Unhinged Questions to Ask Your Boyfriend
Unhinged questions for a boyfriend who will commit to a bit: the weird questions to ask your boyfriend when a normal one would only get a normal answer, and the ridiculous ones that start a twenty minute argument about pigeons. The 57 questions run in the order an evening goes, in five groups: Warm-ups, Petty, Weird but true, Full bit and The two of us. The quick silly ones come first, and the ones that need him to build something, or to say whether he would still love you as a worm, come once he is playing along.
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The questions
Each question, and why to ask it
Warm-ups
You have to fight one animal every day for the rest of your life. Which animal do you pick?
Why ask it
He will answer on instinct and then have to defend it, which is where the twenty minutes go. A hen every morning sounds easy until he counts the mornings, so push on the math: that is one fight a day for fifty years, and the hen is learning.
Would you rather be permanently slightly damp, or permanently hear a faint kazoo?
Why ask it
Two mild horrors and no right answer. If he wants to know how loud the kazoo is and whether it plays a tune before he commits, answer him seriously, because negotiating the terms is the game.
You wake up as a kitchen appliance. Which one, and who in this house uses you first?
Why ask it
Picking the appliance takes a second. Wait for the other half, because being the coffee maker someone needs at six every morning is a different life from being the waffle iron nobody has touched since the day it was bought.
Which vegetable looks like it's hiding something?
Why ask it
Nobody arrives with an answer to this, so you get to watch him consider vegetables one at a time with real suspicion. Whatever he names, an artichoke or a suspiciously clean leek, ask what he thinks it did.
How many pigeons would it take to lift you off the ground, and would you let them?
Why ask it
He will start doing real arithmetic about pigeon lifting power within ten seconds, which is the fun of it. The second half matters more than the number: a man who says yes at once has already pictured where they are taking him.
You have to replace your name with a sound. What sound?
Why ask it
The only thing at stake is whether he will make the sound out loud, and he will want you to go first. Use it for the rest of the evening whenever you need his attention.
What would your wrestling name be, and what's your finishing move called?
Why ask it
A two second answer for anyone who watched wrestling as a kid and a real struggle for everyone else, and both are funny. Make him announce himself in the voice, then tell him the name you would have given him.
You can only whisper or shout for the rest of the week. Which, and where does it go wrong first?
Why ask it
The choice is easy and the consequences are the question. Walk him through his actual week: the Monday meeting, the phone call to his mom, ordering a coffee.
Which piece of furniture in this room has the worst personality?
Why ask it
Works anywhere because the answer is sitting in front of him. Once he has picked the smug armchair, ask what it says about the two of you when you leave the room.
You get a tail, but you have to choose which animal's. Whose?
Why ask it
A monkey's tail is the practical pick because it is an extra hand, and a fox's is pure vanity, so the choice sorts him quickly. The better follow up is what he plans to do about pants.
Would you rather sneeze glitter or hiccup in a different stranger's voice every time?
Why ask it
One is a cleaning problem and the other is a social one, and which he dreads more is the real answer. If he picks glitter, remind him how long allergy season lasts.
What would you name a goldfish if you wanted people to be afraid of it?
Why ask it
A naming question with a job to do, which gets better answers than asking for a funny pet name. Titles help, so if he stalls, suggest he start with a military rank or a 'the'.
What's a normal word that starts sounding fake if you say it five times?
Why ask it
He has to test candidates out loud, so within a minute he is sitting there repeating 'spoon' at you. That is the whole game, and it suits a waiting room or a car.
Petty
You're legally required to have a nemesis. Who is it and what did they do to you?
Why ask it
Gets the pettiest live grievance out of him under cover of a joke. What comes out is usually a real person from work or a neighbor with a leaf blower, and you will learn something you would not have got by asking what is annoying him.
What's the pettiest thing you've ever held a grudge about?
Why ask it
Ask how long he has held it and whether the other person knows, because the best ones are years old and entirely one sided. It only works if he can tell it against himself, so offer your own pettiest one in the same spirit.
Which species of animal has personally wronged you, and what happened?
Why ask it
A grudge with nobody on the other end, so he can be as furious as he likes at a seagull. There is usually a real incident behind it, with a stolen ice cream and a beach he can still name.
Which machine or object did you last lose an argument to?
Why ask it
A self checkout, a printer, a duvet cover: he has raised his voice at one of them this month. Ask him to do both sides of the conversation, his and the machine's.
What's the dumbest hill you'd still die on tonight?
Why ask it
This one is about an opinion, not a person: the correct way to load a dishwasher, a film everyone else is wrong about. Take the other side whether you believe it or not, because he wants an opponent more than he wants agreement.
You can delete one food from existence. What goes, and who's going to be furious?
Why ask it
Naming the food is a preference, and naming the furious person is a story. When it turns out his dad would never forgive the loss of raisins, ask how the next family dinner goes.
What word or phrase would you ban everyone from saying, starting tomorrow?
Why ask it
Aimed at how people talk, which he has stronger feelings about than he knows. He will do the voice of whoever says it most, often someone from work, and you get the impression for free.
You get to issue one fine, any amount, for something that isn't illegal. What's the offense?
Why ask it
The size of the fine tells you how long he has been thinking about it. If he needs a start, offer stopping dead at the top of an escalator or playing a video out loud on a train, and ask where the money goes.
What's the smallest thing that has ever ruined an entire day for you?
Why ask it
A true one, and funnier for it: a snapped shoelace, a sock that got wet at eight in the morning. Do not point out that it was small, because he knows, and that is why he is telling it.
If you could send one strongly worded letter to any person or company with no consequences, who gets it?
Why ask it
Ask for the opening line and the sign off, since 'yours in disappointment' is where the joke lives. If the letter turns out to be for someone who really hurt him, drop the bit and listen.
Weird but true
What's the weirdest thing you do when you're home alone that you'd deny under oath?
Why ask it
Nobody offers this one cold, so go first with yours: the commentary you give while doing the dishes, the bow you take after parking well. Promise it stays in the room and mean it.
What's in your search history that you would defend in court?
Why ask it
Sharper than asking what he has searched, because it asks for the one he is proud of rather than the one he is embarrassed by. The best answers are long investigations into something completely pointless.
What completely made-up scenario have you rehearsed in your head more than once?
Why ask it
The award speech, the talk show interview, the calm reply to an argument that never happened. He has one and has probably never been asked, so offer yours first and be specific about it.
What rule do you follow that nobody ever gave you?
Why ask it
He may need a minute to notice it is a rule at all, so tell him one of yours while he thinks. Even steps on a staircase and never taking the first parking space both count, and the good part is asking what he thinks happens if he breaks it.
What did you get obsessed with for about two weeks and then never touch again?
Why ask it
There is usually equipment involved, and it is usually still in a cupboard. Ask what it cost and whether the sourdough starter, the chess app or the harmonica is ever coming back.
What ordinary thing would you be world class at if anyone held a tournament?
Why ask it
This is a brag he has been holding in for years, whether it is packing a car trunk or carrying all the groceries in one trip. Nodding is not enough: demand a demonstration this week.
What's the strangest thing you've ever been seriously competitive about?
Why ask it
You are after the time it got out of hand and the name of the opponent. A board game from years ago or a step count against his brother will have more heat in it than anything about his job, so ask whether a rematch is pending.
What noise do you make around the house that you've never heard another person make?
Why ask it
He will deny having one and then make it by accident before the night is over. If you already know what it is, do it back to him and watch him recognize it.
What's a conspiracy theory you don't believe but respect the craft of?
Why ask it
The phrasing lets him praise the construction without endorsing anything, which is the difference between this and a conversation you do not want to have. If he starts actually defending one, change the subject rather than arguing at eleven at night.
If you had to give a forty minute talk with no notes, starting now, what's it on?
Why ask it
The honest answer is whatever he knows far too much about, whether that is one football season or how bridges stay up. Ask for the first three minutes on the spot, and be ready to stop him at ten.
What's something you find genuinely funny that nobody else seems to?
Why ask it
A sincere question dressed as a silly one. A joke that has never landed with anyone is a real thing to hand over, so do not fake the laugh: if you do not get it either, ask him to explain why it is funny, which he will enjoy more.
Full bit
You get one superpower, but it only works while you're standing in a supermarket. What do you take?
Why ask it
Flying is no use under strip lighting, so the obvious powers fall away and he has to think about what a supermarket actually demands. Hope for something small, like always choosing the fastest checkout line, and ask what he does with it on a Saturday.
You have to be haunted. What should the ghost be obsessed with?
Why ask it
The best ghosts have one narrow complaint: a ghost who only cares about coasters, or one who sighs every time he checks his phone. If he shrugs, offer him those two and let him choose between them or beat them.
If a documentary crew followed you for a week, what would the episode be called?
Why ask it
The title is how he thinks his week looks from the outside, and you are allowed to disagree. Offer your own title for the same footage, then ask who he wants narrating.
A museum about your life opens, but the only part that's finished is the gift shop. What's for sale?
Why ask it
The gift shop makes him turn his own habits into merchandise: the mug, the T-shirt with his catchphrase on it, the overpriced replica of his worst jacket. Ask what the bestseller is and what ends up in the bargain bin.
The pilot has passed out and a voice on the radio is talking you through it. Do you land the plane?
Why ask it
Ask for his confidence as a percentage before anything else. Then ask which control he touches first and what he says to the passengers, and watch the percentage come down one question at a time.
You're in charge of a small country for one week. What's your first law?
Why ask it
A week is too short to fix anything, so the right answer is small and selfish, like banning one particular song from every shop. If he starts on tax policy, remind him he only has until Sunday.
You're founding a secret society devoted to something completely harmless. What's it for, and what's the handshake?
Why ask it
Good versions of this have ranks, a meeting place and one forbidden snack, so keep asking for one more detail. He has to perform the handshake on you, which is the only reason the second half is there.
Aliens land and you have ten minutes, plus whatever is in this room, to convince them you run Earth. What do you do?
Why ask it
The room limit is what stops this being a speech. Watch which objects he reaches for, and play the unimpressed alien who keeps asking to see his supervisor.
You're turned into a bird for one day and may mildly inconvenience one person. Which bird, and who?
Why ask it
Two choices that pull against each other, since the impressive birds are bad at small revenge. An eagle cannot do 'mildly', which is why a pigeon is the considered answer. Ask what exactly the inconvenience is and how many times he goes back.
You're hosting a cooking show tonight using only what's in your kitchen right now. What's the episode?
Why ask it
Funniest when the cupboards are close to empty and he has to sell half a jar of pesto and some crackers as a concept. Ask for the show's title and the line he says to camera at the end.
You have to fake your own death. What's the plan, and where do you turn up two years later?
Why ask it
Let him build the whole plan, down to the new name and what he does for money. Where he turns up two years later is the honest part, because it is usually where he would live if nothing was keeping him.
The two of us
Would you still love me if I was a worm?
Why ask it
The one he may already have been asked, and there is still no safe answer. A yes is only the start: ask where the worm lives, whether it comes on vacation, and how he introduces it to his mother.
If I turned into a houseplant overnight, where would you put me and how often would I get watered?
Why ask it
A gentler cousin of the worm question, with logistics. An honest answer about forgetting to water you is funnier and kinder than a promise of perfect care, so let him be honest.
What would my villain origin story be?
Why ask it
He has to name the small thing that would finally tip you over, which means he has been paying attention. Expect something like the day a cafe took your usual order off the menu, and expect it to be accurate.
If I were a cryptid, where would people report seeing me and what would I be doing?
Why ask it
A sighting needs a place, a time of night and a blurry activity, and he knows all three for you. 'Spotted near the fridge at 1 a.m., holding cheese' is the kind of answer to hope for.
A perfect copy of me turns up at the door and we both swear we're the real one. What one question do you ask?
Why ask it
His question shows what he thinks only you would know: an in-joke, your order at one particular place, what you said on the second date. If he says he would leave the two of you to sort it out between yourselves, that counts as an answer too.
What false fact about me could you get a stranger to believe?
Why ask it
A good lie has to sit close to the truth, so what he invents shows how he would describe you. Former junior chess champion and banned from a zoo are very different readings of the same person.
If we were a crime-fighting duo, what are our names and which of us is the sidekick?
Why ask it
The sidekick clause is where the negotiation starts, and neither of you should give in quickly. Settle it by listing each other's powers, which have to be things you can really do.
Which of us would crack first as a medieval peasant, and over what?
Why ask it
He will say you, you will say him, and both cases get made with evidence from your last camping trip or power outage. Rule out coffee and phone chargers so he has to find a less obvious breaking point.
What would the warning label on me say?
Why ask it
Short enough to answer in one line and personal enough that he will think before he does. Write his in return, and keep both light: a label says 'may narrate films', and a real complaint belongs in a different conversation.
What's the weirdest thing about me that you've decided you like?
Why ask it
It sounds like a trap and is the opposite of one. Take the answer as the compliment it is, and do not argue with it or ask for a second one.
What's the dumbest thing I could actually talk you into this weekend?
Why ask it
Puts a real plan on the table, which the invented scenarios never do. If the answer is a matching outfit or a four hour drive for one specific sandwich, you now have something to book.
Which of these questions did you think was the stupidest, and what should I have asked instead?
Why ask it
Hands him the last word and usually produces a better question than the ones on this list. It also tells you whether he was enjoying it or being a good sport, which is useful to know before the next round.
How to Make Absurd Questions Land
Practical guidance for the conversation itself
How to Ask Them
Deliver it completely straight
The animal fight question is funny because it is asked as though it were a practical scheduling problem. Laughing before he answers tells him nothing is at stake, and he will match your effort level exactly.
Stay inside the premise
When he picks an animal, ask about the venue, the weather and whether he gets a weapon. Following up inside the joke is what turns a one line answer into the actual conversation, and stepping outside it to say that would never happen ends everything.
Give him multiple choice when he stalls
Some people cannot generate absurdity from nothing but are excellent at judging it. Offer two ridiculous options and he will usually reject both and produce a third, which is what you wanted.
Answer everything you ask
These only work as a trade. A round where one person asks every question and answers none is an interview with a strange theme, and he will notice by the third pigeon.
Do not explain what the answer means
Telling him his appliance choice reveals something about his childhood is the fastest way to end the game. Ask another question instead.
Which Group to Open With
He is tired, or half watching something
Stay in Warm-ups. The kazoo, the tail and the goldfish can each be answered in a word, and a word is all you are asking for. If one of them gets a full sentence and a counter question, he is in, and you can move down the page.
Something annoyed him today
Go straight to Petty. The nemesis, the fine and the strongly worded letter give a bad mood somewhere ridiculous to go, and he gets to be unreasonable on purpose. Agree with every verdict he hands down, however harsh on the self checkout.
You want the weird questions that tell you something
Weird but true holds the weird questions to ask your boyfriend when you would like a real fact back: the rehearsed scenario, the private rule, the two week obsession. Nothing there is invented, so trade one of your own for each one he gives up.
You have a long drive or a slow dinner
Full bit is built for time. One scenario, the gift shop or the secret society, can fill ten minutes if you keep asking for the next detail, so pick two and let them run. Do not rush to a third because the first one went well.
He is already laughing
The two of us comes last for a reason. Ridiculous questions to ask your boyfriend about yourself only land once he knows you are after a joke and not a compliment. Asked cold, the worm and the warning label sound like tests with a wrong answer.
Three Runs That Build Well
The escalation
- 1Start with the animal you fight every day and let the argument about the weight class run all the way out.
- 2Move to the supermarket superpower, which needs the same kind of thinking but rewards more specific answers.
- 3Land on faking your own death, which is where someone who is warmed up will build a plan with a wig in it.
The petty run
- 1Open with the legally required nemesis, because it is nonsense with a real person hiding in it.
- 2Follow with the pettiest grudge, which will confirm the nemesis was not a joke at all.
- 3End on the dumb hill he would die on tonight, and then actually have the argument.
The about-you run
- 1Open with the worm, and make him settle where it lives before you accept the yes.
- 2Move to the cryptid sighting, which lets him describe your habits without it sounding like a complaint.
- 3Finish on the weirdest thing about you he has decided he likes, and take the answer without arguing.
Ways This Falls Flat
- Reading them off your phone in order. Pick three before you start and put the screen down, because a question read aloud from a list sounds like a quiz he did not sign up for.
- Asking in a group when he is the only one being asked. Absurd answers need everyone equally exposed, or one person is just performing while the others watch.
- Sending the long ones by text. The Full bit questions depend on speed and on hearing him commit, and an answer typed, reconsidered and trimmed before sending has lost the best part. The kazoo survives a text and the secret society does not.
- Starting on Full bit when he is worn out. Those need him to build something, and a tired person gives one word and feels he has failed. Use the short ones, or Petty if it was the day that wore him out.
- Reaching for the serious version underneath. There is a real question under most of these, and going after it directly halfway through is how a good evening turns into a different conversation neither of you planned.