100+ Quirky Yet Romantic Questions To Ask Your Boyfriend To Make Him Laugh

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romantic questions to ask your boyfriend to make him laugh
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As Victor Borge quotes, “Laughter is the shortest distance between two people.” It is often said that couples who laugh together, last together! You can spice up your love life with the help of these top 100 romantic questions to ask your boyfriend to make him laugh that we’ve listed here in this article. Remember, fun intimate questions to ask your partner are the easiest way to bond with your partner.

And getting to know the sense of humor of your beloved is a part of strengthening your relationship. Studies have proven that a healthy relationship has ‘laughter’ as its core essence. When a guy says you make him laugh, well, then you are definitely on the right track. But if you still struggle to come up with random funny questions to ask a guy, we’re right by your side to help!

You can make a list of freaky questions for him, and we bet it will prove fruitful in striking up a rapport with your special someone. We have a long list of questions to get to know your significant other, some saucy questions to ask, questions to ask in a new relationship, and a bunch of quirky and dirty questions to ask a guy to make him laugh hysterically. So, let’s dive into the world of giggles and chuckles with your ‘boo’.

100+ Quirky Questions To Make Him Smile and Laugh


Finding out romantic situations to involve your partner can be tiresome sometimes. Nevertheless, if you have humor, you have won half the game and are bound to win the race to your man’s heart. When you and a guy laugh together, it boosts your connection, chemistry, and commitment.

Researchers have emphasized that “shared laughter signals that they see the world in the same way.” It wouldn’t matter if you have a new relationship or if you’ve been in the thick and thin for 10 years. Cute romantic questions to ask your boyfriend are brilliant conversation starters, and if you ever feel there’s a lack of communication, you can back on this to rejuvenate your connection.

dirty questions to ask a guy to make him laugh
What are some flirty questions to ask your boyfriend

There are some really weird questions to ask boyfriends that are considered part of a romantic gesture. Such questions are a fun way to get to know the best version of your bae. And now, you don’t need to cook up questions in your own mind, because here is a list of some cute romantic questions to ask your boyfriend to make him laugh:

Trick questions to ask your boyfriend for some laughs

As crafty and cunning as it might sound, trick questions to ask your boyfriend are truly an awesome way to playfully cross some lines. You can ask him about his deepest and darkest truths, but with a jolly tone. These kinds of relationship questions can embark romantic chats, giving the right balance of amusement and sobriety. The drill is to ask some tricky questions while being lighthearted and aiming entirely on ‘how to make my boyfriend laugh’.

Related Reading: How To Be Romantic On Phone – 15 Tips To Get That Right

The discussion can range from random questions to silly yet sly ones. The perks of romantic questions to ask your boyfriend to make him laugh is that you get to enjoy his wit, humor, and make him stutter before he speaks. He might even shy away from some questions, trying to escape the tension-building questions, but at the end, when he answers them, it will be a treat for you.

We have dug into several questions to put him in a hilariously compromised state. So, let us have a look at the perfect blend of humorous, foxy, and crazy questions to ask your partner:

1. What is the most embarrassing moment of your life?

2. What was the most ridiculous fashion trend that you followed?

3. Tell me about the silliest thing you believed as a child.

4. If you came with a warning label, what would it say?

5. What are the lamest dad jokes you’ve heard?

6. What is one fictional character that you found relatable and funny?

7. Who is the celebrity crush you’ve daydreamed about?

8. What can be the most embarrassing thing you would do to win someone over?

9. What’s the craziest thing you’ve done in a serious relationship?

10. What is your favorite memory of an exciting date?

11. If you had a chance to live in a fairy tale, which princess or prince would you be?

12. Show me two pictures that put you in a bad mood.

13. Which cartoon character would you love to impersonate?

14. What is the funniest movie you’ve watched to date?

15. What do you think is the most embarrassing thing you did as an ex?

16. If you were to enact a scene from a romantic comedy movie, which would it be?

17. What can be the theme song of your life?

18. What’s an obscure hobby of yours that you think is an undetachable part of your personality?

19. Describe your happiest childhood memory.

20. Do you remember an interesting conversation with the wrong person?

21. Is your love language singing romantic songs or romantic dinners?

22. What was your dream job as a child?

23. Tell me the funniest thing about your most adored fictional character.

24. What is your notion of romantic trips and exciting dates?

Related Reading: Travel For Two: Tips For Planning Exotic Couples Trip

25. What is the most memorable moment with your best friend?

26. Do you remember the most embarrassing thing you’ve done along with your best friend?

Some questions in the list above contain absurd ideas, while some can make your man think outside the box and use his intellect. There are many rare questions that make it to the top of the list of funny things to ask your lover. Such questions add meaning to conversations too.
Just remember to avoid some daunting questions which may put him in a state of discomfort. The whole idea behind this questionnaire is to be able to help you spend a splendid time with him, and not intimidate him with heavy quizzes. However, comparing his exes, asking for a proposal, and asking political questions should be firmly avoided.

Dirty questions to ask a guy to make him laugh

Couples often get bored of the dull and repetitive conversations between them. One fun way to give a plot twist to your love story is by trying out these romantic questions to ask your boyfriend to make him laugh. The one-stop solution for all your distressed questions, such as, “What to talk with bf at night romantically?” and “What are some new relationship questions to ask him?” is here. You can start by asking these amazing, spicy questions.


Dirty questions are like double-edged swords which have the potential to infuse hilarity and hotness simultaneously. Exploring sexual compatibility by asking some downright naughty questions is considered one great take. His responses to these saucy quizzes can create a storm of erotic desires within you.

Related Reading: 20 Funny Gifts For Boyfriend That’ll Put A Smile On His Face

We’ve got a bunch of sexual questions to ask your boyfriend to make him laugh. Interestingly, 99% of guys blush when asked these questions. So, without further delay, let’s look at some kinky questions to ignite his libido:

27. What is the weirdest thing you like about your celebrity crush?

28. Have you gone skinny dipping with someone?

29. Who is your favorite porn star and why?

30. Do you have a favorite guilty pleasure movie? Name it.

31. What is the wildest fantasy you’ve had for a celebrity crush?

32. Tell me the weirdest thing you’ve done in bed.

33. If you were down for a one-night stand, who would it be with? A stranger or a friend?

34. Have you ever done a one night stand?

35. What is the most outrageous lie you’ve told your best friend?

36. Show me the weirdest thing from your search history.

37. In your opinion, does playing video games together count as a romantic gesture?

On Romance

38. What’s the craziest thing you’ve seen in a romantic comedy movie that you’d try in real life?

39. Tell me the cheesiest pick-up line that you remember at this instant.

40. Would you prefer deep questions or dirty questions on a date night?

41. If you were to pick a role model from reality TV for a hook-up, who would it be?

42. Have you ever thought of kissing your best friend?

43. What is your favorite sex position?

44. Have you ever been caught making out?

45. What do you consider the weirdest thing about your appearance?

46. What’s one romantic song to be played while making out?

47. Tell me the most embarrassing thing a girl has ever asked you.

Realted Reading: 35 Awkward Questions To Ask A Guy (Some Are Embarrassing!)

48. What is the most horrific yet silliest thing you’ve experienced alone?

49. Have your parents ever caught you drooling over your favorite fictional character?

50. Describe the craziest thing you’ve done to ask a girl out.

51. Do you remember an incident when you made a fool of yourself in front of your best friend?

52. What is the most awkward place you got laid in?

Juicy questions to ask your boyfriend for some laughs

Whenever you wonder, “What are some flirty questions to ask your boyfriend?”, it simply shows that you’re willing to keep the relationship alive and happening. And there is no better way to spice up one’s relationship than by trying out these fun questions to ask a man with a hint of hidden naughtiness. Who doesn’t want to create a happy couple space for themselves where a natural pull keeps you both excited and turned on?

Men organically tend to love a relationship where there is shared laughter, intimacy, and romance. After a hectic day at work, a couple needs to have their private time, and these juicy questions to ask your boyfriend serves as that happy pill. The inner satisfaction that comes with the knowledge that you make him laugh a lot is enough to make your day.

The list of romantic questions to ask your boyfriend to make him laugh is vast, and might include the funniest things, such as bizarre questions about topics you can only discuss with your boyfriend over the phone, smutty scenarios, or even about embarrassing childhood memories. So, if you ever find your relationship in a slump, sit with him and try asking him the juicy set of questions listed below:

53. Do you prefer ‘vanilla sex’ or are you the wild kind?

54. Are you a balloon? Because I want to blow you.

55. Is there an intimate scene you want to reenact with me?

56. Would stripping turn you on?

57. Have you dreamt naughtily of me?

Realted Reading: What Does It Mean When You Dream About Your Crush?

58. Explain the hot and wet dream you’ve recently had.

59. What is the wildest and weirdest thing you can imagine yourself doing to me?

60. What is your most controversial opinion about love and sex?

61. Tell me the most embarrassing thing you used to believe about a historical figure.

62. If you weren’t a religious person, what sin would you first commit?

63. What are some juiciest personal questions you’ve been asked?

64. Do you imagine me naked? If yes,how often?

65. How do you feel when I whisper your name sexily?

66. What do you prefer: spanking or choking?

Related Reading: Addictive Flirty Texting: 120 Texts That Will Make Him Want You More

67. Have you tried kissing in a movie theater?

68. What do you call me when your friends are around?

69. Did you ever have a friend with benefits?

70. Describe what a passionate kiss means to you.

71. How long should foreplay last according to you?

72. When did you lose your virginity?

73. What is the one thing you want me to do to you?

74. Do you have random questions in your mind, like what color lingerie am I wearing today?

75. What are your thoughts about roleplay in the bedroom?

76. How often would you like us to have sex?

77. Do you like it when I pull your hair?

78. If you could choose my clothes in the bedroom, what would you do?

Flirty questions to ask your boyfriend

This is yet another collection of questions in the category of cheesy questions for boyfriends. The motive here is to make your man smile and give him a memory of a lifetime. In the stressful world, where people hardly even manage to make time for themselves, ensure some chuckles and mischief together. If communication is the head of a secure relationship, humor and playfulness are the heart of it.

Flirting is basically an art that takes skills and finesse. If you are one of those who often google ‘What are some flirty questions to ask your boyfriend?,’ then this bit is for you. We have a perfectly curated array of enticingly sweet questions to ask a guy that will make him flushed and rekindle your romance.

cute romantic questions to ask your boyfriend
99% of guys blush when asked this question

So, be ready to ask some alluring questions to make him fall in love all over again. These flirtatious and romantic questions to ask your boyfriend to make him laugh are possibly the answer to ‘What to talk with bf at night?’ So, discover some fantasies with giggles. Here is the list of some handpicked flirty questions for him:

79. What is one family tradition of yours that you can imagine me practicing?

80. Am I your favorite snack?

81. What is a romantic gesture you’d like to see in your future wedding?’

82. If given a chance, will you spend a day without underwear?

83. If you met your celebrity crush, would you still choose me?

84. Explain the sequence of your shower routine.

85. What has been your biggest romantic failure?

86. Do you sleep hugging your pillow and will I be allowed to replace it?

Related Reading: 12 Unmistakable Signs It’s Time To Kiss A Girl

87. In your opinion, what’s the sexiest fruit?

88. Would you get high on vodka, whiskey, or me?

89. If you were to call me by a sexy name in bed, what would you choose?

90. If loving you were a full-time job, would you hire me?

91. Right now, at this moment, do you prefer a kiss or a hug?

92. What is your sexiest body part according to you?

93. What is my sexiest body part according to you?

94. Do you believe in love at first sight or should I walk past you again?

95. Do you think I have feelings for you?

96. If you proposed to me now, what words would you say?

97. Do I match the qualities you’d imagined to have in your girlfriend?

98. Would you be surprised if I kissed you right now?

99. Tell me your turn-ons.

100. Would you mind sleeping naked?

101. Do you feel butterflies when I lean toward you?

102. Do you realize how sexy you look when you smirk playfully?

Realted Reading: 50 Compliments For Men That Make Them Happy

103. Have you ever stolen anything? Of course, other than my heart.

104. How would you feel if I kissed you right now?

The right kind of questions asked at the right moment effectively elevate the compatibility of a couple. You can customize the questions for different occasions to get cozy with your boyfriend. Make sure to get hold of the flow and analyze his humor. The questions shouldn’t appear like a questionnaire but should be an addition to playful moments of shared laughter. Remember that 99% of guys blush when asked these questions related to their love life and fun moments.

So, let the sizzle take over and be ready to ask crazy questions, listen to his funny answers, reveal fantasies and secrets, and fire up the romance! Unwinding with your partner is the perfect gift after a long day of work. So, without giving a second thought to it, try these questions out. You may not realize it right away, but you are creating memories to relish forever. A day spent without laughter is a day wasted. As Marcus Aurelius rightly said, “Very little is needed to make a happy life.”

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