99 Weird, Funny Questions to Ask a Guy to Show Off Your Fun & Playful Side

Looking for funny 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 funny 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.

[Read: Ways to make a guy laugh without dumbing yourself down]

What Do Guys Like Fun Girls?

Well, the answer is pretty simple—because they’re fun to be around! If you’re dating someone, with long-term goals in mind or for just a little fling, you’re only going to have a good time with someone that you can have fun with.

Dating someone who is serious all the time, pessimistic, and incessantly negative, their bad mood will rub off on you. This isn’t just hearsay, this is science! Psychologists often refer to emotional contagion, the theory that we automatically adapt and share emotions with those around us.

So, when we date fun people, we have fun! And when we date rude, arrogant, or negative people, our world lenses shift to be like theirs. [Read: Negative Nancy – what makes one, 18 traits, and ways to deal with their attitude]

The Best 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 funny 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, the story he does choose to tell you will still 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 funny 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: 80 very good conversation starters that’ll make anyone love talking to you!]

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: 40 very deep questions to ask someone before you get close to them]

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: 100 juicy, sexual questions to ask friends and have a fun, naughty time]

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 your 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 might be surprised with 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: 94 super cute questions to ask your boyfriend for a fun, happy conversation]

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 rule – what’s an acceptable age gap for a couple?]

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: Does he like me? 101 subtle signs and body language clues guys can’t hide]

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: 59 relationship lessons and honest love advice only experience can teach you]

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: 51 warning signs of a bad first date and big red flags in the first few dates]

27. What’s the grossest food you’ve ever eaten?

We all have that one food that stands out in our minds. And usually, it comes with a pretty awful, but funny story.

You can tell them about yours and get a really goofy conversation going. It’s definitely not a question he’d expect from you. [Read: Non-nom no-nos – 17 foods to avoid before having sex]

28. If you could be an apple or a banana, which would you choose?

This might be an odd question but it’s also quite important. Plus, it’s a bit goofy and you’ll be able to show your more creative side. Tell him what you’d choose and allow him to pick one for himself. Don’t let him avoid answering!

29. Would you rather eat only chocolate every day for the rest of your life or only potato chips?

This is not only a very cute and silly question, but it’s also one that’ll help you get to know him a little more. If he chooses chocolate, he’s clearly a sweets guy. If he likes chips, he must prefer saltier snacks. [Read: Aphrodisiacs and food hell – a lover’s guide to eating well]

30. Have you ever done anything embarrassing on purpose?

Some people like to do embarrassing things just for the fun of it. Is he one of them? Find out with this funny question to ask a guy. It’s not something people just go around asking so hearing it from you will definitely get his attention.

31. When did the phrase, “looks can be deceiving” actually happen to you?

This is a very odd question you almost never hear people asking. Make him tell you about a time when something wasn’t what it seemed. It’ll get an interesting conversation brewing and it’ll show him your silly side.

32. What would you do if I pretended to trip and injure myself right here?

Now, don’t actually injure yourself, but ask this question. It’ll make him scrunch his nose a little bit and be a bit more curious about you.

Plus, it’ll be fun for him to picture the scenario even if you don’t go through with it. [Read: 15 fun, weird, and intimate things to do as a couple]

33. What was your favorite family activity when you were little?

Not many of us think about what we loved to do most with our families when we were little. It could be something really ridiculous and goofy. He’ll be intrigued by your answer to this question, too.

34. What was your favorite insult as a child?

How often do you think about the insults you used to use? We all had crazy, weird things we used to call people when we got angry. Figure out his and then share yours.

We’re sure you’ll both end up laughing at your less-than-intimidating insults. [Read: 60 creative insults to taunt someone and leave everyone around laughing]

35. If I was a guy do you think we’d be friends?

Firstly, he’ll be intrigued simply because most girls don’t want the guys they’re into picturing them as a guy.

Secondly, it’s a good question to ask to see if he likes you for your personality. It’ll make him laugh, that’s for sure!

36. What movie trope irritates you the most?

There are tons out there. Damsel-in-distress saved by the knight-in-shining-armor, enemies-to-lovers, the list goes on and on.

This isn’t a question a lot of people ask so he’ll love that you do ask it. Plus, you’ll get to know him a little bit better. Just make sure to offer up your most hated trope first.

37. What movie quote do you use the most?

We all have that one movie we quote all the time. The weirdest part is that most people have no idea what we’re talking about when we use it. Share yours and see if he can guess it and vice versa. [Read: 69 best and most romantic movies that are a must-watch in 2023]

38. What’s your fast food horror story?

Plastic in a burger? Chicken nuggets that came in an off-putting color? Glass instead of salt on their fries?

We all have a fast food horror story that is hilarious to look back on. And we also know of someone with an even worse horror story, and sharing those can be even more hilarious.

If you really want to take the joke further, you can plan a surprise date to the fast food restaurant that traumatized him… And then take him to a nice restaurant to make it up to him!

39. What game do you dominate in?

Even those who aren’t the most competitive have that one game that they will absolutely annihilate everyone in.

Ask a guy what game he absolutely smashes in, and watch his face light up with passion as he talks about his favorite game.

And then, play it with him! See just how tough he really is! [Read: 15 fun relationship games for couples to feel more loved, connected, and happy]

40. What scene from a movie scarred you for life?

What scene from a film did he watch as a child that gave him nightmares for a week? When you ask him this funny question, you’ll not only bring up some childhood trauma in a hilarious way, but you also might uncover a secret fear of his.

With this question, you’ll have fun and get to know him in a real way.

41. What’s the most important file on your computer?

While this might be quite a weird question to ask a guy *because whoever thinks to ask about the files on someone’s computer?*, this might lead to some quite insightful answers.

Maybe he has a screenplay that he’s been working on for years that he’s passionate about. Or maybe his most treasured files are pictures from a family holiday.

You’ll take him back by asking this question, that’s for sure, but you’re bound to find out so much about him. [Read: 60 deep, fun questions to get to know someone romantically as a match]

42. What’s your hometown known for?

No matter how long it’s been since he’s stepped foot on home ground, his hometown still has a huge influence over who he is. So, find out who he is by asking him what his hometown is known for!

Is it the sports team *or its crazy mascot*, its beautiful scenic nature walks, or for selling the best hot dogs?

43. What is the future of dating?

In 50 years’ time will everyone say that they met their spouse on a dating website? Will it be common to marry a long-distance partner that you’ve never actually met before?

Will AI take over and use its advanced knowledge to perfectly pair us up with our other halves?

What does he think the future landscape of dating looks like? It’ll be fun to discuss all sorts of wacky and weird scenarios for what futuristic dating will look like. [Read: Meaning of dating – how it works, types, 42 signs, and ways to date someone right]

44. What, besides wealth, do you never have enough of?

Love? Power? Material possessions?

There are plenty of answers that your guy can come up with, and each one will reveal something entirely different about his personality. So, ask him what he thinks is the most important in the world, and see what you can learn about him!

45. What’s something that you’ve done that you would never recommend someone else to do?

We’ve all been young once, and we’ve all done stupid things. Have a laugh together and ask what stupid things he’s done!

Maybe he’ll tell you to never try dipping a mint in ketchup, or that rollerblading after having a few drinks is a bad, bad idea. By whipping out this weird question to ask a guy, you might just learn a useful life tip!

46. What’s the longest period of time you’ve been awake for?

Again, this isn’t something that people really know about their loved ones. That’s what makes this the perfect funny question to ask a guy to prove how unique you are!

Don’t forget to ask him why he stayed awake for so long as well. Was he a hard-working student? Is he a hard-core party animal who doesn’t shy away from a weekend bender? Or does he just get a little bit too distracted while playing video games? You could learn a lot about him. [Read: 34 secrets to get a man to open up, communicate, and understand you better]

47. What would be the most spectacular funeral you could imagine?

Funerals are seen as very sad events. And yes, saying goodbye to a loved one is a sad occasion. But, with a slight mindset change, funerals can actually be a great time to celebrate a wonderful life well lived.

So, set yourselves the task to plan the most spectacular celebration of a life that you can. How can you plan a fantastic funeral to lift the attendant’s spirits? [Read: YOLO – what it means and 23 secrets to live life like you only live once]

48. How often do you go on autopilot?

When we get into a routine, our brains turn off and our bodies just go on autopilot. And then, your brain might suddenly turn back on and you realize that you’re halfway through your walk to work.

How often does your guy go on autopilot mode? Does he often go about his day while mentally away with the fairies, or is he very grounded in reality?

49. What’s one fact that you wish you had never learned?

Did you know that dolphins aren’t actually as cute and sweet as they appear? Or that your nose is always in your line of sight but your brain just ignores it?

Let’s face it, we all know more than we really need to. And that’s usually thanks to either the internet or that one friend we all have who loves to torture us with useless or disturbing facts. So, ask him something that he wishes he never learned.

50. What board game can you not play civilly?

Above, we gave you an idea to learn what his favorite game is so that you can play together. But, while we’re on the topic, you might want to learn what game you should never, ever play together.

There are games that we’re good at, and then there are games that we’re passionate about. When we’re passionate about something, we can get very heated. Arguments can break out and loved ones can fall out, all over Monopoly pieces!

To avoid that happening to you, find out what board game never fails to turn him into a passionate ball of flame. [Read: 19 foreplay sex games for couples to get naughty and horny in minutes]

51. What would you do if you woke up tomorrow and it was 13 years in the past but you still had your current memories?

Hindsight is always 20/20, so what would happen if we could live our lives with the knowledge of hindsight?

Would he prevent something he regrets from ever happening? Or, knowing that the consequences wouldn’t be that severe, would he let loose and rebel?

It’s always fun to think about what we would do differently with the knowledge we have now.

52. What is the most useful life lesson your parent/s taught you?

“If you think that this problem won’t matter in five years, then you shouldn’t let it get to you now.” “If you don’t have anything nice to say, don’t say anything at all.” “Lefty loosey, righty tighty.”

Our parents impart so many lessons onto us as we grow up, but there are always a few that really stand out from the rest, even well into our adulthood. So, what life lesson stands out the most to him? And why does it? [Read: 36 life lessons to instantly transform your life and draw in happiness]

53. What piece of tech do you want to see invented in your lifetime?

Technology has advanced exponentially in recent years, so who’s to say what advancements we might see in our lifetime? While no one can say for sure what might be invented, it sure is fun to let your imagination go wild.

You could take turns bouncing ideas for revolutionary tech off each other well into the night.

54. What is the most boring activity?

Some things aren’t for everyone. So, what is one activity that he would never be caught dead doing? Hopefully, it’s not something that you love doing.

55. What part of your body would you replace with an improved mechanical version?

This is one of those funny questions to ask a guy that should get an equally fun and weird answer!

Would he want to replace a body part with an improved mechanical version for convenience or for improvement?

Maybe he’d replace his legs so that he never has to feel the pain of leg day again, or maybe he’d replace his arms to have super-human strength?

56. How many phones have you broken and/or lost?

Some people are clumsier than others. Is your boyfriend clumsy? Find out by asking him how many phones he’s gone through.

His answer might really shock you… And convince you to buy him a phone case!

57. What is the most useless thing you know how to do?

There are people out there who know how to throw a bowling ball with the perfect spin to guarantee a strike every single time. And if you ask them how useless this skill is away from the bowling alley, they’ll tell you not at all!

What’s one useless skill that your man has? Find out by asking him this funny question.

58. What gamble have you taken that’s really paid off?

Not many people ask this question, but if you ask your man about what gamble really paid off for him, he’ll really appreciate you for asking.

Who said that these funny questions to ask a guy couldn’t also strengthen your bond? [Read: How to be fearless – 18 ways to set aside fear and live like a champion]

59. What’s the biggest mistake in history?

Asking someone about the biggest mistake that they’ve ever made? That’s a very touchy subject. But asking someone what they think the biggest mistake made all throughout history is? That’s a very interesting subject that you could talk about for hours!

The conversation will be even better if your man is a serious history buff.

60. How much of a handyman are you?

Bust out this weird question to ask a guy to find out how handy your boyfriend or date is. Who knows, you might need him to help fix something around your house someday.

[Read: 94 seriously deep, revealing questions to ask a guy and get to know him ASAP]

61. If you were a potato, how would you like to be cooked?

Exploring a person’s preferred method of potato preparation can be a quirky gateway into understanding their sense of humor and preferences. If he chooses “mashed”, for instance, does he love comfort food? If he says “fries”, is he all about the crunch in life?

This light-hearted question is an amusing way to broach the topic of food and cooking without diving deep into culinary arts.

62. Would you rather fight one horse-sized duck or a hundred duck-sized horses?

This classic hypothetical taps into the analytical part of the brain. Does he strategize? Does he pick the single giant duck because it’s one opponent? Or does he assume the little horses are more manageable?

This is a delightful way to see how someone problem-solves and perceives challenges, even in a fantastical context.

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

Beyond just being fun, this question can inadvertently pull out preferences and dietary inclinations.

Someone choosing “green”, for example, might be health-conscious *thinking of veggies* or just really into mint ice cream! It’s an unusual way to touch upon dietary habits and favorite foods. [Read: Cooking as a couple – romantic tips and date ideas to have fun together]

64. Which wild animal do you think you could reasonably befriend and why?

The chosen animal might reflect some aspects of his personality or desires. Maybe he’d befriend a lion because he values courage, or perhaps a sloth because, let’s face it, who doesn’t want more nap times? This offbeat question can provide a fun insight into his self-view and aspirations.

65. If aliens landed tomorrow and you could be their tour guide for a day, where would you take them first?

This question gives a glimpse into what he values or finds intriguing about our world.

Would he show them the Grand Canyon for its natural beauty, or a bustling city to showcase human achievement? The places that come to mind first can be telling about his interests and priorities.

66. If you had to replace your hands with objects already in your house, what would you pick?

Diving deep into someone’s home environment and creativity, this question mixes the surreal with the practical.

It’s a perfect balance between funny questions to ask a guy and making him think about the ordinary in an extraordinary way.

67. Which cartoon character do you believe you’d get along with best and why?

Cartoons often reflect exaggerated versions of human traits. By pinpointing a cartoon character, you get a fun insight into what traits or personalities he finds appealing or relatable. [Read: 20 unromantic movies with surprisingly romantic twists]

68. Imagine humans evolve to have a third arm. Where would you want yours?

This weirdly funny question taps into the imagination while also playfully addressing human anatomy. Would a third arm on the back be for surprise high-fives or one on the leg for… extra balance?

69. If you were a ghost, where would you haunt and who would you spook the most?

Dabbling in the supernatural, this question gives a guy the chance to showcase his mischievous side or perhaps reveal a place that holds special significance to him.

70. How would you feel leading a parade dedicated to the most mundane thing you did today?

This funny question to ask a guy combines daily routine with the absurdity of celebrating the ordinary. It’s a delightful way to poke fun at our habits while imagining them on a grand scale. [Read: How to be grateful – 20 authentic ways to appreciate and express it]

71. What’s the most useless talent you have, and how do you think it could save the world?

We all have those quirky, seemingly pointless skills. By framing it in a world-saving context, this question adds humor while highlighting each of your unique personal quirks.

72. If animals could talk, which one do you think would be super annoying?

Another question blending reality with fantasy, this one allows a guy to share his perceptions about certain animals in a humorous, anthropomorphic light.

73. If you were to win an Olympic gold medal for a completely mundane task you do daily, what would it be?

A fun twist on the ordinary, this funny question to ask a guy would have him re-evaluate his daily routines and regard them as world-class skills.

74. Which movie villain do you think you’d get along with and why?

This one dives into the realm of cinema and psychology. While it’s a lighthearted question to ask a guy, it can shine a light on his perceptions of right, wrong, and the gray in between.

75. If every time you snapped your fingers, a random item of clothing would change color, what’s the first thing you’d snap at?

A quirky take on fashion, this question allows for a whimsical exploration of style preferences and the joy of unpredictable aesthetics. [Read: 44 outfit tips and secrets on what to wear on a first date for girls and guys]

76. What song title best describes your last trip to the bathroom?

Now, this funny question to ask a guy might get a few giggles and blushes! It’s lighthearted and brings a touch of humor to life’s most natural moments.

77. If you could have any fictional character as your wingman/wingwoman on a night out, who would it be?

Blending the world of fiction with real-life scenarios, this question provides insights into the personalities or traits he values in friends. [Read: 37 secrets to be the best wingman and help your friend hook a great girl]

78. Imagine every sneeze turns you briefly into an animal. Which sneeze-to-animal transformation would be the most inconvenient for you?

A bizarre and hilarious scenario! This funny question to ask a guy would certainly make for an entertaining discussion about animals and timing.

79. If you were a kitchen appliance, based on your personality, which one would you be?

Drawing parallels between personality traits and everyday items, this is a delightful way to connect human characteristics with the inanimate.

80. If you could give one piece of clothing to everyone on earth, what would it be?

A hat? A funky tie? This funny question to ask a guy is a great way to delve into his fashion sense, while also getting a glimpse into what he thinks might unite *or humor* humanity. Also, it’s a fun mental image to think of everyone wearing the same thing!

81. What’s the most awkward thing that’s happened to you while shopping?

Most of us have an embarrassing shopping story. This question will not only allow him to share a laughable moment but also give you insight into his ability to handle unforeseen situations. A hilarious way to bond over shared human experiences!

82. Would you rather always have to wear clown shoes or a propeller hat?

Asking someone to pick between two equally silly options is why would-you-rather is always a fun game! This funny question to ask a guy can lead to a conversation about fashion, comfort, and the lengths one would go for a laugh.

83. If you were the ruler of a small island nation, what would be the national holiday you’d invent?

A day dedicated to napping? Or maybe a chocolate appreciation day? This question is a fun way to explore his imagination and values, all while having a good chuckle.

84. How would you react if every time you opened your mouth, your voice sounded like a famous singer?

Whether he ends up sounding like Barry White or Taylor Swift, it’s a fun and quirky way to discuss music preferences and how life would change with a constantly tuneful voice.

85. If a genie offered you unlimited storage space in your pockets or unlimited gas in your car, which would you choose?

An oddly practical yet hilarious question to ask a guy. It’s amusing but also hints at his lifestyle preferences and priorities.

86. Which fruit do you think would be the most fun to be for a day?

Walking around as a bunch of grapes or a tall pineapple? It’s a hilarious image and also a lighthearted way to discuss likes, dislikes, and the quirks of nature.

87. If you were a professional wrestler, what would your entrance theme song be?

A person’s musical preference can tell us a lot about them. This funny question to ask a guy lets you delve into his music tastes, while also imagining a dramatic and entertaining scenario. [Read: Falling in love – 50 perfect songs to enjoy that happy rush]

88. How would you feel if your life was narrated by a famous comedian?

Imagine life’s ups and downs being narrated by someone like Kevin Hart or Ellen DeGeneres—how could you ever be down again?! This question is a great way to discuss humor styles and how one perceives their own life.

89. Which fictional universe would you absolutely not want to live in?

While watching our favorite show or reading our favorite book, we’ve no doubt spared some thought towards what it would be like to live in that universe.

We’ve surely all imagined ourselves taking walks in the fantastical wildlife, making friends with the main characters, and getting into all sorts of trouble within the world of our favorite creation.

But why ask a guy about the fictional world he would want to live in when you can ask him about the world he absolutely would not want to visit? Sure, this makes for a weird question to ask a guy, but it opens up discussions about books, movies, and personal comforts.

90. If you could have dinner with three famous people—dead or alive—who would make the dinner most awkward?

Once again, sometimes the best and funniest questions to ask a guy are the ones that subvert all expectations! This question makes for a fun twist on a common question, leaning more toward humor and quirky interactions.

91. How would you react if you found out your life was a reality show watched by aliens?

A blend of sci-fi and humor, this question is sure to spark laughter and creative speculations.

92. What’s your secret move on the dance floor?

Every guy has that one move, whether it’s the robot or the worm. This funny question to ask a guy is a lighthearted way to chat about parties, music, and dance.

93. If you were a superhero, what would be your not-so-super power?

The power to instantly cook pasta? The strength to carry in all the groceries in one trip? This question may seem mundane, but it’s actually a fun, imaginative way to chat about strengths, weaknesses, and the joy of the ordinary.

94. Which animal do you think you’d be inexplicably scared of if they could speak?

Maybe squirrels have a lot of complaints? Maybe dogs aren’t as innocent and friendly as we thought? This funny question to ask a guy makes for a delightful dive into the world of animals and our perceptions of them.

95. If there was a sandwich named after you, what would be on it?

This question is a direct way to find out exactly what makes up this guy, even if just in a culinary sense. You guys could also take turns coming up with names for your sandwich personas!

96. How would you feel if you woke up one day and all your left socks had disappeared?

A quirky take on everyday mysteries. After all, who doesn’t have a sock that’s gone missing?

97. If you were tasked with renaming the colors of the rainbow, what would you call them?

A fun exercise in creativity and perception of the world. Just don’t forget to come up with your own answers and compare them to see how similarly you two see the world!

98. Would you rather have to start every sentence with “Hey, remember that time when…” or end every sentence with “…but I could be wrong”?

A quirky language-based question that’s bound to get some chuckles. Who knows, maybe he already talks like this!

99. 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. After all the funny questions you’ve asked him, he should think of some fun questions to ask you too. After all, it’s not your responsibility to carry this date.

It’s the Playful and Unexpected That Leaves the Most Lasting Impression

Having a collection of funny questions to ask a guy can truly be a conversation game-changer, showcasing your wit and charm. It’s these lighthearted moments that can help forge a deeper connection.

Establishing a rapport based on humor not only brightens up the interaction but also sets the stage for deeper connections and, potentially, winning his heart.

[Read: 60 deep, fun questions to get to know someone romantically as a match]

So, always keep these funny questions to ask a guy at the ready. Dive into them during those quiet moments, and you’ll find that awkward silences will be a thing of the past. Remember, sometimes it’s the playful and unexpected that leaves the most lasting impression.