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100 Romantic Questions to Ask Your Boyfriend to Make Him Laugh

Asking questions is the best way to get to know someone, particularly a new boyfriend! Here are 100 romantic questions to ask your boyfriend to make him laugh. Read more ⇣
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Written By Erica
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I'm Erica. I love to help people in their relationships and spiritual lives. I've been through a lot of ups and downs, and I want to share my insights with you.
100 romantic questions to ask your boyfriend to make him laugh

Often in relationships, couples run out of things to talk about. And when there’s nothing new to talk about, people fill the void with the same questions over and over again.

We’ve all done this, it’s human nature. But why not try something different?

Whether you just started dating or you want to keep the spark alive, making your boyfriend laugh keeps the romance and passion alive

Questions are one of the best ways to get to know someone, and especially a new boyfriend. What’s even better is adding a bit of humor to your questions to encourage laughs during the getting-to-know-you process.

You know what they say – when you make someone laugh, their heart is yours forever. With all of this being said, I’ve come up with 100 romantic questions to ask your boyfriend to make him laugh.

You should be able to keep the chemistry alive or start a conversation on any one of your date nights with these questions.

100 Romantic Questions to Ask Your Boyfriend to Make Him Laugh

  1. Has someone ever walked in on you while having sex?
  2. Have you ever gone skinny dipping?
  3. What was your first kiss like?
  4. What is your love language?
  5. What are your biggest guilty pleasures?
  6. What is the best piece of advice you have ever received?
  7. Do you consider yourself an introvert or an extrovert?
  8. What is the silliest pickup line you’ve ever used?
  9. What was your dumbest injury?
  10. What was your most awkward date like?
  11. What was the funniest movie you’ve ever seen?
  12. What is your least favorite app that you can’t stop using?
  13. What is your least favorite word?
  14. Have you ever freaked out while meeting someone famous?
  15. How many days without a shower would you be okay with?
  16. What is worse during a kiss – a sneeze or a cough?
  17. Which song do you always refuse you like, because it’s embarrassing but you really enjoy it?
  18. In a zombie apocalypse, if a kiss could make those zombies humans again, would you do it? 
  19. What’s the worst thing your parents have ever caught you doing?
  20. Would you rather have bionic arms or bionic legs?
  21. Which Hogwarts house would the Sorting Hat most likely put you in?
  22. You are about to kick some serious butt, what song comes on as your soundtrack?
  23. Would you rather dance a jig in front of people or dance naked alone?
  24. Has anyone ever walked in on you naked?
  25. What’s something that you are weirdly competitive about?
  26. Why do we call it lipstick if it doesn’t stick our lips together? 
  27. Why do we call cold things “chilled”, meanwhile chilies are called hot? 
  28. If you could create a new holiday that doesn’t exist, which one would it be?
  29. What’s the silliest way you’ve ever injured yourself?
  30. If you had an opportunity to ask your pet 1 question, what it would be?
  31. If you could replace grass with anything you want, what would you choose?
  32. Do you think blind people can see dreams?
  33. Name what sounds like a compliment but it’s actually an insult.
  34. If you could dip anything into chocolate and eat it, what would it be?
  35. Would you rather go on a date with someone who does cheesy magic tricks the entire time, or go on a date with someone who tries to sell you the beach body protein shakes at the end of the date?
  36. What high-level job do you think you could lie your way into with no experience and no one would notice?
  37. What’s one show, movie, or book, you’re embarrassed to admit you enjoy?
  38. What’s a fashion trend you used to rock but now totally regret?
  39. If you were given the chance to marry any fictional character, who would it be?
  40. What is the first law you would change if you were president?
  41. Would you rather only wear Crocs for the rest of your life or only watch Katherine Heigl movies for the next six months?
  42. Would you rather only wear Crocs for the rest of your life or only watch Katherine Heigl movies for the next six months?
  43. What is the worst name you can think of to give your future child?
  44. What’s the most paranormal thing that has ever happened to you?
  45. What would be the worst bio for a dating app?
  46. If your pet could talk, what is the one thing that it can say to ruin your life?
  47. Do you think blind people can see dreams?
  48. If mysteries are unsolved cases, then why do we call them “unsolved mysteries”? 
  49. Do penguins have knees?
  50. If coffee wasn’t legal, what would it be called on the black market?
  51. If the last thing you ate is the only thing you can eat for the rest of your life, how soon will you die?
  52. What was the worst date you’ve ever been on?
  53. If you had the chance to live on Mars, but could never come back, would you do it?
  54. If a piece of gum is 10 calories, how does it work, having 10 calories while chewing or swallowing it?
  55. Is cereal included in the soup category?
  56. If buddha was a girl, would you ask her out?
  57. If it was your last day on earth, would you tell a joke or would you say a prayer?
  58. If a ghost told you to go to hell, what will be your response?
  59. If you had to choose between a donkey, a cow, or a giraffe as a pet, what would be your choice?
  60. Would you rather eat a whole stick of butter or drink a whole bottle of maple syrup? 
  61. Would you sleep with a 700-pound cow if it cost you your life?
  62. Would you name your cat Jabba the Butt if you had one?
  63. How long do you think you would last in the Hunger Games?
  64. Why do men have nipples?
  65. Would you rather be able to only whisper or only shout everything?
  66. What would be the creepiest thing you could say while passing by a stranger on the street?
  67. What was your silliest solution when the toilet wasn’t flushing in someone else’s house?
  68. What is that normal thing for society that you don’t support?
  69. What is that normal thing for society that you don’t support?
  70. What is the smell you like, but it is usually awful for everyone?
  71. Which fruit do you find sexy?
  72. What is the worse name for a feminine product you have ever heard of?
  73. Does any of the seven dwarfs look like you?
  74. Do you think funerals should have stand-up comedy performances?
  75. If a Smurf starts to choke, what color will it become?
  76. If a doctor has a heart attack during surgery, who will other doctors and nurses take care of first?
  77. Why are pizzas placed in a square delivery box?
  78. Have you ever had an imaginary friend; do you still have one?
  79. How many ants are necessary to lift a whale?
  80. If you were Willy Wonka, what flavored gum would you make first? 
  81. If you had 1 billion $ and just 30 mins, what would you do?
  82. If you found out that Hogwarts is real and you’re a magician, what spell would you like to try first?
  83. Would you rather dance a jig in front of people or dance naked alone?
  84. What’s the best WiFi name you’ve seen?
  85. What’s the stupidest tattoo you’ve got after a party when you were drunk?
  86. If you could dis-invent one thing, what it would be?
  87. What was your first-ever email address or screen name?
  88. Would you rather eat jalapeños with every meal for the rest of your life or a raw egg every morning?
  89. What’s your go-to lie when playing “two truths or a lie”?
  90. People who don’t return grocery carts: heroes or villains?
  91. Do you think cavemen had nightmares about cavewomen?
  92. How many chickens would it take to kill an elephant?
  93. Who would win in a fight between Superman and Batman?
  94. What would you rather have to deal with: Have no nose, but have really good smelling fingers? Or be blind but have a really nice smile?
  95. What would you rather have; an arm that regenerates every month, or legs that grow back every month?
  96. What is the most inappropriate object in your fridge?
  97. In three people you hate the most which one would you choose to kill, marry and kiss?
  98. If you had to choose between brushing your teeth or wiping your butt, which one would you choose to do for life?
  99. If you were arrested without explanation, what would your friends and family think you’ve done?
  100. If life was like a musical, people start dancing and singing out of nowhere, what would you do?


Almost all of us, who live in this busy world, is tense and suffer from different kinds of stress. However, a little bit of romance is what we actually require at times. 

No matter how long you’ve been together, there will be times when your relationship feels like a routine. So, every now and then, ask some questions to make the conversation more interesting. 

Although it may sound awkward at the start, you’ll find that this technique can help you understand each other better and deepen your love for each other. Enjoy and have fun!

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