Best 40 Funny Questions To Ask A Guy

Want to learn more about your new guy and have fun, too? Ask him these 40 funny questions, and get to know each other better!

By Olive Winks
Best 40 Funny Questions To Ask A Guy

Understanding What A Guy Finds Funny

Funny is sexy. Period. Most guys, regardless of their background, professional status, or personality, will tell you that yes, looks are important, but so is a good sense of humor. So ladies, if you are funny and can make your new guy laugh, it will only strengthen his attraction to you, and make him more likely to be interested in a long-term relationship. And what's the best way to get to know each other? Questions, questions, and more questions. So to help make your guy laugh, we came up with 40 funny questions. Some of these are silly, some are smart, and some are a bit weird. But all of them will help the two of you laugh together, and, hopefully, take your intimacy to the next level.

Weird Dates, Nudity, Reality TV: Funny Questions

1. What professional sport would be funny to see played naked? Let's face it: most guys love sports and games. And being visual creatures, they enjoy nudity too. If you're part of a couple, this is a funny question to ask as it'll give you much more insight into your guy's personality. Get a funny answer like "Women's tennis," and you'll know your beau has a playful and flirty side. If his face reddens and he avoids eye contact, you have a shy one on your hands, which is totally adorable.

2. What is the most embarrassing piece of clothing you've ever worn? No matter how cool and sophisticated your guy is, he'll want to tell you about the time he lost a bet with a friend and had to wear a dress. Or about the time he bought and wore a funny hat or T-shirt because he'd seen some celebrity wear the same one.

3. What activity is made funnier by alcohol? Alcohol is fun...and funny, making this another rich topic to explore. Guys, especially playful and funny ones, enjoy a beer or a cocktail now and then, and they'll think of several activities and games that would be made even more fun with the introduction of alcohol.

4. What is the weirdest thing you've ever had happen on a date? Being part of a couple, in particular, a long distance couple, you need to spice things up occasionally, and this is a funny question to ask. Every guy has a dating war story, some several, so ask him this question. After he stops laughing, he'll most likely tell you a very funny story. Just be prepared to be asked a barrage of funny questions in return!

5. What is something that everyone looks funny doing? Questions like these always make me laugh because there are a lot of places your guy could go with the topic. But chances are, this one will get him scrolling through his mental list of funny activities. And who knows? Maybe he'll have some questions for you, like why do you think even George Clooney would look funny when sneezing?

me when i'm showing off my muscles😂 #steveurkel #muscles

A post shared by steve urkel (@__steve__urkel__) on

6. What funny TV character do you most resemble? Your average guy has thought about this question (and other questions about celebrities) at least a little bit. So when you ask him, pay close attention to his answer. I definitely plan on asking my guy what funny TV character he resembles on our next date night...and I hope he says Patrick Dempsey. I definitely have a few questions for Dr. McDreamy from Grey's Anatomy!

7. If you were in a reality TV show, which one would it be? Ever since Survivor burst on the scene like a million years ago, people have been obsessed with reality TV, and your guy, although he may deny it, watches these funny shows occasionally. So ask away, and don't be surprised if he gives you a detailed, well-thought out answer.

Celebrity Crush and Bad Pics: Funny Questions

Thank you @rollingstone

A post shared by @ harrystyles on

8. If you could spy on your celebrity crush, who would it be, and why? Two funny questions in one! Whether your guy is into blondes or brunettes, skinny girls or curvy, he has a favorite starlet. Ask him about who she is, but be forewarned, girls: if you're part of a couple, particularly if you're in a long distance relationship, don't fret over his answer. He's still into you. Celebrity crush is just a funny game to play. Unless that is, he shows you a secret room devoted entirely to Scarlett Johansson. That would be a major issue, and certainly require a lot more questions from you.

9. If someone were to make a reality TV about your life, what would it be called? Yes, even those masculine guys that drink beer, watch sports, and work out everyday have wondered what it would be like to star in a reality TV show. You might be surprised by your guy's answer. You might also be surprised when he asks questions such as, "Would I be the star, or just a sidekick or recurring character?"

10. What super power would you like to have, and why? Not all guys are into comic book characters and action movies involving superheroes and villains. But they still have spent at least some time thinking about having superhuman strength, being invisible, or my personal favorite, being able to fly.

I need to stop comparing myself to others, because it just brings me down

A post shared by Sunshine (@strangetalents) on

11. If your life depended on you impressing a gun-toting criminal, what talent of yours would you use? You never know what funny talent or strange skill a guy has until you ask. And nothing brings out our best (and worst) like a near-death experience. Just be advised: if your guy says he is a world-class break dancer, that's cool, but if he says he plays the recorder or secretly sings backup vocals in a Backstreet Boys cover band, you should run!

12. What is the weirdest/funniest compliment you've ever gotten from a girl? This question will give your guy the opportunity to brag, or blush, or laugh. I once told a guy that I would walk on hot coals for his really long eyelashes. And guess what? He laughed, and we dated for six months. Just don't ask us how it ended because that wasn't funny.

A Girl For a Day...Too Funny

13. Describe the biggest screw up you ever made and got away with it. Whether your guy is a leather jacket-wearing, motorcycle-driving bad boy, or a responsible librarian with an impressive collection of suspenders (how adorbs would that be?), he has a good screw-up story to tell. If you're in a long-distance relationship, ask these types of questions because they help you bond over your respective failures. Why? Because failure is funny.

14. What's the funniest thing you'd do if you were a girl for a day? What a fun game to play! Who wouldn't want to answer this funny question? Maybe he'd want to try on dresses, or wear makeup, or just (try) to walk around in high heels. Either way, he may ask you a million questions, starting with, "How the heck you do this?"

15. Describe your worst/funniest school picture. Like girls, most guys have had an awkward phase, and your guy certainly has the yearbook photograph to prove it. If your guy is cool and fun, he'll tell you about his worst picture and then laugh it off. And, if you're really lucky, he may even show you the picture. The only real question is, will you show him your funniest yearbook photograph? Me, I would. How could I ever forget Mrs. Gretchen's fourth grade class at Old Richmond Elementary?

Guys Waxing Eyebrows...Very Funny

16. Have you ever waxed your eyebrows? Guys are very curious about the grooming habits and routines of girls, but they are reluctant to ask those types of questions. This is a good question to ask if you're part of a couple, especially if you're in a long-distance relationship. And trust me when I say, your guy has definitely wondered about waxing eyebrows.

17. Have you ever pretended to like something just because someone you wanted to impress liked it? Get your guy to answer this funny question, and you'll get some interesting intel about his personality and, perhaps more importantly, his willingness to please you!

Henny & Fruit Loops is a deadly combo😂😈 @supremechubz #lildickgang

A post shared by Supreme Patty (@supremepatty) on

18. What is the funniest drinking game you've ever played? Drinking, when done in moderation, is a fun and social way to get to know new friends or strengthen long-term relationships. That said, we all have, at one time or another, drank too much, and if your guy is anything like me, the time he overindulged probably started with a silly drinking game. For better or worse, drinking games can provide us all with some fabulously funny stories. So make sure to ask these alcohol-related questions early and often.

19. Describe the grossest drink you've ever tasted. Have you ever mixed orange juice and milk? Or spiked your coffee with tequila (I will plead the Fifth Amendment if asked about this one!)? The truth is when groups of guys get together, they do outrageously dumb stuff. Like fill used ashtrays with stale beer and strawberry milkshakes, and then dare (or double-dare) someone in the group to drink it. Now ask yourself this: do you want to miss out on an opportunity to hear about those horror stories? No? Then ask your guy this funny question, and be prepared to soil yourself laughing.

Best Thing About Being a Guy? Funny Answer

20. If you could cast only one spell, what would it be? Hopefully, your guy will say, "I would cast an undying love spell on you." But even if he doesn't, he'll most likely say something interesting, something that the two of you can laugh about. This is another one of those questions that sound silly but yield funny answers.

21. What is the best and worst thing about being a guy? Ohh, I love these best/worst questions. They're always ripe with potentially funny and unexpected answers. This one would be interesting to ask any guy, whether he's a man's man, a shy guy, or a bad boy.

Mermaid dancing, commence! #PitchPerfect

A post shared by Pitch Perfect (@pitchperfectmovie) on

22. What movie do you wish life was actually like? Some guys like action movies with car chases and big explosions, while others prefer psychological thrillers where nothing (and no one) is as it seems. But regardless of what kind of movies your guy likes, he has a favorite, and he has a reason for his favorite. Ask him and sit back and listen to him wax poetic about why life would be so much more interesting if it was like Inception. As for me, that's easy: I wish life was like Pitch Perfect!

23. What was something you were really into when you were young, but now think is dumb? To give you an example of the potential comedic goldmine that is this question, here's how I would respond. When I was seven, I was obsessed with Jessica Simpson and tried to dye my hair bleach blonde, just like the former pop star. Needless to say, my hair turned a very strange orangish/green color, and my mom grounded me for an entire month. Epic fail!

24. What is the strangest thing you've ever bought? This just in: males are totally weird, and I love it! I guarantee your guy has something odd that he bought sitting in his closet. Pretty please, ask your guy this question. You won't be sorry.

Money, Money, Money

25. What wouldn't you do for one million dollars? Whoa, this funny question could yield some seriously crazy and entertaining answers, not too mention lead to a series of much-needed follow-up questions. Oh, to be a fly on the wall when you ask your guy this one!

26. What is the best pick-up line you've ever used or heard of? Spoiler alert: guys will say just about anything to get our attention. In fact, I had a boyfriend once who confessed that he'd spent hours in front of a mirror rehearsing pick-up lines...one of them he used on me. Guess it worked, because we're still together three years later. Now if only I can get an engagement ring out of him...

27. What was the strangest habit you had as a child? Come on, people. We all had them, so just fess up, and then we can all laugh about it. Yes ladies, even your guy, who is too-cool-for-school and way hot, had a weird habit when he was a kid. I played a silly game called Olive's World where I pretended to have my own talk show like Oprah's. Totally embarrassing.

Sooo Embarrassing

28. Describe your most embarrassing moment from high school? Here's another potential goldmine. Personally, I have so many I should write a book, but wait, I'm already doing that! Ask your guy this question, and catch a glimpse into what he was like back in high school.

29. Describe the most elaborate prank you've ever played on someone. I have some inside dirt on this: practically all of my friends in college were guys, and when they weren't drinking beer, skipping class, or chasing girls, they were either planning or executing elaborate pranks on their friends. Really, I never laughed so hard, so ask your guy this question.

Need Funny Questions...Head To The Movies

30. No matter how late it is or tired you are, what movie will you stop and watch if it's on TV? Guys love movies. All guys. It's a fact. Not up for debate. And, in my experience, guys are passionate about the movies they love, and they can, in the right setting, wax poetic about Point Break or The Godfather. It's tots adorbs. But again, be prepared to be peppered with questions like, "Why haven't you ever watched Blade Runner?" and "Do you really think 10 Things I Hate About You is a good movie?"

31. Name something you're really, really bad at and will never do again, no matter what. For me, this is one of the easiest questions to answer. In a word: karaoke. Well, I've confessed. Now all you have to do is ask your guy this funny question, and get him to spill the beans.

32. If you had the choice between being the ultimate superhero or the ultimate villain, which would you be? Another one of those questions your guy will love. Whether he wants to be naughty or nice, your guy will say something funny in response. Be prepared to bust a gut.

33. Describe the funniest date you've ever been on. What made it so fun? Definitely one of those perfect questions to ask a guy with whom you've just started dating. His answer will give you an idea what he's into and what he thinks is fun. My advice, take notes.

Know Any Billionaires?

34. A billionaire gives you $200,000 to make any room in your house or apartment amazing, what room would you choose, and what would you do to it? Bit of an odd question, but remember, guys love to daydream about building their own Man Caves, so they can watch football and drink beer and wear sports jerseys. And I say, "Have at it, guys!" If your guy does build his dream room, I'd ask him two questions. One, where can we install the wine fridge? And two, can we get an extra plasma TV that stays on Bravo 24/7? Please and thank you!

35. Who would be the worst celebrity to have dinner with? I definitely have some thoughts on this question, but I'll bet your guy does, too. Plus, this is just one of those fun games to play.

36. What is the silliest thing that you know way too much about? Guys also tend to have obscure or strange hobbies or interests. Take my first boyfriend, for example. He spent a lot of time practicing impressions of famous singers like Michael Jackson and Bruce Springsteen.

Boys Versus Girls

Follow @ash_mimu

A post shared by Bangladeshi boys and girls (@bd.boys.and.girls) on

37. What is the biggest difference between girls and guys? This one, I think, speaks for itself. Lotta different funny answers could come from asking your guy this question.

38. If you were to bury three funny things in a time capsule to be dug up in 100 years, what would they be? It's always fun to see what funny things people might bury for future generations.

39. Which would you be more confident doing in public: competing in a dance competition, or a karaoke contest? Two words: DANCE OFF! But I'm sure there will be follow-up questions ranging from "How many times are you going to do the Shopping Cart?" to "Will you stop doing the Roger Rabbit, please?"

Bad websites are like bad fish dinners! #gross #badwebsitedesign #fishpie #badwebsites

A post shared by AR Design (@ardesigners) on

40. What's one website you would be embarrassed if people found out you visited it? Buckle up before asking your guy questions about his Internet usage. There's no telling what he might say. And by the way, if he refuses to answer, suspect the worst, and by worst, think: weird porn sites.

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