101+ Funny Questions To Ask A Guy To Make Him Laugh

Last updated on June 12, 2022 by April Maccario

There’s something about funny people, they are easy to be around, easy to talk to… and just fun. Based on that alone, it makes sense that you would want to try to make people laugh once in a while. 

So, let’s look at things this way, you met someone and you are hoping to engage him in a conversation that isn’t monotonous.

The best thing to do is to spur some laughter, but what are the major funny questions to ask a guy to make him laugh? If you're naturally funny, this may not sound like a big deal, you probably ask guys questions all the time. But if you're one of the awkward ones like I am, you'll be needing some guidance. 

So if you want to ask questions to a guy and get the conversation flowing, without making him feel uncomfortable and keeping his rights reserved, here are 101 questions to ask.

101 Funny Questions To Make A Guy Laugh

101 funny questions to make a guy laugh
  1. Do you have a funny nickname?
  2. Have you had an embarrassing moment that you now consider funny?
  3. What is the weirdest thing you've seen?
  4. What is the strangest thing you have seen in someone else's house?
  5. What would be your first step as president?
  6. What is the funniest word you know?
  7. Have you ever been able to stop laughing in an inappropriate place?
  8. What is the funniest joke you know?
  9. What is the weirdest thing you've had in the fridge?
  10. What's the weirdest thing you've had in the car?
  11. What is the weirdest thing you've had in your room?
  12. If you had a magic lamp, what would your three wishes be?
  13. What is your worst guilty pleasure?
  14. What do you think is your funniest body part?
  15. What is the weirdest thing you've seen your pet do?
  16. What is the weirdest thing you've seen your parents do?
  17. What's the strangest thing you've ever eaten?
  18. Have you ever made a phone prank?
  19. Have you ever played a prank on a friend?
  20. What would you do if you won a million dollars or euros?
  21. What is the most surreal dream you've ever had?
  22. Do you have a word that makes you laugh uncontrollably?
  23. What gesture makes you laugh uncontrollably?
  24. Do you sing in the shower?
  25. Have you ever been caught singing when you thought no one was listening?
  26. Have you ever greeted the wrong person?
  27. Which celebrity would you resurrect?
  28. What is your perfect idea of a movie?
  29. What is your perfect idea of a TV series?
  30. What is your perfect idea of a novel?
  31. What is your favorite potato flavor?
  32. Which historical person do you want to talk to?
  33. What superpower do you want to have?
  34. What is it that others can't stand about you?
  35. What is it you can't stand about yourself?
  36. Do you like dressing up?
  37. If you had all the money in the world, how will you spend your time?
  38. What would you say to your boss if you won the lottery?
  39. What's your worst childhood prank?
  40. What alias will you use if you were a secret spy?
  41. Who would you hate to see without clothes?
  42. Which magazine do you want to be on the cover of?
  43. Who is the famous person you have met?
  44. What is your most absurd achievement?
  45. What animal would you like to be?
  46. Which animal best describes you?
  47. If you were an ad, what slogan will you use?
  48. If you were told that you can do anything without suffering the consequences, what would you do?
  49. How do you seduce someone of the opposite sex?
  50. ...And someone of the same sex?
and someone of the same sex
  1. You have five seconds to make a wish. Which would you choose?
  2. What is the curious fact that you find the funniest?
  3. If you had to start a dry, what would it be like?
  4. What has been your most surreal date?
  5. Have you ever been caught stealing?
  6. What would you do if you ran out of toilet paper in the bathroom?
  7. Where would you bury a treasure?
  8. Where would you bury someone you just killed?
  9. Have you ever counted your steps as you walk?
  10. Do you have any hobby when walking, like stepping on even tiles?
  11. What is your ideal profession?
  12. If you were a zombie, who will you eat first?
  13. Have you ever burned something in the oven?
  14. What is your favorite Instagram filter?
  15. If you were mistaken for an actor or actress, who do you want it to be?
  16. How will you react if you were attacked or attacked by a bear?
  17. If you woke up being the opposite sex, what would you do?
  18. Have you ever seen a UFO? If you ever saw a UFO, would you choose to follow?
  19. What is the craziest thing you've done for love?
  20. Have you ever listened to the horoscope?
  21. Are you able to move your nose or ears?
  22. Can you suck your elbow?
  23. Do you have any strange talents?
  24. What's the stupidest phrase you've uttered?
  25. If you were your own psychiatrist, what would you say to yourself?
  26. Can you stare at someone for a minute without laughing?
  27. If you could exchange your life with someone, who will it be?
  28. What song can't you bear but you know it by heart?
  29. What would you do if you met your own double?
  30. What is your favorite smell?
  31. If you were a ghost, how would you scare people?
  32. Which tv show seems stupid to you?
  33. The weirdest place you've relieved yourself?
  34. If someone played a nasty joke on you, how will you revenge?
  35. Which part of your body tickles you the most?
  36. What has been your funniest fall?
  37. What kind of people do you find more fun?
  38. Any insult that seems extremely funny to you?
  39. What is the strangest thing you have seen on the Internet?
  40. Do you have any strange superstitions?
  41. If you were an object, what would you be?
  42. If you were a color, what would you be?
  43. If you were a television show, what will you be?
  44. Has an almost miraculous chance happened to you?
  45. What is the strangest thing you have done being alone?
  46. How will you define the Internet in one word?
  47. What was your first impression of me?
  48.  Do you look behind me when I'm in front?
  49. Will you ever like to play roles in bed?
  50. Do you think you could handle all day in heels?
  51. If I say "sexy", what is the first thing you think?

Most Popular Fun Questions To Ask A Guy

most popular questions to ask a guy

Now let’s take a look at a few of the most popular funny questions to ask a guy, why they are commonly used and how they can get the conversation flowing;

1. What’s The Most Embarrassing Thing You’ve Done?

If the air is tense and you’re after funny questions to ask a guy, this one is bound to cut through it perfectly, even if he is not the kind of guy that will want to reveal embarrassing things about himself, it does not hurt to resort to questions such as this one. 

You see, as far as funny questions go, this is one of the most common and perhaps thoughtful. 

It does not simply give you both something to giggle about, it further reveals part of his character. During the course of your conversation, he won’t even know when he loosens up thanks to these funny questions. 

Even more, you’ll feel closer to him since you’ll both share a secret. All in all, this should probably be one of the first questions you should throw his way if you really want to get a sense of who he is and get the conversation flowing.

2. What Do You Consider To Be The Funniest Thing In The World?

If you really want to get him in stitches, this is one of the best funny questions to ask a guy. Altogether, knowing what he finds funny is a great way to lighten the mood. It also goes a long way if you want to get to know him. 

It’s an excellent question to ask guy, it’s very engaging and could equally contribute to setting the tone for your relationship. So, if you are looking for funny questions to ask, pick this one. Why? Well, if you enjoy the same things and share a sense of humor, you are bound to have an interesting time together.

3. Would You Rather Be Rich Or Happy (You Can’t Be Both)?

would you rather be rich or happy (you can't be both)

So, this may not necessarily be among the top funny questions to ask a guy. Nevertheless, it all depends on the way you ask a guy questions. This could be a really interesting one and it’ll equally reveal a lot about his personality. So, do not hesitate to chip this in during the course of your conversation. 

If he chooses riches, then you know he’s a bit cutthroat, yet ambitious. A lot of people would rather go for happiness because it breeds peace of mind. Altogether, consider this when you are looking for some fun questions to ask that special guy.

4. When Was The Last Time You Cried And What Did You Cry Over?

They’ll tell you it's weird for a man to cry, but there is no one that can say they haven’t cried once or a million times. So, if you are looking for funny questions to ask a guy, this is a go-to option. It has the right ‘fun questions to ask’ to ‘deep questions’ ratio. Even if he does not answer, it still reveals a whole lot about him. 

If he does answer, then you are in luck since you’ll get to see a softer side of him. This study here shows that men cry 5 to 17 times a year, so he possibly cannot claim that he’s never cried. Altogether, if you really want to know more about him, especially if the last thing he cried about was bizarre, then try it. 

If he’s the fun type, questions such as this will really make him laugh, so you can get to know him better. It's just one of those questions that will really drive it there.


What is a fun question to ask a guy?

There are tons of funny questions to ask as a conversation starter, or if you really want to get to know a guy. Before you pick one, make sure you have a sense of who this guy is. Have a nice talk and pull the question from his experiences. You could ask him questions about his quirks, his most embarrassing experience, and more stuff along that line. 

What flirty questions to ask a guy you like? 

On this front, things get interesting because there's so much to pull from, but again, it depends on his orientation and personality. Nevertheless, if you want to play safe when thinking of funny questions to ask a guy, it's always safe to go for things like, 'you look great, where do you work out?'. Or, you could take it a notch higher and ask a guy if he's ever gone skinny dipping. That will definitely lead you down a flirty road. 

What should you never ask a guy?

Now, there's a whole lot of content to draw from here, for the most part, it's a one size fits all situation. There are things every human would and should consider out of bounds. Don't ask a guy how many abortions his exes have had for him. Also, don't ask him how many girls he's slept with or how much money he makes. Anything along those lines and a lot more is more humiliating than humorous. 

What is it that makes him laugh?

Again, this is very relative and depends on his sense of humor altogether. If he has a dry sense of humor, he'll probably get more sarcastic and subtle jokes. On the other hand, someone with a wetter sense of humor will go nuts for just about anything. The trick here is to know your audience and you’ll be fine. That said, funny questions will definitely get the conversation flowing.

What is a tricky question?

A tricky question is exactly what it sounds like, it's puzzling, it's hard to understand, and will give people something to think about. Not only is it quite difficult to answer, but it equally has a very obvious answer. For instance, ‘How can you go eight days without sleep?’ The answer is, ‘By sleeping at night’.

In A Nutshell

Whether it's the first time you’ve met or you’ve been together for quite some time, if you want to know what are questions to ask a guy, funny questions always cut the tension. Just being able to lighten the mood can go a long way to set a good premise for the entire relationship. 

You see, having a sense of humor is a serious deal-breaker to get to know a guy. So, it’s not a bad idea to stock up on some of these funny questions to ask a guy, as mentioned earlier, not everyone has these lines rolling off their tongue, and so, we hope this inspired some great funny questions.

If there are any funny questions to ask a guy which was left out, I’m welcome to all sorts of input. Even more, share this with someone who needs a nudge in the right direction. 

Frustrated that he doesn't pay you as much attention as he used to?
This is one of the most common issues our female readers face.

It makes you wonder whether he actually likes you or not.

Take this free quiz to see if he actually likes you!

Do you hate it how everything seems to always revolve round him while you just seem to be an afterthought sometimes?
We hear this all the time from women that contact us asking for help with their relationship.

It almost makes you wonder whether he actually likes you or whether he's just stringing you along.

Why don't you take this quick free quiz to see if he actually likes you!

April Maccario
I'm a huge nerd when it comes to understanding how relationships between men and women work, and what drives a certain behavior. I spend much of my time getting into the nitty-gritty and try to share my findings on this site with the hope of making life a little easier for women that are struggling in their relationships or love life.

Leave a Reply

Your email address will not be published.