27 Happy, Fun Questions to Ask a Guy to Make Him Laugh & Smile Around You

Looking for fun questions to ask a guy to make him laugh? Look no further! This list will make him think you’re the funniest person to be around.

Guys like fun. They like girls who are laid back and know how to have a good time. So that means getting their attention is easier if you show them a more exciting side of you. In order to do this, you’ll want to know some fun questions to ask a guy to make him laugh.

These questions will get you there, whether you want to make him laugh, smile, or just think you are fun.

The best way to show him you’re a good time is through conversation. Talking, texting, or sitting at a bar, making him laugh with our unique and fun questions will help him see the best side of you. [Read: Ways to make a guy laugh]

What does being fun mean?

Society has given many women the wrong impression. Being fun does not have to mean being easy or sexual. Sure, if you want to have sex, do it safely—more power to you.

But sex and fun are not mutually exclusive. Guys want a girl who is fun with her words, mannerisms, and sense of humor, not just her body *at least any decent guys*.

There is nothing wrong with having fun sexually, but having fun questions to ask a guy to make him laugh is key if you are interested in getting his attention in another way.

Talk to him. Get to know him. Let him get to know you. Asking fun questions is the perfect way to start a potentially amazing relationship. [Read: 18 things you do that make guys think you’re easy]

Fun questions to ask a guy to make him laugh

When you’re just getting to know a guy you like, asking the right questions can mean the difference between him seeing you as fun and exciting and not being interested.

Don’t risk seeming boring. Show him your fun side and gain his affection with these fun questions to ask a guy.

1. What’s the most embarrassing thing you’ve ever done?

While he might not want to divulge the most embarrassing thing he’s ever done, it will be funny. Plus, if he’s game, it shows he can be humble and fun too. If he won’t share, he may take himself too seriously.

But remember, having fun questions to ask a guy isn’t just for him but for you, too, so get your most embarrassing story ready. [Read: 15 painfully embarrassing things that happen during sex]

2. When was the last time you made a fool of yourself?

We’ve all done it. It’s not quite the same thing as embarrassing yourself, either. It’s more of a time when you just did something silly or stupid without thinking. This question could lead to some laughs and a great conversation.

3. What’s the funniest thing in the world to you?

One way to get someone laughing is to talk about something they find funny.

Not only will you learn more about him this way, but you’ll also determine if you two have something in common. If you both have the same sense of humor, it bodes well for a future romance for you.

4. If coffee wasn’t legal, what would it be called on the black market?

This is just a cute and fun question to get his mind turning. You can talk about what it would cost if people would make up different variations and more. It’s a great conversation starter, too. [Read: 20 intriguing conversation starters for a casual coffee date]

5. If your life was a show, what would the theme song be?

Not only will he have fun with this, but you’ll also get to know a bit more about him. His taste in music will become evident, but so will the events in his life. It’s like a sneaky, fun question to ask a guy to not only make him laugh but also learn so much more about him.

6. What’s a movie you’re embarrassed to admit you love?

This will show you where his true tastes lie. Many guys say they like action movies or stuff that’s more mainstream. But every guy has a guilty pleasure that isn’t exactly “manly.”

It’s not only fun to find out what his guilty pleasure film is, but it also shows you a different side of him that others don’t often get to see.

7. If you were given $1,000,000 tomorrow, what would you do with it?

This is a super fun question because there are so many possibilities. Becoming $1,000,000 richer overnight is a huge change. You’ll find out how he would spend the money, whether that be responsibly by saving it or recklessly by splurging it on expensive cars and massive houses. [Read: 30 would you rather questions to leave you thinking]

8. What’s the first thing you’d do if you woke up as a girl?

We all know what his answer will be, but it will be funny to make him say it out loud. Just be prepared for him to ask the same of you if you woke up as a guy – and be honest! You’ll both be laughing in no time.

9. What’s the grossest thing you did as a kid?

We’ve all done icky things as kids. From putting bugs in our pockets to playing with the dogs… excrement… we were all disgusting children at one point.

Ask him what he did and see if it’s really that gross. Just be prepared to see him in a new light!

10. If your life was a reality show, what would you call it?

This is another way to find out more about his life while keeping the mood light and playful. By the name that he comes up with, you’ll be able to find out a lot about him and what his life is like right now.

This is a fun question to ask a guy to make him laugh because you’ll have to answer it too. Don’t be afraid to get wacky with your answer! [Read: 30 deep questions to ask someone and get to know them better]

11. If the last thing you ate is the only thing you can eat for the rest of your life, how soon will you die?

Did he eat a full meal of nutritious foods? Then he’d be safe. If the last thing he ate was a chocolate bar… he might die a bit sooner.

This is just a goofy question that can lead to a longer conversation about food. And who doesn’t love talking about food?

12. If you could only ever be one, would you rather be smart or happy? Why?

This will tell you a lot about him. Most people would choose to be happy because who would want to go through life not feeling that way? But you never know. Some people may choose to be smart. Find out where his thoughts lie.

This could reveal if he’s the type of person to prioritize happiness and personal achievement or a workaholic who puts their career or financial success above all else.

13. If you had the chance to live on Mars but could never come back, would you do it?

This is a real possibility for some people. Travel to Mars will someday be available, maybe even sooner than we realize. But it’s very likely that if you go to Mars, you’ll never come back to this planet. See what his thoughts are and just how adventurous he can be.

Also, ask him what he thinks life on Mars, or in space in general, is like. Does he believe in aliens? What does he think still has to be discovered in space?

This is a fun question to ask a guy to really get to know each other better. [Read: 36 racy and funny questions for flirty guys and girls]

14. What’s the last thing you cried over?

You may not get an honest answer out of this, but this question digs a little bit deeper than the rest on this list.

It may not be super fun, but it is a great question to ask a guy. And, who knows? It still could be fun because some guys cry over silly things. And he might just tell you what he cried over as a kid, and usually, those things are pretty silly.

Although, if you’re only intention is to make a guy laugh and show him your fun side, use this question with caution. There is the chance of royally screwing up the mood with this one.

15. What’s your dream job – if you could do absolutely anything?

Imagining a dream life is always fun. Ask him what he’d do if he could do anything. You’d be surprised what he might choose. Then you can talk more about it and why he’s not making that dream a reality. It’s a fun question to ask a guy that can lead to a much better and even deeper conversation.

16. What were you like as a teenager?

This is always a fun question. Whether he enjoyed his teen years or not, looking back is always a blast. He’ll surely share something embarrassing. [Read: Fun and cute questions to ask your boyfriend]

17. What is your guilty pleasure?

Does he secretly binge The Bachelor? Maybe he indulges in some weird food combos? Find out what he enjoys on the DL. The fact that he is admitting it to you will bring you closer.

18. What are your favorite memes right now?

As much as we may not want to admit it, memes are a huge part of today’s culture. If he is anywhere on the internet, he will have a favorite meme that he has screenshotted or shared with friends. Find out his favorites and share your own.

19. What makes you feel old?

Whether he is in his early twenties, late thirties, or any other age, there are always things that make him feel old. This is a fun question to ask a guy to make him laugh so you can bond over similar ages or joke over being far apart in age. [Read: Dating age rules]

20. What are you weirdly afraid of?

Does he hate snakes, spiders, or the dark? We all have some bizarre fears. Share yours and discuss them. This is hilarious and can turn into a deeper conversation, too.

21. What was your first impression of me?

This is more of a fun question to ask a guy for you than him, but if he asks you the same question back, it will surely be fun. Find out if he thought you were too much at first or quiet when you’re actually super outgoing. [Read: 30 signs he likes you]

22. What is the most fun you’ve ever had?

Will he talk about something from his childhood or something he did with his buddies last year? This will show you how he likes to spend his free time and if you have similar vibes.

23. Which celebrity do you look up to the most?

This question can be deep, but it will surely be fun. Does he look up to someone like The Rock, Robin Williams, or someone totally different, like a politician? This can tell you a lot about him in a super fun way. [Read: Love advice from famous Hollywood couples]

24. Show me the funniest picture you have saved on your phone.

Okay, so this isn’t exactly a question to ask a guy, but it is close. This is sure to inspire some laughs from both sides.

You can both scroll through your albums and show each other funny photos of your dogs, embarrassing baby photos, and more.

25. If you could talk to animals, what is the first thing you would ask?

If he has a pet, this will be so interesting. Does he want his pet to know he loves him or ask what his favorite food is? If not, what animals would he talk to?

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

Hopefully, this is more fun than it is sad. And it should be. Usually, the worst dates end up being pretty funny in hindsight. And it will show him how much fun he’s having with you in comparison. [Read: Signs of a bad first date]

27. What is something you want to know about me?

Now it is his turn. Turn the tables on him and make him put in the effort. He should think of some fun questions to ask you too. After all, it’s not your responsibility to carry this date.

[Read: 20 good questions to ask a guy to find out who he really is]

Knowing fun questions to ask a guy can save a conversation and show him you’re a good time. Once you’re in, you can start laying down the groundwork to win his heart.