listed below fit these criteria.

Cute Questions to Ask Your Boyfriend

This is a list of lighthearted, charming things to ask a guy. They are slightly flirty but in an unassuming, innocent way. They are the perfect thing to say as an icebreaker or even when you’re just bored.

There are many things you can do to make your partner love you more. Asking him these kinds of questions is one of them!

1. Do you have a favorite moment in our relationship?

2. Do you prefer: beach or mountains?

3. What are you looking for in a woman?

4. Is there any food you would give up your relationship for?

5. What do you usually do when you’re bored?

6. Who inspires you to be a better person?

7. What makes you laugh more than anything?

8. What’s an activity you’d really like to do with me that we haven’t done so far?

9. If you could describe yourself with three words, what would they be?

10. What’s your favorite season?

11. If you could live anywhere in the world, where would it be?

12. What movie would you like us to watch together?

13. If you won the lottery tomorrow, what would be the first thing you buy?

14. What do you do to cheer yourself up?

15. Did you send an awkward text to someone by mistake?

16. What was the last crazy adventure you went on last you went on?

17. What would you do tomorrow if it were your last day on Earth?

18. Do you have any secret talents?

19. What were you like as a kid?

20. What’s the most spontaneous thing you’ve ever done?

Cute and Flirty Questions to Ask Your Boyfriend

These questions will definitely heat things up between the two of you. They are juicy, flirty (but not overly explicit) things to ask your boyfriend to tease him a little.

Beware, exchanges of this type will likely lead to more than just talking….

Asking a guy these questions will definitely make him want you more.

21. Do you prefer being the big spoon or the little spoon?

22. Who was your first kiss, and how was it?

23. What is your wildest fantasy?

24. What are you most attracted to in a woman?

25. Have you ever been caught doing something you shouldn’t have been doing?

26. What do you think about public display of affection?

27. What do you like to do the most when you’re alone?

28. Have you ever skinny-dipped?

29. What’s your opinion on kissing in public?

30. What’s your favorite type of women’s underwear?

31. What do you think would happen if we were stuck in a room for 24 hours together?

32. If you could be a girl for a day, what’s the first thing you’d do?

33. What’s the funniest pickup line you’ve ever tried?

34. Have you ever found someone attractive who you really shouldn’t?

35. Do you prefer to make the first move?

36. Do you prefer kissing or cuddling?

37. What is it about you, I’m so drawn to?

38. What are you thinking right now?

39. Am I your type?

40. Truth or dare?

Romantic Questions to Ask Your Boyfriend

The aim of these romantic questions is to trigger butterflies in his stomach as well as in yours. Asking your boyfriend these questions will make him get in touch with his feelings for you.

There will be love in the air, both of you can definitely deeply enjoy!

A word of caution, though: some guys get frightened by romance. But don’t let this discourage you. All the questions listed below are guy approved, low-key romantic type.

Plus, you might just need to warm your boyfriend up with some flirting or by telling him that you love him beforehand. (This way you can get his guard down a little…)

41. Do you believe in true love?

42. What’s your idea of a perfect date?

43. Would you move across the world to be with someone you love?

44. In one sentence, how would you sum up romance?

45. What’s your favorite romantic moment in a movie and why?

46. Who was your first crush?

47. How many times have you been in love?

48. What is your idea of a romantic honeymoon destination?

49. How would you define love?

50 What made you fall for me?

51. Is there such a thing as being too much in love?

52. If the house was on fire, what three things would you save?

53. How can I be a better girlfriend for you?

54. What is your idea of the perfect romantic gift?

55 Guess what I like about you the most?

56. Do you believe there’s one person you’re ‘meant’ to be with?

57. Do you believe in fate? Destiny?

58. Where is your favorite place to be with me?

59. What’s your favorite way to receive affection?

60. If we could go anywhere together right now, where would you want to go?

Deep Questions to Ask Your Boyfriend

All the questions below are cute, but also meaningful and deep at the same time. They will make you feel emotionally closer to your boyfriend and will help you gain more of his trust.

You will also learn new things about him and likely feel more connected because of this exchange.

They are all great questions that will make any date much more exciting and memorable.

61. What quality do you like most about yourself?

62. Is there something that you used to do that you loved, but you’ve now stopped doing?

63. If you could tell yourself one thing 10 years ago, what would it be?

64. Is there something about love that scares you?

65. What’s your biggest deal-breaker in a relationship?

66. What are you most proud of?

67. Are you strangely sentimental about any objects you own?

68. What’s the best advice you’ve ever received?

69. How do you think your closest friends would describe you?

70. What is your biggest fear in life?

71. What is the kindest thing someone has ever done for you?

72. Do you think there’s such a thing as the ‘right’ person for you?

73. What’s the hardest thing you’ve had to overcome in life?

74. If you could ask me anything, what would it be?

75. What’s the most valuable thing in your life?

76. How did you like growing up?

77. What’s your greatest passion in life?

78. What would you like our shared goals to be this year?

79. In what ways do you feel loved by me?

80. What is something that not many people know about you?

Cute Questions to Ask Your Boyfriend Over Text

These are playful, slightly flirty but unassuming questions. They are safe to send to your boyfriend, your crush, or even a guy who is fighting his feelings for you.

They are perfect as conversation starters, but can also be used to get more of his attention.

81. What are you thinking about right now?

82. What’s your “go to” video or GIF for a laugh?

83. How many questions can you answer in just pictures?

84. What app on your phone do you think I should get?

85. What is your favorite meme?

86. Do you ever text and drive?

87. If I sent you a picture right now, what would you want to see?

88. Wanna Netflix and chill?

89. What song do you play most often?

90. What’s the worst text that you accidentally sent?

91. How about dinner at my place?

92. What is the most interesting thing you have on you or near you right now? Send me a pic of it.

93. What’s the funniest picture you have on your phone?

94. How many texts do you normally send in a day?

95. What is the perfect way to ask someone out?

96. What’s the most ridiculous thing you’ve seen online recently?

97. Is there an App you think I should download?

98. What’s the funniest thing that someone could spend money on / buy on the internet?

99. What would you love to be called – sexy, charming, or smart?

100. Would you rather wake up tomorrow as the opposite sex or 50 years older?

101. What’s the cutest picture you have on your phone?

Hope you found what you were looking for here, and you now have plenty of cute things to ask your boyfriend over text or next time you’re hanging out with him.

But in case you need even more inspiration, you can check out my husband’s post:

50 Flirty Texts to Make Him Think About You All Day Long

These are all guy approved, safe to send texts that will make any guy crazy about you.

Thank you for reading and if you have any questions about these questions, be sure to leave them down below, and I’ll get back to you!

Karolina