100 Fun Questions To Ask Your Boyfriend For Hearty Time Together

Whether you are a couple of months into your new relationship or have been together for years, this list of fun questions to ask your boyfriend is just perfect!

Dr. Samar Hafeez
Reviewed by DR. SAMAR HAFEEZ , Clinical Psychologist | Written by Aastha Pahadia , Certified Relationship Coach
Updated on Jan 28, 2023 | 10:40 AM IST | 5.4M
Discover the fun questions to ask your boyfriend
Discover the fun questions to ask your boyfriend

There comes a time in everybody's relationship wherein all of you start pondering over the little moments in life that make you happy and how you, as an intimate couple, can share that happiness with each other. “Spending quality time with your loved one is very essential for a relationship to grow into something much more deep and profound. Ongoing mutual and meaningful time spent within a romantic relationship is known to have a positive physical and psychological impact on both partners”, says Dr. Samar Hafeez, a clinical psychologist and certified holistic health and wellness coach. At times, the greatest way to strengthen your loving bond with your partner is to sit down and talk-talk-talk your heart out, ask random questions, discuss silly things, and just have that heartfelt chat with them. This is where this list of fun questions to ask your boyfriend comes in handy!

These funny questions will make you laugh and think and create a fun atmosphere to rebuild a fulfilling relationship. Moreover, they are perfect for getting to know your boyfriend/spouse better. Some of these questions to ask your boyfriend for fun are thought-provoking, interesting, and hilarious, and some are just plain ridiculous! Anyhow, what is guaranteed is probably a gala time with your significant other!

100 Fun Questions To Ask Your Boyfriend When You Are Bored

Fun Questions To Ask Your Boyfriend When You Are Bored

  1. What is the most embarrassing moment you’ve had in front of someone?
  2. What is your favorite joke?
  3. What are your hidden talents?
  4. If I were an ice cream flavor, what flavor would I be?
  5. If we were stranded on a desert island, what three things would you bring with us?
  6. What was the last movie that made you cry?
  7. If you had to put a human brain in a stuffed toy, who would you pick and why?
  8. What are some of your conversation starters?
  9. What is your favorite pair of food and wine? Why do you like it so much?
  10. If we were in a haunted house, what would be the scariest thing for you to see or hear?
  11. If someone tells you a joke and it is not funny, what would you do?
  12. What is the weirdest thing that has ever happened to you while driving (or riding)?
  13. What is your irrational fear?
  14. What kind of animal do you think I am?
  15. If you were an animal, what would you be and why?
  16. What do you think of my good morning texts?
  17. What is the craziest thing you've ever done for love?
  18. If you could have any superpower, what would it be and why?
  19. What was your ideal vacation? Would you take me there?
  20. What was the last thing that made you laugh so hard that you cried (or almost did)?
  21. What is the best thing about being in a relationship with you?
  22. What do you like most about me?
  23. If you had to dress up as food, what would it be?
  24. If we were on a boat, what would you do if I was seasick?
  25. What kind of dream house would make you the happiest?
  26. What is the craziest thing you've ever done for a friend?
  27. If you could be a vegetable, which one would you be? Why?
  28. What is your happiest memory to date?
  29. Which cocktail are you and what am I?
  30. Do you believe in ghosts or spirits or have any paranormal experiences?
  31. Would you rather have wings or a tail? Why?
  32. Have you ever had an embarrassing moment that made it hard for people to look at your face for a while afterward?
  33. Do people tell jokes about your name often?
  34. Can you spell "supercalifragilisticexpialidocious"?
  35. What was the last TV show that made you cry or feel really sad when it ended?
  36. What funny childhood nicknames did your circle of friends call you by?
  37. What makes you procrastinate while working?
  38. What is your guilty pleasure?
  39. If you had to pick unusual animals as pets, which would you pick, and why?
  40. What is your proudest moment to date?

Fun Questions To Ask Your Boyfriend

41. If you had to tuition a junior, which subject would you choose?

42. What is the dumbest thing you have ever said to anyone?

43. What is the best or strangest gift you ever received and given?

44. When do you lose your temper?

45. What is the worst drink you have ever had?

46. What silly things are you proud of doing?

47. What is the weirdest conversation or gossip that you have ever heard?

48. If we had to be an animal couple, which animal pair would we represent?

49. If you could not hire humans as your employees, whom would you prefer?

50. If you could bring to life a fictional character, who would you choose and why?

51. What has been your worst and best date?

52. Who is your favorite celebrity couple?

53. What kind of date would you want to go on with me?

54. If you had to try something cheesy from a Hollywood movie, what would you do?

55. Which conspiracy theory would you like to be a part of? Why?

56. If you become the richest person on Earth, what would you do?

57. Is your "personal" search history safe for anyone to see? Yes, including "incognito mode".

58. What is the weirdest concept of manliness that you have ever heard?

59. If you had to pull a prank on someone, who would you pick?

60. Will you let me experiment with makeup on you?

61. If you had to name yourself after your favorite superhero, what would your name be?

62. If you had to name me after a historical figure, what would my name be?

63. How many times have you drunk-called? To whom? What did you say?

64. What would you rather have - unlimited money (but extreme loneliness) or respect (but bare-minimum money)?

65. If you were asked to vacate your residence immediately, which five things would you take with you?

66. What are the flaws that make you insecure?

67. How often (and why) do you judge people?

68. What, according to you, is my worst quality?

69. Every guy fantasizes about having threesomes. True or False?

70. What is your take on friends with benefits?

71. What makes you grumpy or snobby immediately?

72. Do you tell things you heard about someone to someone else?

73. What makes you complain about things?

74. If you were not into a corporate job, what would you have done rather?

75. What is the best feature of my body?

76. What is my utmost good quality?

77. What is your utmost good quality?

78. If you could change something about your life, what would you change? Why?

79. Is there something that you will never want to change about your life?

80. Would you try drugs even if they were legal?

Fun Questions To Ask Your Boyfriend

81. How will you describe your perfect day?

82. How will you describe your most boring day?

83. What do you prefer doing on a lazy day?

84. Do you think there should be a "no bath on Sunday" rule?

85. If you had to eat only 1 food item for the rest of your life, what would you eat?

86. If I became an ant, would you still love me?

87, How do you think we should solve conflicts?

88. If you find a large sum of money on the ground, what will you do?

89. If you had to make a web series on your life, what would you name it? How many episodes will it have?

90. What are the top 10 things on your bucket list?

91. What are your biggest fears? Why?

92. If we break up someday, would you try to sort things out with me or leave it up to fate?

93. Do you believe in love at first sight?

94. Which Hollywood movie would you like to direct?

95. What are your obsessions?

96. If you had to become a cartoon character, who would you be?

97. If you had to bring back any of the old cartoons, which one would you pick? Why?

98. Did anyone ever try to prank you?

99. On the count of three, you have to name 5 things. 1 2 3, go!

100. How will you describe our relationship in 1 line?


Even after being in a relationship for a while, you will find that there are many things that you probably do not know about your partner. Or there are times that you feel your boyfriend is drifting apart from you. And it can be tough to get to know them better or directly put them on the spot sometimes. This set of fun questions to ask your boyfriend can help you out if you want to get to know your significant other better and will even help you get closer to him. So, are you ready to rekindle the spark and love in your relationship?

ALSO READ: 100+ Great Questions to Ask to Get to Know Someone Better


What topics should couples talk about?
From favorite movies, hopes, dreams, favorite scents, dream jobs, grossest habits, bad experiences, and favorite memories to fears and insecurities, a couple can talk about any topic they are comfortable with.

How do I keep a conversation going?
“Give your partner undivided attention and build active and reflective listening skills, be empathetic and understanding, provide a non-judgemental space for your partner to discuss whatever, focus on the quality of speech and not its quantity, be available and in the present moment with your partner, do not bring up any old conversations or complaints into play”, says Dr. Hafeez. You can also ask questions that are deep, flirty, weird, cute, intimate, creative, embarrassing, and romantic or discuss the relationship deal breakers. You can choose any topic to talk about (depending on the bond you share with the other person) to keep the conversation going.

What can I ask a guy to make him smile?
To make a guy smile, you can either have a deep conversation with him or ask him questions like “If I fall for you, do you promise to catch me?” “I have been so occupied throughout the day. Would you mind distracting me a bit with your smile, baby?” or “I miss you so much, do you also miss me?”.

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About The Author
Aastha Pahadia
Aastha Pahadia
Certified Relationship Coach

Aastha is a certified Relationship coach and she strives to help those who seek expert advice on relationships.



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