We’ve posted about the sorts of questions you can ask to get to know someone, plenty of times, but this list is specifically for questions that will make both of you laugh. You have to be daring to ask a lot of these, and you have to be willing to answer them yourself, too. Having a compatible sense of humor with someone is so great in a relationship, and laughter brings people together. Here’s thirty laughter-inducing questions to get your crush laughing, pinpoint his sense of humor, and learn some surprisingly intimate things about him. Here are our top 30 funny questions to ask a guy!
11 What song would you play on repeat if you had to torture someone?
We all have that one song that just sounds like nails on a chalkboard to our ears, for whatever reason. This phenomenon is so universal that AVClub.com has an interview series called, “Hatesong,” dedicated to asking guests, “to expound on the one song they hate most in the world.” The results are hilarious. Have your own little “hatesong” dishing session, because when someone has a harmless, irrational hatred for some silly thing like a random song, it’s super funny.
1. What song would you play on repeat if you had to torture so...
22 What’s your favorite animal sound?
Throw this one out there without warning. Seriously. It will never be relevant to any conversation you could possibly have, so there’s no right time to say it, but it’s weird and oddly thought-provoking AND it might prompt one or both of you to impersonate an animal, which is the funny part. This question requires you to be super comfortable with your weird side.
2. What’s your favorite animal sound?
33 What would you choose as your animal sidekick if you were in a movie?
Do not accept “dog” as his answer. That is boring. You can also press him, “Why not a hyena?” and offer up your own opinion: “I’d want an angry porcupine.”
3. What would you choose as your animal sidekick if you were i...
44 Would you still talk to me if my face looked like this?
And then make an hold a crazy face while he tries to answer without laughing. You can sub in, “If my voice sounded like this,” or something similar.
4. Would you still talk to me if my face looked like this?
55 What’s the worst date you’ve ever been on?
Most people have one or two awful date stories that are only funny in retrospect (because it definitely wasn’t funny while you were stuck in that awful tapas bar with that insufferable guy who wouldn’t stop making his political case for why he specifically refuses to open doors for women even though you never would have noticed but now he has forced you to acknowledge what a tool he is). Share those and laugh at yourselves, now that you’re safe from your terrible dates.
5. What’s the worst date you’ve ever been on?
66 If you had to do one for a week, would you rather paint your nails hot pink or wear eyeliner?
This one is both a funny question and a test. If he freaks out at this question, that’s something of a red flag. It’s silly and theoretical- under what circumstances would his life depend on eyeliner or nail polish? None ever.-so if he takes offense or refuses to answer or gets defensive, he’s no fun and, in my humble opinion, insecure.
6. If you had to do one for a week, would you rather paint you...
77 If you had to get a tattoo on your arm in tribute to a food item, what would it be?
You know those iconic heart-and-scroll tattoos with someone’s name on the scroll that you see all the time in cartoons and movies? Yeah, one of those, except in tribute to pizza, or falafel, or whatever. Sub out the heart for the food item, too.
7. If you had to get a tattoo on your arm in tribute to a food...
88 What’s your mutant superpower?
By this question, you’re not asking “IF you could have a mutant superpower…” you’re asking what he already has. Obviously none of us can control metal with our minds or blow things up with our eyes, but do you have a weird, funny, or uncommon skill that you never had to work for? Most people can think of something they’re uncommonly good at. That’s what this question is getting at.
8. What’s your mutant superpower?
99 What would you demand be done/given to you everywhere you go if you were famous?
Because we all know that celebrities can make strange demands about what is in their dressing rooms or what kind of service they get on airplanes. We laugh and call them spoiled, but y’all, don’t you sort of wish you could make sure there was an unlimited supply of your favorite drink on hand everywhere you went? Admit it!
9. What would you demand be done/given to you everywhere you g...
1010 How would you take down Kanye West’s ego?
An impossible task, we all know, but you might as well brainstorm.
10. How would you take down Kanye West’s ego?
1111 What crazy name would you give your kid if you were a celebrity?
Okay, some of the celebrity baby names that seemed weird when the kid was first born (Apple Martin-Paltrow, for example) are actually pretty cute now that we’ve gotten used to them, but let’s not forget that musician Frank Zappa had children named Moon Unit, Dweezil, and Diva Muffin (seriously) and I will never get over that. But if you could get away with it on account of fame, what would you name a kid?
11. What crazy name would you give your kid if you were a celeb...
1212 How would you hide if you suddenly became naked right now?
Please don’t spring this on anxious types, because “naked in public” is such a common nightmare. If you’re getting to know someone and generally find him pretty chill and relaxed, and you feel bold, you can challenge him with this one.
12. How would you hide if you suddenly became naked right now?
1313 What’s your biggest dealbreaker with a girl?
He might have a funny answer to this one: sometimes, a dealbreaker is a weird feature that raises concerns about a person’s character, but is, by itself, seemingly innocuous, or it really is innocuous, but just drives you, personally, crazy. You’ll also get a good look at his values and tastes. File away his answer as food for thought. If he gives an answer like, “stretch marks,” that kind of attitude is probably a dealbreaker for you.
13. What’s your biggest dealbreaker with a girl?
1414 What book would you banish from high school reading lists?
Am I the only one who feels like high school reading lists are stuck in the 1950s? How is it that schools are still teaching soooo many of the same old, dated books, when new books are coming out all time? There have got to be some new classics out there! And I HATED Catcher in the Rye. I’m willing to bet everyone who paid attention enough to care has a book they hated above all others in high school English class. Let loose on that dated classic. I have a BA in literature, and you have my absolute permission to hate on any book you want.
14. What book would you banish from high school reading lists?
1515 What class would you make everyone take in high school?
Alternately, “What do you wish they’d taught you in high school?” This question is funny because as we grow up and get out into the world, in college and beyond, we all have moments when we learn something and think, “OMG, how did I not know this already?” It’s often a basic life skill a fact of our daily lives. And it makes us feel really stupid. And if you can laugh at yourself, do it.
15. What class would you make everyone take in high school?
1616 What’s your guilty pleasure music?
I’m no fun because I always refuse to answer this question. Most people, however, like getting permission to spill that they can’t get enough of some embarrassing album. For the love of people like me who are so tight-lipped about this question, don’t give him too much of a hard time about it when he cops to liking the Backstreet Boys or whatever.
16. What’s your guilty pleasure music?
1717 If it had to be something in this room, what would be your zombie apocalypse weapon?
Don’t ask him this in a Walmart. Ask him this in someone’s living room, or a coffee shop, or a classroom. Make him get resourceful.
17. If it had to be something in this room, what would be your ...
1818 What was your dream job when you were five?
For most people, the answer is pretty funny. I wanted to be a paleontologist, which is a really, really serious answer for someone who can barely tie her own shoes and has no concept of the level of work involved in getting a PhD. It’s hilarious to look back on the stuff we thought we wanted as kids, and compare it to where we are now.
18. What was your dream job when you were five?
1919 Who was your idol when you were five?
Similar to the previous question, but way more potential comedy.
19. Who was your idol when you were five?
2020 What do you wish was the same now as when you were five?
Because youth is wasted on the young! Only now do we understand the incredible gift of dedicated nap time and snack time. What would he give anything to have back from that age?
20. What do you wish was the same now as when you were five?
2121 What did you lie about when you were five?
I’m so glad Youtube wasn’t a thing when I was five, because I’m sure my parents would have been sharing all the stupid and crazy stuff I said as a kid. Remember that kids don’t really have a concept of lies until a certain age, and then they do it badly with hilarious results.
21. What did you lie about when you were five?
2222 What would your grandmother be horrified to learn about you?
This works because we hold our grandparents to a very different standard than our peers. There’s lot we’re open about among friends and younger family members that are totally off-limits to our grandparents. It doesn’t need to be a super serious answer because chances are, you already know the thing that constitutes a terrible secret to Grandma Milly.
22. What would your grandmother be horrified to learn about you...
2323 What’s the stupidest way you’ve ever hurt yourself?
I know a few tall guys who have stood up and walked straight into a ceiling fan. I can also admit to some totally avoidable bicycle-related mishaps that left me pretty banged up. This is another thing that’s only funny in retrospect, but it’s still a little embarrassing, so you’re getting him to open up. Bonus: he might show you a scar.
23. What’s the stupidest way you’ve ever hurt yourself?
2424 What fictional character would you marry?
WE ALL HAVE AN ANSWER TO THIS! We ALL have an answer, but it’s still kind of embarrassing and funny to be asked and have to answer.
24. What fictional character would you marry?
2525 On a day held in your honor, what would people have to do?
What would they have to eat? What events would be held to celebrate your life and values? He gets to decide what counts most about him, and what would make for a good party.
25. On a day held in your honor, what would people have to do?
2626 What food combination do you want to ban?
This is funny because it’s a highly specific pet peeve, and most people have an answer that they’re bursting to tell. It’s usually something really common and accepted that we just can’t stand, so we encounter it all the time.
26. What food combination do you want to ban?
2727 What’s your first executive order as king of (this coffee shop, this grocery store, this room)?
Give him absolute power, but only over a very small kingdom. Within that small kingdom, he gets to make one thing law, whether or not it’s especially relevant to the place in question.
27. What’s your first executive order as king of (this coffee s...
2828 If you had to flee the country, where would you choose to live?
This is a more interesting/funny way to ask, “If you could move anywhere in the world, where would it be?” That’s a legit, interesting. telling question, but it’s a little cliche. It’s way more fun to imagine yourself as a fugitive on the run.
28. If you had to flee the country, where would you choose to l...
2929 What would your new identity be?
Once he’s decided that he’d flee the law by moving to Calcutta or wherever, who will he become to keep his identity as a fugitive secret? This is a good question if you want to know how to keep a conversation going and also make him laugh.
29. What would your new identity be?
3030 If I were your personal slave, what would you make me do?
This brings you into the equation, and yeah, he might say, “my dishes,” but he might say something more fun and cheeky. You tell him you do whatever he wants, and see how he takes it, where his mind goes.
30. If I were your personal slave, what would you make me do?
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