30 Funny Questions to Ask a Guy to Make Him Laugh

Asking a guy funny questions is one of the many ways a woman can keep the conversation going. When everybody is laughing, it is usually a good sign that things are working out for the best. It would certainly be boring if either the man or the woman kept asking serious or personal questions on a night out or over text.

However, coming up with funny questions is not as easy as it may sound. Guys may generally be more likely to have a hang of being funny because they are used to controlling and setting the tone of a conversation with a lady. Every woman wants to be with a guy that can make her laugh, so this is something most men try to work on early in life when they start making advances on women.

Because women don’t have the burden of being the entertaining ones, they most likely would have a hard time coming up with funny questions that can make a guy laugh unless it comes naturally to them. Below are a few questions that a lady can use to lighten up her conversation with a guy.

Funny Date Questions to Ask a Guy

These questions can be asked to a guy when out on a date. They are generally questions that can lead to the guy sharing a funny story or showcasing his sense of humor with his responses.

1. If we were the only two people remaining on earth, what is the first thing you would do?

This question is not just funny but also tricky. It would not only fulfill your intention of making the guy laugh but would also reveal a few other things about him by exploring his idea of an apocalyptic world. Some would also say that if he jumps to talk about procreating to extend the existence of mankind on earth, it tells you where his mind and intentions are with you. Whatever the case is, it is a beautiful way to break the ice on a night out.

2. What was the worst date you’ve ever been on?

It hurts when you go on a date, and it does not pan out the way you planned. Like women, guys also feel bad when dates go sideways. Asking him this question that allows him to share a bad experience goes a long way in getting you guys to bond. One or two stories that he shares would also be funny.

3. What topic can you never get tired of talking about?

This question will lighten the mood because it allows the guy to talk about a topic that particularly interests him. It could be sports, science, cryptocurrency, etc. Hopefully, it is not a topic that bores you or something you have no clue about. But which way it goes, you stand to learn a thing or two about that topic while the guy is given a chance to be at his absolute best and impress you with his knowledge.

4. What’s your worst experience in the kitchen?

Even though there are more male professional chefs than female chefs in the world, it is widely believed that the average guy does not know their way around the kitchen. If the guy is one that can whip up a decent meal, this question might turn out to not be funny at all. However, if he is one of the many that have almost burned down the house while trying to cook something, brace yourself for a funny response.

5. If you saw me in handcuffs, what crime would you think I committed?

This is undoubtedly a funny question that would make the mind wander. The guy has a chance to come up with a creative crime that you may have done. If he is smart enough, he could sneak in a compliment like, “you were arrested for being too hot.”

6. If you started a cult, what kind would it be?

This is another question that gives him a chance to compliment you if he knows what he is doing. He could respond by saying, “a cult that worships you.”

7. Would you spit into the meal of a rude customer if you were a waiter?

Many people have a hard time forgiving and would not be able to let go of a transgression without trying to get back at them. This is a funny question to ask a guy that helps you gauge his level of pettiness.

8. Do you like a woman who wears make-up?

This is probably a weird question to ask a guy when you are already out on a date with him because you might already have make-up on. However, it would not hurt to know how he truly feels about women wearing makeup. While it may be something that every woman does today, it is not something that every man likes seeing on their woman.

9. If you could be either a ghost or an invisible person for a day, what are the things you would do?

Another one of those questions would make the mind wander. People have a lot of things that they would do if no one were looking. Find out what the guy says he would do; we bet that it would be something hilarious like taking money out of a bank vault in broad daylight or messing with random people by moving things around them.

10. What do you see yourself doing in about one hour?

The date is probably coming to an end, and you are looking to take things a step further. Asking him what he would be doing in an hour is a funny and clever way of finding out if he wouldn’t mind spending more time with you because he enjoys your company or can’t wait to move on to other things.

Funny Questions to Ask a Guy Over Text

These types of funny questions to ask a guy do not require a long answer since it is over a text. There is, however, room for more to follow since they are open-ended questions.

11. What is your favorite comedy movie?

Since you are trying to send a text that has a funny question, you might as well start by asking him about his favorite comedy movie. This throws a light on his sense of humor and what exactly gets him going.

12. What weird smell do you find appealing?

Some people can’t stand the gasoline smell, while others find it fascinating. Some people also enjoy the smell of their farts, while others see it as disgusting. Whatever answer they have must be amusing to find out.

13. What are the top three things that would make you laugh the hardest?

Since you ask for things that make him laugh the hardest, expect the unexpected. Men have a different sense of humor so remember not to judge them for their responses because if he is sincere with the things that make him laugh hard, it could be something that might gross you out.

14. How many dating apps have you ever used?

Almost all single men and women use dating apps. When they cannot find a suitable partner on one, they download another to try their luck. The cycle continues until they have a boatload of dating apps on their phone. They are probably embarrassed about some because they could be designed specifically for swingers, gay people, people of faith, etc. Again, if they are being truthful about it, both the question and whatever response you get is sure to be hilarious.

15. What is the most sensitive part of your body?

While this question may be borderline sexual, it could also be a very funny one depending on where the guy identifies as his most sensitive part. It is hilarious hearing a guy say his earlobes or belly button are his most sensitive parts. Ask a follow-up question on how he found out they were his most sensitive parts and sit back to hear another hilarious story.

16. What is the stupidest thing you have ever done?

This is another one of those questions that would lead to a fantastic but amusing story. No one can deny that they have never done any stupid thing that they were not proud of.

17. What are you like when you are drunk?

This is a great follow-up funny question to ask a guy via text after asking him about the stupidest thing he has ever done. When drunk, people tend to do silly things that would entertain anybody watching it from afar. They are most times very funny. However, on other occasions, they could get violent and annoying.

18. Do you have any funny nicknames from your childhood?

Most kids have that one nickname that they never want to hear. They also did everything possible to let go of it, so it would take something special to get him to tell you what it is.

19. What is the worst pickup line you have ever used?

There is a very thin line between a pickup line being very good or very bad. Find out which one he used in the past did not get the reaction he desired. The circumstances surrounding the whole ordeal will undoubtedly be hilarious.

20. On a scale of 1 to 10, how well do you sound when singing in the bathroom?

Every guy who takes time to sing in the bathroom believes they are either Lionel Richie, Luther Vandross, or Usher. Find out where he would rank himself and see how confident he is about his abilities.

Questions to Ask a Guy for Fun

These types of funny questions to ask a guy are ones that can be used at random. There is no time and place for them. They are only designed to explore his sense of humor.

21. What song comes into your mind when you see two people about to fight or when you are about to get into a fight?

Most fighting scenes in movies have a song or jingle that comes on as soon as people are about to get physical with one another. Subconsciously, this also happens to people in real life. Asking a guy such a fun question would reveal more about their sense of humor and the type of songs they might be interested in.

22. If either you or your family had an insignia (badge), what exactly would it be?

In the past, each notable family had an insignia that was used to distinguish themselves from another. This badge or emblem could be an animal like a lion, bear, eagle, or a weapon like swords, guns, etc. Others even used roses or other crops that were unique to their lands. Asking such a fun question can paint a picture of what the guy thinks of himself and where he comes from.

23. What name would you go for if you decided to become a Disc Jockey?

DJs have the most ridiculous names – DJ All Night Long, DJ Big Willie, DJ Pants Down, etc. Find out how creative he is with a possible DJ name. Depending on how mischievous he intends to be, there would undoubtedly be laughter.

24. If given a chance to have a camera anywhere in the world, where would you put it?

Yes, he probably thought about putting the camera in your bathroom or that of the woman of his wildest dreams. Just look at his face. The smile and laugh are a dead giveaway.

25. What popular catchphrase from a TV show or movie do you often use?

“Hasta La Vista,” “Yabba dabba doo,” “Houston, we have a problem,” etc., are some of the many catchphrases from TV that have become a favorite of people to use in their day to day activities. This is a fun question to ask a guy because it can take him down memory lane, which would be fun for you to hear.

26. What is the funniest thing that happened to you as a child?

Did he get slapped by a girl he was trying to kiss? Did he mistakenly shit his pants in class while trying to fart? We have all been in situations that we can call funny today but did not feel anything like it when it initially occurred.

27. Which movie do you feel needs a sequel?

There are countless movies that fans believe ended badly. It could either be because the protagonist died or didn’t get justice at the end. Whatever the case is, hearing their opinion on why the movie needs a sequel could crack your ribs.

28. What would you say to the leader of your country if you randomly ran into them?

Politics is usually a sour subject to bring up because it can quickly dampen the mood, especially when you have different political affiliations and ideologies with the person. However, if you can look past political beliefs, a hilarious answer is certainly on cue with this question because they would either say or do something outrageous.

29. What is the one thing you are terrible at and hate to admit?

Most times, the thing that we are terrible at but hate to admit is something that most people can do. This, therefore, makes it quite funny.

30. Have you ever been accidentally caught naked?

We all have experienced times when either a friend or a relative barged into our room or bathroom unannounced, thus seeing us all in our glory. This time could either be one of the most embarrassing or funniest moments ever, but it would be a fun story to share. Find out which one it is.

Chizzy Onukogu
Chizzy Onukogu
Chizitere is a writer and editor with over five years of experience in producing articles on various subjects. My writings have been published on multiple websites and publications


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