Weird Questions to Ask a Guy
Weird questions to ask a guy when you want to knock him off his usual answers and see how his mind works, in person or over text. The 80 questions run in the order you would use them: Warm-ups, Food and animals, Habits and brain, What if, The two of us and Over text. All of them are strange but harmless, and each note says what a good answer sounds like, how to keep the bit going, or whether he needs to know your humor first.
Want questions from the whole vault instead? Try the random question generator.
The questions
Each question, and why to ask it
Warm-ups
A hundred duck-sized horses or one horse-sized duck: which fight are you taking, and what's the plan?
Why ask it
Everyone has heard it and hardly anyone has been made to explain tactics, so the plan is where it gets good. Listen for the moment he starts worrying about the big duck's beak, then ask which he would pick if he had to fight in flip-flops.
What's the weirdest thing you believed until an embarrassing age?
Why ask it
The pony that grows up into a horse, the ice cream truck that only plays music when it has sold out: he has one, and it probably lasted into double digits. Ask who finally set him straight and how he took the news.
If you were a ghost, would you be the scary kind or the kind that only moves the remote?
Why ask it
Petty usually beats scary, and the details arrive fast: one sock taken from every pair, the thermostat nudged by a single degree. Who he would haunt first, and what unfinished business is keeping him around, are the next two questions.
What's the smallest animal you're fairly sure would beat you in a fight?
Why ask it
An honest guy says a goose and does not need to be pushed. If he claims nothing under dog size could take him, walk him up through a swan, a raccoon and an angry house cat until he concedes one.
What's in your room right now that would be hardest to explain to a stranger?
Why ask it
He can look around and answer truthfully, which is why it works on a guy who says he is not weird. Over text, ask for a photo and guess the story before he tells it.
Aliens, ghosts or Bigfoot: which one would you bet real money on?
Why ask it
Making it a bet forces a ranking, and the reasoning is the fun part: space is big, forests are big, old houses creak. Then flip it and ask which of the three he would least like to meet on the walk home.
What's the dumbest conspiracy theory you secretly enjoy?
Why ask it
Keep him at the silly end, where mattress stores are a front for something and birds are suspiciously well organized. If he drifts toward one that people get angry about, say 'no, the dumb ones' and he will usually come back.
What's the strangest compliment anyone has ever given you?
Why ask it
'You have a trustworthy walk' or 'nice elbows' stays with a person for years, and he will quote it exactly. Find out who said it, then give him an odd one of your own to add to the collection.
What was your weirdest phase as a kid?
Why ask it
Photos usually exist and a parent usually has them, whether it was the year of the cape or the months he was a dog at dinner. How it ended is the part to get: some phases stop overnight, and some he never fully left.
Did you ever have an imaginary friend, and what happened to them?
Why ask it
The second half is where it turns strange, because imaginary friends move away, get replaced or are simply never mentioned again. A guy who had none can tell you what he named his bike or the family car.
Which mythical creature would make the worst roommate?
Why ask it
A dragon and the heating bill, a mermaid and the bathroom schedule, a werewolf and the security deposit. Once he has ruled a few out, ask which one he could actually live with and what the house rules would be.
What's the strangest thing boredom has ever made you do?
Why ask it
Easy to ask early, since nothing boredom makes a person do is really his fault. 'How long did you keep it up?' gets the rest: the ceiling tiles were counted twice, or the juggling lasted a whole summer.
If you could add one pointless law that everyone had to obey, what would it be?
Why ask it
Good answers are harmless and oddly firm: everyone waves at buses, no socks on Thursdays. Ask how it would be enforced and what the fine is, and he will build a whole government around it.
Food and animals
Hot dog: sandwich, taco, or its own thing?
Why ask it
Adding the taco gives a guy who is tired of this debate something new to chew on, since the bread is hinged at the bottom. Whatever he rules, test it on a sub roll and a folded slice of pizza.
Is a Pop-Tart a kind of ravioli?
Why ask it
Filling sealed inside a crimped pocket of dough: the case is stronger than he wants it to be. A good answer comes with a definition of ravioli, which you can then attack with a dumpling and a calzone.
What two foods do you put together that nobody else at the table would touch?
Why ask it
He will defend it before you have said a word against it. Promise to try it once if he tries yours, which gives you both a small dare to carry out the next time you eat together.
What did you eat as a kid that you can't believe you ate?
Why ask it
He remembers exactly how it tasted, so have him score it out of ten. A dog biscuit usually does better than he expected at the time, and the candle that smelled like vanilla never does.
What food do you eat in a way that would upset people?
Why ask it
Biting across all four fingers of a chocolate bar, peeling a banana from the wrong end, taking a string cheese in bites. If he does not see the problem, describe your own method and find out who is more appalled.
If you were a kind of potato, which would you be: fries, mashed, baked or a tater tot?
Why ask it
A good answer has a reason attached, like baked because he takes an hour to be ready for anything. Tell him which one you would have guessed for him, and be prepared to hear what kind of potato you are.
You get one dinner made entirely from gas station food. What's on the tray?
Why ask it
This shows his road trip habits more than his taste, and he will be very sure about which chips. Disagree with one item only, so the argument stays small and lasts a long time.
Which animal do you think is secretly the smartest, and what is it planning?
Why ask it
Crows, octopuses and raccoons are the strong picks, and the plan is where he has to improvise. A guy who answers 'my dog' should be asked for evidence.
Which animal looks like it was put together from leftover parts?
Why ask it
The platypus is the usual first pick, so ask for a second, and you will get the giraffe, the anteater or a fish from very deep water. Over text he will send pictures to prove it, and you should send worse ones back.
Any animal can be your loyal sidekick, but it comes with you everywhere, including work and the grocery store. Which one?
Why ask it
The condition is what turns a favorite animal question into a logistics problem. Somebody who says bear has not pictured the checkout line, so picture it for him.
What do you think a dog believes you do all day after you walk out the door?
Why ask it
There is no right answer and he will have one anyway: hunting, sitting in the car, standing on the other side of the door. A guy with a dog will answer for his own, and a guy without one can answer for a cat, which comes out funnier and colder.
Which sea creature are you least okay with existing?
Why ask it
Deep water makes a lot of people uneasy, and he will have a particular animal in mind, often one with too many arms or a light on its head. Ask whether he would rather meet it in the ocean or find it in his bathtub.
If your pet, or any animal you know well, could say one sentence to you, what would it be?
Why ask it
People mostly expect a complaint: about dinner time, the vacuum or the vet. The sentence he invents says a good deal about how he treats the animal, and the voice he does it in is a bonus.
Habits and brain
What's a weird habit of yours that you think nobody has noticed?
Why ask it
He will pause, because he has to decide whether to hand it over: tapping the door frame on the way out, eating breakfast standing in the same spot. Trade one of yours right away so it feels like a swap and not an inspection.
Do you have any superstitions, even ones you know make no sense?
Why ask it
He will open with 'not really' and then remember the game-day shirt, the seat he has to take, or knocking on wood and checking it was really wood. Get the story of the one time he skipped it and what he still blames on that.
Do you talk to things that can't answer, like your car, the printer or a houseplant?
Why ask it
Plenty of people do, and the tone is what to ask about: coaxing the car up a hill is a different person from threatening the printer. A guy who names his objects will tell you the names if you look interested.
Do you have a dream that keeps coming back?
Why ask it
A dream that repeats is weirder and shorter than a one-off, since he has had time to boil it down. Ask for the thirty-second version, and whether he has ever managed to change the ending.
Can you do anything strange with your body, like wiggle your ears, bend a thumb back or touch your nose with your tongue?
Why ask it
Best asked in person, because he will try all three before answering. If he has a real party trick he has been waiting for an audience, and you should have something of your own to show back.
What smell do you love that nobody would ever put in a candle?
Why ask it
A freshly opened can of tennis balls, a hardware store, a parking garage after rain. People are loyal to theirs, so say yours too and see whether either of you can stand the other's.
Does the volume have to land on an even number, a multiple of five, or do you not care at all?
Why ask it
A guy with a rule here has more of them, for the thermostat, the microwave timer and the gas pump. A guy with none will be baffled that this is a thing, and watching him find out is the entertainment.
What texture can't you stand to touch?
Why ask it
He will shudder while describing it, and the shudder is the answer. Velvet, chalk, wet paper and peach fuzz all have their enemies, and whichever is his, it is kinder not to test him with the real thing afterward.
What harmless thing gives you the creeps for no reason you can explain?
Why ask it
This is the small unease, not the phobia: mannequins, a row of old dolls, an empty parking lot at noon. Tell him yours before you laugh at his, and if it turns out to be a real fear, drop the jokes and move on.
What's the best shower thought you've ever had?
Why ask it
You are asking for the idea that felt like genius under hot water and fell apart on the towel. If he says he does not get them, ask what he does think about in there, which is usually an argument he is winning.
When you can't sleep, what does your brain decide to think about?
Why ask it
The funny answers are a comment he made six years ago or how an elevator knows which floor to stop at. Now and then this one turns serious, and when it does, leave the bit alone and listen.
Which hiccup cure do you swear by?
Why ask it
People inherit these like recipes: water from the far side of the glass, a held breath, a spoonful of something. He will insist his works, you will insist yours does, and neither of you needs to be right.
What do you do the 'wrong' way and refuse to change?
Why ask it
Somebody has tried to correct him, probably for years, and that person is the story: the teacher who gave up on his pen grip, the brother who still objects to the two-loop shoelaces. He will demonstrate if you look doubtful.
What's the strangest thing you've done while half asleep?
Why ask it
There is usually a witness, and the witness tells it better, so find out who saw it. Answering the phone with a line from the dream and getting fully dressed for school on a Saturday are the kind of thing to hope for.
What's the weirdest thing you find attractive that has nothing to do with looks?
Why ask it
The good answers are oddly exact: parking in one try, reading the instructions first, being nice to the bus driver. It leans toward flirting, so keep it for a guy you already tease a little, and do not fish for whether you qualify.
What if
Which three people you know are on your zombie team, and what is each one's job?
Why ask it
He has to rate his friends and family out loud, and the one he picks for cooking over fighting would be hurt to hear it. Ask who he would refuse to take and why, then whether you made the list.
You've been bitten by a zombie and nobody in your group saw it. Do you tell them?
Why ask it
In the movies somebody always hides the bite, and everyone watching groans. He will say he would own up, so find out how long he would wait first, and whether he would want the truth from you if it were your arm.
You're stuck on a desert island with three things, and none of them can be a boat or a phone. What do you bring?
Why ask it
Banning the boat is what makes him think, and the list gives him away: a knife, a pot and rope is one sort of guy, a hammock and a speaker is another. Offer to swap out one item and let him argue for it.
Everyone else on Earth disappears for twenty-four hours and then comes back. What do you do with the day?
Why ask it
Because they come back, it stays cheerful, and the plans are things like walking down the middle of the highway or trying every seat in a stadium. The follow-up is what he would leave behind so people knew he had been there.
Which superpower would be a letdown once you actually had it?
Why ask it
He gets to ruin a classic: flying is cold and full of bugs, mind reading is mostly other people's grocery lists. Then have him name a power too small to disappoint, like always knowing where his keys are.
You can travel back in time once, but only to tell one caveman one thing. What do you say?
Why ask it
He will start with something useful, realize he cannot explain how to make it, and settle for 'boil the water' or a joke. Play the caveman and keep asking 'why?' until his explanation runs out.
Would you get along with an exact clone of yourself, or would one of you move out within a week?
Why ask it
It is a sideways way of asking what he is like to live with, and he tends to answer honestly because he is only insulting himself. Which habit would annoy the clone first is the follow-up.
Aliens land and ask you for one object that explains humans. What do you hand over?
Why ask it
A TV remote, a fork, a participation trophy: the object is his whole opinion of people in one go. Ask what the aliens would wrongly conclude from it.
You've been shrunk to the size of a thumb in your own bedroom. What's the biggest threat?
Why ask it
He has to tour his own room from the floor, and the answer is usually the cat, the vacuum or a sock pile he would never climb out of. Next, how does he get to the kitchen?
Would you rather have fingers as long as your legs or legs as short as your fingers?
Why ask it
He will hold up a hand and study it, and may try to act out the walk. Long fingers look like the easy win until you bring up gloves, door handles and typing.
Would you rather always feel a sneeze coming that never arrives or have one popcorn shell stuck in your teeth forever?
Why ask it
Both are tiny and both would wear a person down, which is why he will take longer over this than over anything about superpowers. Whichever he picks, describe the other one as the obvious choice.
Which animal are you riding into battle, and what is it wearing?
Why ask it
A horse is not an answer, so send him back for a moose, an ostrich or a very large goat. The outfit matters as much as the animal, and a guy who gives his ostrich a tiny helmet is having a good time.
If you were a supervillain with a very small budget, what would your evil scheme be?
Why ask it
The small budget rules out lasers and leaves pettiness: every shopping cart gets one bad wheel, every pen runs dry on the last signature. Ask for the villain name and the catchphrase, in that order.
A genie grants three wishes but twists each one as literally as it can. How do you word the first?
Why ask it
This is for a guy who likes loopholes, and you play the genie. Wreck each wording in a new way, 'you never said the money would be yours to keep', until he is dictating a contract.
You have to vanish and start over in a small town. What's your new name, and what job do you tell people you do?
Why ask it
He will choose the name fast and with suspicious ease. The best versions come with a backstory that has one hole in it, so ask what slip would blow his cover, and try calling him by the new name for the rest of the day.
A door shows up in your home that wasn't there yesterday. Do you open it?
Why ask it
One kind of guy has it open before you finish the sentence, and the other wants to knock first. Either way he decides what is behind it, and the better follow-up is who he texts before going in.
The two of us
Would you still like me if I turned into a worm overnight?
Why ask it
It gets asked a lot online, and there is a right answer: yes, followed by details about the jar, the dirt and the little hat. It is flirting dressed as nonsense, so save it for a guy who already knows your humor.
If I called in the middle of the night and said 'bring a ladder and a jar of peanut butter, no questions', would you come?
Why ask it
The winning reply is a question about the peanut butter: crunchy or smooth. A guy who wants to know what the ladder is for has missed the bit but would probably still show up, which counts for something. It only works if he knows you well enough to believe you might call.
If we swapped phones for an hour, what on yours would confuse me the most?
Why ask it
An app he cannot justify, forty alarms, a notes page that says only 'the owl knows'. It is an offer to explain himself, not a request to look, so do not reach for the phone.
Which animal am I? You can't pick one just for being cute.
Why ask it
Banning cute forces him to think about how you actually behave, and you may get an otter, a heron or a very determined goat. Make him give a reason, then tell him which one he is.
If someone made a nature documentary about the two of us, what would the narrator whisper?
Why ask it
He has to describe how you are together from the outside, in a hushed voice, and it nearly always comes out fond. It needs a little history between you, so keep it until you have had a few real conversations.
Which of us would last longer in a haunted house, and what sends the other one running?
Why ask it
He will say himself, so ask what exact noise would break him. If you have ever seen him jump at anything, now is the time to mention it.
What do you think I'd be strangely good at after the world ended?
Why ask it
An odd question with a compliment buried in it, since he has to name something you can do: bargaining, finding food, keeping people calm. Give him his job in return and compare it with the one he would have chosen.
What's the strangest thing you've noticed about how I text?
Why ask it
Most people have a tic they cannot see: the one thought sent as five messages, the period that sounds angry, the 'haha' that means nothing. Take it well, because he will ask for his next.
If we were stuck in an elevator for six hours, what would we be arguing about by hour four?
Why ask it
He needs to know you a bit to answer, and the guess shows what he thinks you two are like: the escape plan, a movie, who used up the phone battery. Start the argument now and save time.
If I were a haunted object in your house, which object would I be?
Why ask it
Strange enough that he has no stock answer, so what he says is fresh: a lamp that comes on when he is sad, a kettle that boils when he lies. With a guy who does not know your nonsense yet it will only confuse him.
What would go in a museum exhibit about the two of us?
Why ask it
A receipt, a screenshot, a jacket one of you borrowed and kept. It takes shared history, and what he lists tells you which moments he held on to, so have him write the little card that goes beside each item.
Over text
Draw a horse in under a minute and send it to me.
Why ask it
Horses are hard to draw, so the result is funny whether he can draw or not. Send your own before you see his, and keep both, because they will come up again.
Using only emojis, tell me what you did today and I'll guess.
Why ask it
It takes him ten seconds to send and can take you ten minutes to solve, which is a good trade. Guess wrong on purpose once or twice, since his corrections are funnier than the right answer.
Describe where you are right now as if it were a crime scene.
Why ask it
A desk becomes 'signs of a struggle near the keyboard, one cold coffee, no witnesses'. A dry guy does this best, and if he gets into it, ask who the suspect is.
Wrong answers only: what is a giraffe?
Why ask it
The format does the work, so a guy who claims he is not funny still sends something good. Reply with a wrong answer of your own, then swap the giraffe for a stapler or the moon.
What's the last thing you looked up at 2 a.m. that had nothing to do with anything?
Why ask it
How tall a certain actor is, whether a shark can swim backward, what became of a band from school. He can check his history for the honest answer, and you should have yours ready when he asks.
Send me one true fact and one made-up one, and I'll guess which is which.
Why ask it
A guy who is good at this picks a true fact that sounds fake, and you will get it wrong. Keep score over a few days, and take your own turn so he has to guess too.
It's 3 a.m. and something in your kitchen makes a noise. List what you think it is, most likely first.
Why ask it
The list gets less sensible as it goes: the fridge, the cat, a raccoon, his own past choices. Ask at which item he would actually get out of bed.
Pick a number from 1 to 10 and don't ask why.
Why ask it
Decide what the number means before you send it: how many questions he now owes you, or which question in this group he gets next. Not knowing is what makes him answer, so do not explain until he has picked.
Write me a two-sentence horror story about something boring, like laundry.
Why ask it
Two sentences is short enough that he will try, and a boring subject makes it silly, not scary. 'The dryer stopped. I had not turned it on.' is the standard to beat.
Send a voice note of what you think a dinosaur really sounded like.
Why ask it
Nobody can prove him wrong, which frees him up. A guy who sends it without negotiating is comfortable looking ridiculous, and you owe him one back, so choose your dinosaur.
Finish this sentence badly: 'The secret ingredient is...'
Why ask it
It fits in a single reply and has no right answer: regret, more butter, a second smaller sandwich. Follow with another opening, 'Nobody expected the dentist to...', and take turns writing them.
What question do you wish someone would ask you because you already have a weird answer ready?
Why ask it
Some guys have been sitting on a theory for years and only need the door opened. If he has one, ask it back to him word for word and let him go.
How to ask a weird question and keep the bit going
Practical guidance for the conversation itself
Making one weird question last
Ask for the plan, not only the pick
Choosing takes him one second and ends the question. 'How, exactly?' and 'then what?' are the two follow-ups that work under almost everything on this page: how he gets the bear through the checkout line, what he does after the first wish goes wrong.
Change one thing at a time
When he answers too fast, add a single condition. The duck fight moves to flip-flops, the hot dog ruling gets tested on a sub roll, the battle animal needs an outfit. One change per answer keeps him defending the plan. Three at once looks like you are moving the goalposts, and he will stop building.
Rule out the answer he has given before
Several questions here ban the easy answer, in the wording or in the note: no boat on the island, no horse in the battle, no animal picked for being cute. Do the same to any question he has heard already. A superpower question that forbids flying gets a new answer from a guy who has been saying flying since fourth grade.
Take the side he left empty
If he says a Pop-Tart is not ravioli, become its lawyer. A weird question lasts as long as it has two sides, so argue the one he did not pick even when you privately agree with him. Concede when he lands a point you cannot answer: a ruling you both accept is a better ending than a draw.
Bring a good answer back later
His pointless law, his small-town alias and the horse he drew are worth more the second time. Point it out when he breaks his own law, or use the alias in a text next week. A weird answer that becomes a running joke between you has done more than the question did.
Where to start, by how well you know him
You hardly know him yet
Stay in Warm-ups and Food and animals. Nothing there asks for more than an opinion or a childhood story, so the worst outcome is a strong ruling about hot dogs, and you find out quickly whether he enjoys this kind of question at all.
You have talked a few times
Habits and brain is the next step, because those answers are true things about him and not inventions. Offer one of your own for each one you ask for. A habit or a superstition handed over one way feels like being studied.
You have time to fill
What if is for a long drive, a slow line or a late call. Each scenario can run ten minutes when you keep adding conditions, so one or two will do. The zombie ones go furthest with a guy who watches that kind of movie and has already cast himself in it.
He already gets your humor
The two of us only works once he knows you are teasing. To someone you met last week, the worm question reads as a test with a hidden right answer. To a guy who knows you, it is an invitation to say something nice in a ridiculous way.
Weird questions to ask a guy over text
Show him it is a bit
With no face attached, a strange question can look like a message sent to the wrong person. Put 'I need a ruling on something' or 'urgent and stupid question' in front of it so he knows what kind of reply is wanted.
Pick by the reply it needs
A ruling fits in one message: the hot dog, the Pop-Tart, the number the volume has to land on. A list gives him something to build, like the kitchen noise at 3 a.m. or the gas station dinner. A demonstration does not travel, so keep the ear wiggle and the bent thumb for a day you are in the same room.
Ask for evidence
A photo of the thing in his room, the horse drawing, a voice note of the dinosaur. A picture or a recording breaks up a wall of typed answers and gives you something to tease him about for weeks.
Play your part in the reply
The genie and the caveman need you in character. Answer as the genie twisting his wish, or as a caveman who has never heard the word 'germs', and hold it for three or four messages. Typing makes that easier than doing it face to face, because nobody can see you laughing.
When weird stops being fun
Strange, not personal
The questions here are odd about ducks, potatoes and ghosts. None is odd about his looks, his exes or his body, and a question that only makes someone uncomfortable is not a weird question. That holds for answers too: if he steers a what-if somewhere crude, skip the laugh and go back to the clone or the caveman as if nothing was said.
The two of us is a game, not an exam
The worm question and the midnight ladder have fond answers available, but they are jokes and he may joke back. If he says he would put worm-you out in the garden, that is him playing along. Sulking over it turns the list into a quiz he can fail, and he will start giving the careful answer in place of the funny one.
Creepy is only fun when he chose it
The ghost, the kitchen noise at 3 a.m. and the sea creature are meant to be silly. Now and then one lands on something that truly frightens him, deep water or dolls, say. Treat that as something to remember: no picture of the fish, and no bringing it up later in the dark for a laugh.
When he asks why you want to know
Some guys hear a weird question as a trap and answer 'I don't know, why?'. Give your own answer first, in full, so he can see there is nothing behind it. If the scenarios keep getting shrugs, switch to Habits and brain, or the other way around: inventing a zombie plan and admitting a superstition are different kinds of fun, and not everyone is in the mood for both.