105 Cute Romantic Questions to Ask Your Boyfriend

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Conversations are how we learn about people, and nowhere is it more important to have deep and meaningful conversations than when we are dating. As a bonus, asking questions can be a playful and romantic way to really get to know your boyfriend and decide whether he is the ONE. 

But when you’re staring deeply into his gorgeous eyes, you may forget what you want to ask. What now? Luckily, we’ve got you covered with the best romantic questions to ask your boyfriend. 

[Want deeper questions to find out more about your boyfriends personality? Check out this massive post on deep questions to ask.]

What Are the Best Romantic Questions to Ask Your Boyfriend?

The best romantic questions are always cute. By teasing just enough to get hearts beating faster while answers keep each of you entertained and committed, you will be even more in love. Here we have a list of the ultimate cute and romantic questions to ask your partner. These questions should have unique and interesting answers that stimulate further conversation so you can both learn about each other.  

Romantic questions need not be “Do you love me?” “Should we get married?” or “Can you pass me the TV remote?” In fact, romantic questions for your boyfriend should be playful, show commitment, and help you learn about him, while also helping him learn about you.

Why Is It Beneficial to Ask Questions in a Relationship?

Questions are about answers, listening to those answers, and sharing information so you and your partner can get to know each other. Other benefits of asking questions in your relationship are:

  • It builds intimacy – When someone asks you questions, they also reveal part of themselves, and this helps you really see and connect with them. If you are the one asking, you show your partner your vulnerable side by what you ask, and they feel much more empowered to be your intimate partner.
  • Encourages sharing – Ask a question, receive a question. If you’re guarded by nature, or perhaps you’ve been disappointed and betrayed before, asking questions is a great way to learn to trust again. Questions help you share without necessarily volunteering information. Since you ask, your partner feels able to share. 
  • Establish boundaries – Questions help you maintain boundaries. When your partner does something you’re not comfortable with, a question gives them the opportunity to explain, instead of dealing with an accusation of their “wrongdoing.” 
  • Learning your partner’s style of communication – Each of us has a different way of communicating, and each of us speaks a different love language. Using questions, we can learn about each other, discover our communication preferences, and learn to listen to each other.
  • Reveals openness – If you ask a question, it means you really want to know the answer. Asking your partner intimate questions shows you are open to their answers (whatever these may be), that you support them, and will listen to them. Relationship transparency will help your relationship and self-love grow.
  • Builds trust – All relationships are about trust. When someone listens to you, it is easier to trust them. When they ask questions, they are also revealing a part of themselves, and their insecurities are revealed by what they ask and how. Questions build trust as a mutual street you can both use.

Asking cute questions as part of your romance routine will also help foster playfulness, build romance, and help transition to more difficult questions to ask. Questions aren’t always meant to be serious, and you don’t want to feel like you’re constantly being “cross-examined,” nor does your partner want that. Cute questions help introduce some humor and relieve tension.  

105 Cute Romantic Questions to Ask Your Boyfriend

Cute questions are about engaging in conversations. They start a connection and help you both share and get to know each other better. Be sure to use follow-up questions that go further, instead of “yes/no” questions that simply end. 

Family Questions to Make Him Laugh

Be sure to ask for details on these questions, and if he’s shy or awkward, then lead with examples from your own life to help break the ice. 

1. Did you ever have a nickname as a kid? Who gave it to you?

2. If your family had super powers, what would they be?

3. What habit did you have as a kid that was strange, and do you still have it? 

4. Describe your memories of Christmas with your family, and tell me about all the mishaps. 

5. How did your family react when you went on your first date?

6. If you could save your last relationship, what would you have done differently? 

7. What do you cherish most about your childhood?

8. If you have children one day, what would you want their childhood to be like?

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The best romantic questions are always cute.

9. If your childhood home was on fire, what would you save first? Is there something in your childhood you would happily add to the fire?

10. What advice would you give yourself as a five-year-old? What advice would your five-year-old self give you now?

11. What’s your favorite memory of your grandparents? And your least favorite. 

12. How did your parents reprimand you when you were disobedient, and was spanking included (or why not)?

13. What family habit don’t you like, and what family habit would you like to create one day?

14. Your siblings/family are quite wild (or quiet); what’s the worst confession any of them ever made?

15. What’s the most embarrassing moment you ever experienced with your family?

Money Questions to Get Him Thinking

Money is said to be the root of all evil, but it can also be pretty telling about someone. These questions shouldn’t be taken too seriously as they are meant to paint a fun picture of our spending habits, money beliefs, and values. 

16. If you won a million dollars, what would you spend it on?

17. If I won a million dollars, how would you feel about it?

18. Have you ever been flat broke, and how did you get over it?

19. If I lost all my money, how would you feel, and what would you do?

20. What is your favorite guilty pleasure to spend money on?

21. You only have five dollars in your pocket and we’re at the beach. What would you spend it on and why?

22. If I buy you an expensive gift, but it’s something you really don’t like, would you go exchange it for something else or refund it?

23. If you were ever desperate for money, would you consider an “indecent proposal” to bail us out?

24. What did you buy that you regret the most?

25. What’s the best bargain you’ve ever bought?

26. How much was your first ever paycheck and what did you spend it on?

27. If I end up in jail for drinking and driving, would you bail me out, even if it’s 3 a.m.?

28. Would you marry someone (or me) if they were broke?

29. What is the worst investment/spending decision you ever made? How do you make better money decisions now? 

Wine, Women, and Song 

Entertainment and relaxation are important parts of life, and this includes your boyfriend’s past girlfriends. Asking about them can be a little cheeky, while also opening the door to free communication.

30. What’s your personal anthem and why?

31. Who was your first date, and what was she like?

32. Have you ever won a drinking contest, and what did you feel like afterward?

33. What’s your favorite food to eat when you feel sad, and when you feel happy?

34. Do you know the words to “New York, New York,” and can you sing it to me?

35. What kind of drunk are you? What’s the funniest thing you’ve ever done while tipsy?

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Cute questions are about engaging in conversations.

36. How many girlfriends have you had, and what did you like about each of them? 

37. What did you hate about each of your past girlfriends? 

38. If a past girlfriend wanted you back, would you be interested? 

39. Do you have a special talent, like singing, playing a musical instrument, dancing, etc.?

40. On the scale of all your past girlfriends, where do I rate out of 10 and why?

Getting Really Personal

When there’s trust, there’s also honesty, and you may want to get to know your boyfriend more intimately. 

41. What’s your favorite sex position and why?

42. Have you ever not liked sex, and what happened?

43. Is there anything you’re snobbish about?

44. What was the worst dream you’ve ever had?

45. If your movie idol got on the same bus as you, what would you do and would you approach her?

46. Have you ever been really embarrassed by something you did or said?

47. What are your worst fears?

48. What makes you really happy?

49. Have you got a favorite pet peeve?

50. Do you have a bucket list, and what are the top three items?

51. What do you dislike about your family and why?

52. What would you like to achieve in life?

53. Which situations make you feel like you’re not being yourself?

54. Who is your role model?

55. What nickname would you really find sexy if I used it for you?

Romancing Each Other

Romance is about intimacy, flirting, and foreplay, so these questions can help you become more romantic with each other. 

56. What is your most attractive feature?

57. What do you find most attractive about me?

58. Do you believe in love at first sight?

59. Do you believe in soulmates? 

60. Does love scare you?

61. What is your love language? 

62. Which outfit that I wear turns you on?

63. If we have children one day, how would you tell them the story of “how I met your mother?”

64. If you had to choose one part of my body you like the most, what would it be?

65. Which part of your body do you love me touching?

66. When I touch your face, what do you feel?

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Asking cute questions as part of your romance routine will also help foster playfulness, build romance, and help transition to more difficult questions to ask.

67. What is the strangest part of my body you’d like to kiss me on?

68. When we cuddle, what do you like the most: stroking or kissing? 

69. If you had to describe our kissing, and your kiss was a strawberry, what is my kiss like?

70. Which would you prefer, to bathe with me or take a shower with me?

Random Fun Questions

Questions shouldn’t always be serious, sometimes they need to be fun too.

71. If I had something between my teeth at a restaurant, would you say something?

72. Which do you prefer, a Big Mac and extra fries or my famous [home-cooked meal]?

73. If we became cartoon characters, who would we be?

74. What do you see as the best outlet for anger?

75. When you feel really happy about something, what do you usually do to express it?

76. If I was the steering wheel of a car, what car part would you be?

77. If you and I had to swap bodies for a day, what would you do?

78. Do you have any dirty habits you wish you could get rid of?

79. Who was your favorite high school teacher and why?

80. Which teacher at your school did you have a crush on, and what about her turned you on?

81. You’re writing an autobiography of your life; what is it called?

82. There’s one cookie left in the box; would you share it with me, offer me the last cookie, or eat it and tell me the box is empty?

83. If you ever had to eat a part of me, which part would you start with?

84. What book or movie do you think best symbolizes our love? 

85. What pet would you most like to have?

86. If you could be an animal, what animal would you be and why?

Personal Questions

Once you’ve gotten a bit warmed up by asking random questions, you can start really asking those nitty-gritty questions that are both cute and deeply intimate.  

87. How would someone earn your respect?

88. Your house is on fire; what do you save first?

89. Name one childhood toy you loved.

90. Does your body have any strange and unusual things about it, like being double-jointed, having a thumb that dislocates when you want, or odd-shaped toes? 

91. What is one thing you would want to change about your body?

92. Have you ever received some amazing advice, and how did it change you?

93. If you could go anywhere in the world for a week, where would you go and why?

94. What is one character trait you’re working on changing?

95. If you could choose, how would you like to die?

96. What would you like people to remember you for the most?

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Cute questions help introduce some humor and relieve tension.  

97. What truth have you accepted, even if it’s hard?

98. List two things you are proud of in your life, and also two things you hate in your life?

99. What is your favorite word and why?

100. If you were trapped in a building after an earthquake and had enough battery power on your phone to make one call, who would you call? 

101. Which of your hobbies do you like the most, and what does this hobby do for you?

102. If you had to be reincarnated, who would you like to come back as?

103. Would you rather win the lottery or get a promotion at work?

104. What is your earliest childhood memory?

105. What is the first thing you remember about me?

Final Thoughts on Cute Romantic Questions to Ask Your Boyfriend

Cute questions are always fun to answer, and when you throw a bit of romance in the mix, you have a winning combination to learn more about each other and grow together as a couple. When asking questions, always consider whether the question is one you would be willing to answer too, and if you ask, listen to what your partner is saying and what is being said between the lines. 

People don’t always articulate their thoughts well, especially when you dive deep. But when you love someone, you will always listen, hear, and feel their answers.  If you’re all out of cute questions to ask your boyfriend, you can always read up on some fun things to do with your friends and your boyfriend too.

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