151 Random Funny Questions to Ask a Guy

Funny questions to ask a guy

So, what are some of the funniest questions you can ask a guy

Humor is a very attractive quality to find in both men and women.

There is even research out there on humor, saying that women like men who have humor and make them laugh.

Men enjoy women who laugh at their jokes.

Research goes on to say that even though both men and women enjoy a “good sense of humor” in someone they are looking for as a potential partner, they differ in what they understand it to mean.


Robert Provine analyzed over 3000 singles and found that women could describe their good humor appreciation while men were likelier to produce good humor abilities.

What Will I Learn?

You want to keep the fire going in your relationship

It will help to get to know him better.

See how much he laughs!

In a relationship, keeping your boyfriend interested in you is very important.

He might get bored during your conversations – but with these funny questions, you might even revive the spark and cause some fire again.

He just might get to see another exciting side of you!

Open-ended type questions are much better than those simple yes and no type questions.

It is because these can lead to great conversations and exciting places.

It will depend on what you have been wondering about for some time or what topics are being pursued in your texting thread, and what topics you will choose.

But we have helped you by providing a very handy list for you to check out.

If you have your eyes on a guy, you will find these ideal icebreakers.

Making a new crush laugh is an excellent way to win his heart, so enjoy these, and have great fun and conversations!

151 Funny Questions to Ask a Guy That He’ll be Splitting His Sides

Guy conversing with a girl

Funny food questions

Use these fun questions to ease the tension about where you are going to eat or what food you will prepare.

Do you even like the same food?

Food is always something to bond over.

1. “Have you ever laughed so hard that your drink came out of your nose?”

2. “If you could only eat one food for the rest of your life, what would it be?”

3. “What is the weirdest thing you’ve ever eaten?”

4. “What is the grossest thing you’ve eaten?”

5. “If you were a new pizza flavor, what would you be?”

6. “What is your dream crazy ice cream flavor?”

7. “Do you have any weird eating habits?”

8. “What food combo do you love that most people would probably hate?”

Funny bedroom questions

You’re ‘gonna surprise your boyfriend with these questions.

He’s going to like this fun side of you.

It won’t be such a good idea, though, to send him these at work otherwise, he might send you an NSFW – you know, Not Safe For Work.

Instead save these for a romantic night.

9. “What is the weirdest thing that’s happened to you in bed?”

10. “What personal body part do you like most?”

11. “Have you ever farted loudly during an intimate moment?”

12. “What was your worst kiss like?”

13. “What is the dumbest thing you’ve done in the bedroom that initially seemed like a great idea?”

14. “What happened during the worst date of your life?”

15. “If you woke up one day as a woman, what’s the first thing you’d do?”

16. “If you could only use one position in bed for the rest of your life, what would it be?”

17. “What is the weirdest place you’ve done the deed in?”

18. “Have you ever gotten a cramp when trying a position?”

19. “Do you think pillow fights are fun or too silly?”

20. “Would you wear a onesie to bed?”

Embarrassing Funny Questions

Sometimes mistakes we make can be pretty funny.

Laugh with your boyfriend, not at him.

Help him see the bright side of every funny situation.

If you ask your boyfriend questions and he opens up about stuff he doesn’t usually talk about, then you can’t clamp up and get coy with him when he asks similar questions and expects answers!

21. “Has anybody ever walked in on you naked?”

22. “Have you ever burped or farted loudly when the whole room was quiet?”

23. “Have you ever called somebody by a completely wrong name?”

24. “Have you ever walked into a glass wall or door?”

25. “What is your biggest guilty pleasure?”

26. “What song do you love that everyone else thinks is annoying?”

27. “Is there a TV show you love to watch even though it might be dull or shallow?”

28. “Have you ever released a smelly fart and then blamed it on someone else?”

29. “Have you ever accidentally broken something and then hidden the evidence?”

30. “Have you dropped food on white clothes while eating out?”

31. “Have you ever ripped your pants in public?”

32. “Have you ever gone out without deodorant and then only remembered when you smelled something funny?”

33. “Have you ever tripped over your shoelaces?”

34. “Have you ever walked into the wrong bathroom at the mall?”

35. “Have you ever walked in on someone else while they were naked?”

36. “Has anybody ever walked in on you while you were busy in the bedroom?”

37. “Has milk or any other drink come out of your nose when you sneezed?”

38. “What is the most ridiculous outfit you’ve ever had to wear in public?”

39. “What is the most embarrassing thing you’ve said to someone you found hot?”

40. “Have you ever accidentally entered an occupied toilet you thought was empty?”

41. “What is the most embarrassing thing you’ve ever been caught doing?”

42. “Have you ever caught someone else doing something embarrassing?”

Asking funny questions about school days

This is an excellent opportunity to find out what kind of guy your boyfriend was when he was at school and before you met him.

Sometimes when you listen to a childhood that was completely different from yours, you might see a side to your boyfriend you never even knew about and it might be an eye-opening experience.

Opening up and sharing more about yourselves will help you to see if you have the same dreams, ideals, and humor!

43. “Did you ever fart loudly in class?”

44. “Did you ever call your teacher mom or dad?”

45. “Were you ever caught texting in class?”

46. “Did you usually text people in class?”

47. “What was your favorite subject in school?”

48. “What was your worst subject and why?”

49. “What was the dumbest project you ever had to do?”

50. “Were there any awful school performances you had to join?”

51. “What was your dumbest field trip like?”

52. “Did you ever have a crush on a teacher?”

53. “Did your crushes ever find out that you liked them if you didn’t tell them directly?”

54. “Did you ever do something silly in front of your class crush?”

55. “Did you ever walk into the wrong classroom?”

56. “Have you ever laughed loudly when the whole class was quiet?”

57. “Did you ever have food fights in the cafeteria?”

58. “Were you good at gym classes?”

59. “Did you ever make a huge mess during art classes?”

60. “Did you ever skip class to do something fun?”

61. “Did you ever go to school drunk or hungover?”

…. And work

66. “Have you ever accidentally called your boss or a co-worker mom or dad?”

67. “Have you ever called someone in your workplace the name of an old teacher?”

68. “Do you think you could or would hang out with your boss outside of work?”

69. “Would you get ridiculously drunk with your boss?”

70. “Could you imagine what it would be like to date your boss?”

71. ‟What is the grossest job you would do for a million dollars per year?”

72. “Have you ever farted loudly during an important meeting?”

73. “Have you ever heard someone fart during a meeting and then pretend like nothing was wrong or stinky?”

74. “Have you ever caught your co-workers doing something against the rules in the office? What did you do about it?”

75. “Have you ever joined your co-workers in doing something completely against your office rules? Were you guys caught in the act?”

76. “What is the wildest thing you’ve seen happen at a company party or outing?”

77. “Did you ever think you were texting someone else something funny, but then it was sent to your boss?”

Funny Relationship Questions

A great way to make your relationship more robust is to laugh at it!

You two will have more fun and avoid getting bored with each other, and you’ll also gain more knowledge on how your partner views your relationship.

78. “What movie do you think best describes our love story?”

79. “If we were to make a movie about us, which actor would play you? And which actress would play my part?”

80. “Did you ever think you were texting me, but then the message went to someone else?”

81. “What were your thoughts when I first did something gross before you?”

82. “Are there any gross or weird things that you’re too shy to do in front of me?”

83. “What is your weirdest habit that I haven’t seen yet?”

84. “What cheesy song would you pick for our theme song?”

85. “What cliché romantic trope do you secretly want us to check off our bucket list?”

86. “Do you have any cheesy date ideas that you’ve been dying to go on?”

87. “What was going through your mind when you first did something gross in front of me?”

88. “What do you think is my weirdest or most unusual habit?”

89. “What part of a kids’ movie completely scared you?”

90. “On a boring to insanely cheesy scale, how romantic do you think you are? Why?”

91. “If you are marooned on a deserted island, which Hollywood actress would you like to be with?”

92. “Did you have a nickname that you hated when you were a child?”

93. “Is there anything you would like to change in me?”

94. “Which comic character do you think I resemble?”

95. “If you are given an option to be born as an animal or bird, what would it be?”

96. “Did you had a funny ambition when you were a kid?”

97. “Would you like to try some kind of adventure sport? Which one?”

98. “Who is your favorite superhero?”

99. “What is the best compliment that you ever received from a girl?”

100. “If you found a magic lamp, what would be your three romantic wishes?”

Sharing is more important than you might have known

If you have just been texting a new boyfriend, for instance, and you have used many of these fabulous texts, the time will come when you also want to meet this guy and get an ideal first date done.

It will be time to face the guy you have dreamed of for a long time.

But of course, even with texting, there is the chance that something could go wrong.

Remember that things never go as planned, but also remember you have humor on your side, that, and relaxation.

The key to good conversations is to keep going.

In the beginning, it will be good to have a plan, like knowing what questions you will ask.

You will also need to avoid some.

By sharing different experiences, secrets, and facts, you will both be more prosperous for each other.

That’s the whole point of a good relationship – it’s making each other better people and making a good impression on each other.

Here are some golden rules to read about which will make conversing with a guy go smoother.

Here are some general important tips:

  • Never interrogate him
  • Have a good arsenal of tricky and baffling but non-confrontational questions!
  • Be prepared for one of your questions to backfire!

Some more fun, interesting questions that he might laugh out and enjoy

101. “What would you bring to a desert island if you could only bring three things?”

102. “What celebrity would you like to meet and why? Do they deserve admiration?”

103. “Do you think people who star in a reality show have self-respect?”

104. “Without concrete evidence, how can you dispute the existence of a higher force?”

105. “Cats or dogs?”

106. “How do you think the world will look in 30 years?”

107. “Will there ever be a WWIII?”

108. “If there is one meal you could eat for the rest of your life, what would it be?”

109. “What meal wouldn’t you eat even for a million dollars?”

110. “If you won $10 million on the lottery, what would you do with it?”

111. “If you could live in one period of history, which period would it be?”

112. “Care to sink your teeth into my meal a bit?”

113. “Care to share an Italian kiss or more than a few?”

114. “Can I trust you with a dirty little secret?” (Here, you can share something significant or dirty. But, remember a good tool here is the anti-climax. Like you say something medial and then laugh about it as a joke. You will soon see if he has a good sense of humor).

115. “Care to go with me on an adventure? Let’s say rock-climbing or sailing. How does that sound?”

116. “Which part of your body would say is your favorite?”

117. “When it comes to the female body, which kind of look do you appreciate?”

118. “I’m sorry for looking at you hard, it’s not that you’re gorgeous or anything. Can you forgive me?”

119. “Do you think you can maintain eye contact longer than me?”

120. “How would you feel if we moved our location to somewhere more intimate?”

121. “How much takes it to get you slightly tipsy?”

122. “Would you see me home? Just in case….”

123. “Whose place do you think has a better interior design? Wanna find out?”

124. “How do you feel about a nutritious breakfast after a long night?”

125. “Do you have a map? Because I think I got lost inside of your eyes.”

126. “Sorry, I get carried away by just looking at you.”

127. “Is it legal to stare as much as I stare at you?”

128. “What section of your body do you hate the most?”

129. “You’re like a walking inspiration for dirty thoughts….”

These types of questions are always needed in a relationship.

So whether it’s your first date or you have some relationship years behind you, you can always find a good use for these.

Men sometimes can be more reluctant to be themselves when they don’t know you.

But with a couple of funny questions, he will start to feel more comfortable as he senses you have humor and wit.

130. “Can you impersonate a celebrity? What would they think if they heard you? Come on, don’t be shy!”

131. “Would you join a reality show like Big Brother? Would you be serious to win, or would you want to have fun?”

132. “What was your worst embarrassment ever? How did you live it up?”

133. “Have you ever eaten something disgusting but only found out later about it?”

134. “What was your funniest drunken adventure? How did you manage to return home?”

135. “If you could throw up on one person, who would it be?”

136. “What was the funniest joke you’ve ever heard?”

137. “What words sound sexy to you?”

138. “What is your most embarrassing dream?”

139. “What was the worst situation you were ever naked in?”

140. “If someone painted a portrait of you, what would you be wearing and how would you pose, etc., and what else would be in the painting with you?”

141. “What’s the difference between a woman and a microwave?

A guy will press all the buttons on the microwave to get it heated.”

So amusing you are …

142. “Why is Spider-Man a bad boyfriend? – He’s super clingy.

143. “What do a boyfriend and mascara have in common? – They both run at the first sign of emotion.”

144. “What do a good employee and a boyfriend have in common? – They’re always coming early.

145. “Why are boyfriends like parking spaces? – The good ones are already taken!

146. “Guess what’s on the menu? – Me-n-u.

147. “Why did the boyfriend give his girlfriend a medieval battle uniform to polish while he went to the bar?” – He said she always wanted “a night in, shining armor.”

148. “Are you French? – Because Eiffel for you.”

149. “Why do painters always fall for their models? Because they love them with all of their art.”

150. “Are you a banana? – Because I find you a-peeling.”

151. “Is your name WiFi? – Because I’m feeling a connection.”

152. “Knock, knock. Who’s there? Candice. Candice, who? Candice be love that I am feeling right now?”

152. “Knock, knock. Who’s there? Honeydew. Honeydew, who? Honeydew, you know how much I love you?”

153. “What did one volcano say to the other volcano? I lava you.”

154. “Why should you never marry a tennis player? Because love means nothing to them!”

156. “How did the telephone propose to its girlfriend? He gave her a ring.”

157. “What is your favorite movie quote?”

Frequently Asked Questions(FAQs)

What can I text a guy to make him smile when he thinks of me?

First, it totally depends on the guy; there are no rules when it comes to these types of things. Nevertheless, there are things you can text to your crush to make him smile.

Tell him you wish you could be together or tell him your life has brightened up so much since he came into it.

How can I make him really miss me over text?

The thing is that what works for one person may not necessarily score you points with someone else.

You could tell him that you can’t stop thinking about him, and then add something like ‘thanks for always being there for me’.

Or if you are deep in a relationship already, you could simply ask him if he wants to mess your bed up with you tonight!

Will sending him humorous texts keep me on his mind?

As long as he’s human, being humorous with him keeps him guessing and is one of a handful of ways to keep you on his mind.

You also have to work on yourself and look good too for a guy; we not talking model stuff here, but show off your best features, and of course, let your humorous side shine as well!

Be yourself as much as possible, without trying to fit into a box of what you think a girlfriend should be like for a guy.

Is laughing a sign of attraction?

Check out your crush’s laugh. Sometimes just the way they laugh can let you know they are interested in you.

People tend to laugh more when they are trying to show they are positive, happy, and interested in you.

When you make jokes or comments, and they giggle and laugh back, it could be a sign they are nervous too, but nevertheless interested.

Do guys like it when girls laugh at them?

Research studies show that men and women alike like a “good sense of humor” in a potential partner, but they do differ in what they like.

Women usually go for men who make them laugh, but men tend to like women who laugh at their jokes.


Speaking to a guy you adore and trying to keep him interested can be pretty daunting for a gal.

That nervousness can come from fearing failure.

But relax!

The fun and excitement of talking to your dream guy are taking steps into the unknown.

But the truth is that he will feel equally as nervous as you if you meet for the first time.

It’s just that guys seem to have the knack of not showing their nervousness as much.

But have courage, and don’t be nervous to let him know that you care for him and want to get to know him.

Remember, this article is about bringing some humor into your relationship, whether a new one or an old one.

Because when you maintain a sense of humor, you will see how much better you cope!

Sure, you get conversation ruts, but don’t overthink them when they occur.

Just pope another question, like, “How was your day yesterday?”

That can keep things going again.

Just remember to relax and don’t view this getting-to-know-him-better situation or adding some humor into your relationships as a life-or-death situation.

What you want to show him is the real you.

Remember, too, that communication is not only about words.

You can talk fake, but your body language will give you away.

Don’t ask specific questions too soon; don’t even necessarily lean on them to get you through.

Just let the conversation flow, and you might not even need them.

Keep the relationship questions ready, but only when you’re sure that you and your crush are moving in that direction.

Too soon, and you might just spook the poor guy. Just be flirty and funny, and he will appreciate it.

Sexual comments will only be appropriate at the appropriate time.

The beginning is usually the scariest part, but once you are over the bumps, watch and see how smoothly humorous texting and, later on, a date goes! 

Good luck!