Funny Questions to Ask a Guy: 22 Questions To Get Him Laughing

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If there’s one surefire way to a man’s heart, it’s through laughter. Whether you’re having your very first conversation with a man you find attractive, you’re on a first date, or you’re on a 20th date, it never hurts to have a bank of funny questions to ask a guy.

Every Man Likes a Woman That Can Make Him Laugh

laughing couple

Getting him to laugh practically guarantees a second date!

So you know the whole scientific data thing about how men are attracted to women who would make good babies, even if they don’t want kids, right? Well, a similar attraction happens when a woman makes a man laugh.

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Research shows that couples who laugh a lot — and at the same sorts of things — tend to have more satisfying relationships. So getting a man to laugh now could build the foundation for a healthy (and hilarious) relationship in the future.

A lot rides on that first meet or first date. You’re unfortunately being judged every second. This man is wondering if he likes you enough to see you again and if you have anything in common. You’re probably going to be nervous, which makes it all too easy to be overly serious. That’s not really the impression you want to give a man.

On the other hand, if you can make light of the situation (Look! My palms are sweating. Do you do that to all girls?) you’ll break the ice and make him laugh. That’s a fantastic first impression guaranteed to get you another date.

Funny Questions to Ask a Guy

Now I want to break down the funny questions to ask a guy into three categories, each with its own purpose.

But first, a few tips on asking the funny questions. Remember that it’s not just the questions that will get a laugh. Your delivery is key to your success. You can ask the question with a totally straight face:

So, can I ask you something personal? I mean like really, really personal?

At this point, he’s going to start sweating a little because he’s not sure he wants to get so personal on a first date. Then you drop the absurd question. He will be speechless…before he starts cracking up.

Or you can make a silly face or cock your eyebrow to give him a heads-up that you’re about to get a little goofy on him.

Whatever approach you take, make sure a smile follows. It is, after all, your most attractive feature.

Random Ice-Breaker Questions

goofy woman

These icebreakers are designed to get you both to loosen up on a date.

The first funny questions to ask a guy we’ll cover are hilarious ice-breaker questions to get the conversation started. These are useful if you’re nervous (or he is) and don’t know what to bring up, or if you’ve hit a lull in the conversation.

They’re also good if you’re texting a guy you met through online dating. The same old what do you do for a living questions get mighty old, and some guys decide whether or not to ask a woman out based on whether she asks the same questions as every other woman or not. You can stand out by asking the unexpected.

  • If you were invisible for a day, what would you do?
  • What’s the sexiest animal on the planet?
  • When was the last time you peed in the pool?
  • What about the sink?
  • Why do men have nipples?

Silly Questions to Get to Know Him

funny questions to ask a guy

These funny questions to ask a guy will get him to open up.

These funny questions to ask a guy are actually really useful. You want to know about his background, his family, his job, his personality, but you want to avoid asking him the same old questions every other woman he’s ever dated has asked. So you tackle topics in an innovative way.

These, too, are useful for guys you text via a dating app, particularly as that first question to get the chat going. Men, just like women, won’t respond if the opener is particularly lame or uncreative. That’s why you’ve got to think outside the box when it comes to getting him to respond to your first message (particularly on dating apps where the woman has to make the first move, like Bumble).

You can ask zany questions that get him to talk about his childhood:

  • Who was your celebrity crush as a teen?
  • What was the first concert you ever went to?
  • What is the weirdest nickname people call you?
  • If you have siblings, who was the bully growing up?

You can also ask questions that tell you a little about his personality and who he is outside the perfect persona he’s put on for this date.

  • Have you ever stolen anything?
  • What’s your spirit animal? Why?
  • If you saw a pile of cash on the sidewalk and no one was around, what would you do?
  • What is the most embarrassing thing someone has caught you doing?
  • What TV show character is most like you?
  • If a movie was made about your life, what would the title be?

You can even get him to talk about his job:

  • What’s the stupidest thing you ever did at work?
  • How would you get yourself fired if you could?
  • What would your coworkers put on your dating profile about you?

Flirty Questions to Ask Him


These silly questions let him know you’re interested.

So that you avoid giving him the third degree on your first date, mix some of the funny questions to ask a guy with some of these more flirty questions that show your interest. You don’t want him to think you’re just here to grill him! Let him know through your silly questions that things are going well on the date.

  • What is the cheesiest pickup line you’ve ever tried to use on a girl? Did it work?
  • What do you like for breakfast? Just asking!
  • Are you allergic to lipstick?
  • If you had to choose between winning $1,000 right now or finishing this date, which would you choose?

Why It’s Important to Show a Good Sense of Humor Around a Guy

There’s a reason why so many men have “must have a sense of humor” on their dating profiles. Being witty is hella attractive!

But it goes deeper than that. When you demonstrate that you have a sense of humor, you’re subtly communicating that you’re probably a go-with-the-flow type of gal. A woman who can laugh at herself is one who probably doesn’t stress too much (even if you do, you at least give the impression that you don’t!).

If you can make fun of yourself, you show that you don’t take things too seriously. Remember the kid in junior high who cried every single time someone played a practical joke on him? Now, do you also remember the kid who would laugh when someone made fun of her or even would make fun of herself? Who do you think is more fun to hang out with as an adult?

In a scientific study, researchers found that participants who could laugh at themselves were more authentic…and even healthier.

Ursula Beermann, Senior Lecturer at the Institute of Psychology at the University of Innsbruck, says not taking yourself too seriously shows that you “acknowledge that you are not the center of the universe.”

That’s a pretty cool woman, in my book: one who knows that it’s okay to be teased and to do the teasing from time to time. It’s all in fun, right?

A woman who laughs a lot and who exhibits a solid sense of humor is one who’s fun to be around. Men like to date fun women. Sure, eventually he’ll get to know your sensitive side if you end up in a relationship with him, but you’ve got to put your best foot forward early on so that he becomes invested enough to want to get to know you more.


smiling lady

Practice makes perfect! Try out your funny questions until you’re confident asking them.

As you start to use these funny questions to ask a guy, pay attention to results. Just like a comedian, you’ll have to fine-tune your performance. You might find that one question gets strange looks from your audience (your date). Maybe take that off the list.

Be open to where the question takes you. For example: if you ask when was the last time you peed in the pool and it leads to him telling a story about being a kid in Hawaii, drop the funny questions and just have a conversation. Your date should in no way be made up of only these funny questions to ask a guy!

They’re meant more as punctuation in the conversation. If neither of you knows what to say, pull one out of that drawer in your head.

Test them out via text or dating app and see which one gets the most responses.

If you’re nervous about asking the questions, try them out in front of the mirror, also practicing either your straight face or your ridiculous look. Use your friends as guinea pigs and get their input on which questions are the funniest.

With a little practice, you’ll be able to come up with more funny questions to ask a guy on the fly!

Do you have any funny questions to ask a guy that you can share with other readers? Share them in the comments below.

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6 years ago

Hell no!!! not confident with a man i like( Alas… when it comes to work, my opinion or stuff that i do – i’m confident and sometimes even self-assured. but when it comes to an attractive man – i’m just as timid as a pigeon. But when i watch your videos, Adam, i start recognize my mistakes and work on myself , train myself by meeting lots of men and be myself no matter what (no make-up, dirty hair, lousy clothes:) And funny how: men DO stay interested when i am as i am! still, there is a long road… Read more »

6 years ago

Great video! Thanks for ALL of the awesome dating advice that you give!!

Sheila Aleck
6 years ago

Really needed this thanks heaps

5 years ago

These were really great questions to read. I really enjoyed your post. Please keep it further updated with time as I have a habit to save the good links like this and visit them regularly to get more fun.

4 years ago

I really don’t know the definition of sexy. People sometimes tease women by throwing the word “sexy” but this does not make sense to me. Are those women really sexy that’s why people called them sexy or anything else? Really I don’t know. But I love your YT videos, those are really sexy.

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