30 Funny Questions to Ask a Guy You Like

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.

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.

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.”

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.

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.

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.

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.

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.

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!

An impossible task, we all know, but you might as well brainstorm.

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?

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.

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.

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.

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.

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.

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.

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.

Similar to the previous question, but way more potential comedy.

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?

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.