Weird Questions to Ask a Girl
For anyone who wants to make a girl laugh without asking the same five things everyone else asks. These 84 weird questions are odd on purpose and never creepy, sorted from safest to boldest: openers for someone you barely know, absurd what-ifs, food and animals, odd habits and quirks, dreams and childhood strangeness, and a last group about the two of you for when she already gets your humor. The notes are about delivery: how to ask with a straight face, the kind of answer to hope for and which questions to hold until she knows you.
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The questions
Each question, and why to ask it
Openers
What is the weirdest thing about you that you are secretly proud of?
Why ask it
Ask it with a grin and offer yours first, because 'weird' sounds like an accusation until you have confessed to something. A good answer is small and specific, like being able to name any dog breed from a block away. Whatever she says, treat it as a point in her favor.
What is the strangest object in your room right now, and how did it get there?
Why ask it
The second half is where the story is: a road sign, a jar of buttons, a trophy for a sport she never played. By text, a picture of the object alone is a fair thing to request, as long as your own strangest goes back in return.
What talent do you have that has never once been useful?
Why ask it
Expect something like balancing a spoon on her nose or naming a song from its first note. If she can show you on the spot, let her, and be more impressed than the talent deserves.
What is the weirdest rabbit hole you have gone down online when you should have been asleep?
Why ask it
Rabbit holes are harmless and strange: the history of a cereal mascot, whether crabs get bored, one lighthouse keeper's entire life. Share one of yours first and never ask to see her phone. If she laughs and says she cannot tell you, let that be the answer.
Which perfectly ordinary object do you find slightly unsettling?
Why ask it
Mannequins, wet wooden spoons, a balloon that has sunk to the floor. Do not try to talk her out of it. Ask when she first noticed, then admit to one of your own so she is not alone in it.
What is the strangest fact you know that sounds like you made it up?
Why ask it
Trade facts one for one, and hold off checking hers on your phone while she is still telling it, since being believed is half the pleasure. 'A group of flamingos is called a flamboyance' is the level to aim for. If hers turns out to be wrong, that is your reason to message her tomorrow.
What is the strangest compliment you would honestly love to get?
Why ask it
This swaps the usual line about her eyes for one she gets to design: 'you have the handwriting of a villain', 'you would be good in a blackout'. Remember the answer, because paying her that exact compliment a week later is the whole reward.
What is the weirdest nickname anyone has ever given you, and did it stick?
Why ask it
Nicknames nearly always come with an origin story, usually involving a sibling or a team. Ask before you use it yourself, since some are only allowed from the person who invented them.
What word do you think is far funnier than it has any right to be?
Why ask it
Say yours out loud first, slowly, so she can hear why: 'spatula', 'pamphlet', 'gazebo'. It takes ten seconds to answer, which makes it right for the first minutes of talking to someone.
What is the weirdest thing you have watched a stranger do and quietly respected?
Why ask it
The word 'respected' keeps it kind: think of someone eating a whole rotisserie chicken on a train, or a man carrying a cat in a backpack with a window. If her story turns into making fun of the person, steer back to what she admired.
What rule did your family have that you assumed every family had?
Why ask it
She probably found out at a friend's house, so the moment she realized is the real story: no whistling indoors, shoes lined up by size, a chair nobody was allowed to sit in. It is strange without being personal, which suits the first week of talking to someone.
What is the oddest thing you have ever collected?
Why ask it
Kid collections are the best ones: erasers shaped like food, bottle caps, the stickers off fruit. Find out whether hers survives and where it lives now. If she never collected anything, what would she start with tomorrow?
Which emoji do you not trust, and what do you think it is hiding?
Why ask it
Built for texting, since she can send the suspect as her answer. The upside-down smile and the moon with a face are frequent suspects. Use only that emoji in your next message and see if she plays along.
What if
If you woke up tomorrow as a pigeon, what is the first thing you would do?
Why ask it
It needs no setup, and the less you explain the better it lands. Listen for whether she goes practical (find bread) or petty (find one specific person's car). Then ask which statue she would claim as hers.
What nearly useless superpower would you still be thrilled to have?
Why ask it
The ordinary version of this gets 'flying' and stops there, so insist on useless: always picking the fastest line at the store, refolding a map on the first try, never stubbing a toe. Then invent the one situation in which hers saves everybody.
If you could walk through walls, but only one wall a day, which wall is today's?
Why ask it
The limit is what makes it a question, because one wall means choosing between the bakery after closing and the shortcut out of a dull class. Keep your own pick just as small and harmless.
If you had to be a piece of furniture for a day, which piece, and in whose house?
Why ask it
Deliver it deadpan, as if it were a normal thing to need to know. The house is the revealing part: her grandmother's armchair is a very different answer from a stool in a celebrity's kitchen.
If aliens landed and wanted a tour of your town, where would you take them first and what would you steer them away from?
Why ask it
Some people go grand, with the best view for miles, and some go straight to a drive-through. The places she would steer them away from make the funnier list, so hold out for that half.
If zombies showed up tonight, what in your home becomes the weapon and what becomes the snack supply?
Why ask it
The zombie question is an old favorite, so this version makes her look around the room she is in. A frying pan and a worrying amount of cereal is a typical inventory. Follow up by asking how many days she honestly gives herself.
If you had to swap your hands for two kitchen utensils, which two would you pick?
Why ask it
Whisk and tongs is a strong answer, and two spoons is a cry for help. Then there is the matter of sending a text, which is where every plan falls apart. It is odd enough to work better once she has already laughed at something else.
Would you rather have a tail you cannot control or ears that swivel toward anyone talking about you?
Why ask it
Both give her away, which is the joke: the tail wags when she is pleased and the ears catch her eavesdropping. Ask which would be worse on a first date, then pick the other one so you have something to argue about.
Would you rather cry lemonade or yawn soap bubbles?
Why ask it
Short enough to send as a text with nothing around it. A good answer comes with logistics, such as a sad movie or a long Monday meeting. If she picks in one word, ask who has to clean up.
Would you rather have knees that squeak like a dog toy or elbows that ring like a bicycle bell?
Why ask it
Have her walk through a normal day with her choice: a quiet library, a flight of stairs, a hug. The squeak is funnier and the bell is more useful in a crowd, so argue for whichever one she turns down.
If you shrank to the size of a grape for one afternoon, where would you go?
Why ask it
Answers split between adventure, like riding the cat, and comfort, like a nap in a slipper. Then find out what she would finally get a proper look at from down there: the inside of a vending machine, the gap behind the fridge.
If you were turned into a houseplant, who do you trust to remember to water you?
Why ask it
Under the silliness it asks who she relies on, and she will usually name a real person fast. Ask what kind of plant she is too. Volunteering yourself as the waterer is fine once you know her a little, and a bit much before that.
If your shadow quit and walked off, what would its resignation letter say?
Why ask it
Too strange for a first conversation, so keep it for someone who already sends odd things back to you. The best replies are in office language: 'effective immediately', 'due to the long hours and being stepped on'. Offer to write yours as well.
If you got to name a newly discovered planet, what would you call it and who would be banned from visiting?
Why ask it
Naming it after herself is a perfectly good answer. Spend longer on the ban list, and keep it to harmless offenders: people who clap when the plane lands, anyone who replies with just 'k'.
If you had to wear one costume every day for a year, which costume could you live in?
Why ask it
Practical people say astronaut or pajamas with feet, and brave people say a full mascot suit. Ask about the hard days: a job interview, the beach, a wedding. If she has a photo from a past Halloween, this is when it may come out.
Food and animals
What is the strangest thing you have eaten on purpose?
Why ask it
'On purpose' rules out the bug she swallowed on a bike and gets you a story with a decision in it: a dare, a trip, a grandparent's recipe. Ask whether she would eat it again. Never pull a face at food that turns out to be normal in her family.
What snack do you make for yourself that you would never serve to a guest?
Why ask it
The correct response to pickles wrapped in cheese or cold spaghetti in a tortilla is to request the recipe. Offering to try it is braver, and gives you a reason to see her again.
If you were a vegetable, which one would you be, and are you happy about it?
Why ask it
An old standby that still works if you ask it completely straight. Her reasons are what you want: a potato because she is good in any situation, an onion because she has made people cry. Have a guess at hers before she answers, and make it a flattering vegetable.
Which animal noise can you do well enough to fool the animal?
Why ask it
She will either refuse flat out or do it at full volume, and both tell you something. Go first with a bad one, a seagull or a tired cow, so the bar is on the floor. In a quiet restaurant, save it for the walk home.
Which animal would be the worst at keeping a secret?
Why ask it
Parrots have an unfair disadvantage. A fun reply names the animal and the secret it would spill, such as a dog telling everyone where the treats are hidden. Then find out which animal she would trust with hers.
If you could keep any animal as a pet with no danger and no mess, which strange one would you choose?
Why ask it
Taking away the danger gets you a capybara in the bathtub or an octopus that opens jars. Have her walk you through an ordinary evening at home with it. If she answers instantly, she has thought about this before, and you should find out for how long.
What food will you not eat purely because of how it feels in your mouth?
Why ask it
Texture opinions are strong and oddly specific: mushrooms, a banana with one soft spot, anything described as 'jellied'. Let her describe the horror in full. It is also useful to know if you ever cook for her or pick a restaurant.
What is the weirdest thing you have ever seen an animal do?
Why ask it
If she has a pet, this opens a long file of evidence, possibly with videos. Without one she may still have a crow that waited at the crosswalk or a goat on a roof. Give her time, because this is a story and not a quick answer.
What do you think a cat is looking at when it stares at an empty corner?
Why ask it
There is no right answer, so she has to invent a theory: a ghost, a draft, a long-running grudge against that wall. Build on hers instead of replacing it. Dog people can answer for the dog that barks at nothing.
Which food would make the worst pillow?
Why ask it
Pure nonsense, and it should arrive with no warning in the middle of an ordinary chat. Soup is clever, a pineapple is painful, lasagna is surprisingly tempting. Asking which food would make the best one buys you two more minutes.
If you could combine two animals into one, which two, and what is the new one called?
Why ask it
Hold out for the name, since a giraffe crossed with a hamster is only an idea until it is a giramster. What it eats and whether it could live in an apartment come next. If you are together, a napkin drawing of the result is worth the embarrassment.
What did you refuse to eat as a kid for a reason that made no sense?
Why ask it
The reasons are the treasure: peas because they were looking at her, bread crusts because a cousin said something about them. Ask whether she ever came around. Parents feature heavily in these stories, usually losing.
What is the oddest thing you have eaten for breakfast and felt fine about?
Why ask it
Cold pizza is too normal to count, so push for better: leftover curry, birthday cake, a handful of croutons. It makes a good morning text. Whatever she says, your position is that breakfast has no rules.
Do you think birds are ever afraid of heights?
Why ask it
A passing thought to send with no context at all. She might treat it as science or as tragedy, picturing one nervous pigeon who walks everywhere. Either way, ask which kind of bird she thinks it would be.
Habits and quirks
What habit of yours would you have to explain to a new roommate?
Why ask it
Putting it on a roommate makes the weird habit easier to admit: eating cereal standing up at midnight, saying goodbye to the house. Have yours ready. The right reaction is 'that makes sense', even when it does not.
What superstition do you follow even though you do not believe in it?
Why ask it
These are often handed down by one particular relative, so find out who gave her the knock on wood or the rule about umbrellas indoors. There is no point arguing the logic when she has already said she does not believe it.
Do you have a lucky object, number or pair of socks, and what has it supposedly done for you?
Why ask it
'Supposedly' gives her room to laugh at herself while still defending the socks. Ask for the record: the exam it passed, the game it won. If she has nothing lucky, she can tell you what she would choose if she were assigned one today.
What do you count without meaning to: stairs, ceiling tiles, steps between lampposts?
Why ask it
Either she says 'nothing, who does that' or she lights up because somebody finally asked. If it is the second, find out whether there is a number she likes to land on. Say what you count before she has to wonder whether it is only her.
When nobody is around, which is it: singing, winning an argument from three years ago or giving an acceptance speech?
Why ask it
Ask it like a survey and tick your own box first. If it is the argument, find out who she is finally beating. If it is the speech, she has to tell you what the award is for.
What object in your life has a name: a car, a plant, a laptop?
Why ask it
Named objects come with personalities, so ask what the car is like on a bad day. If nothing of hers has a name, offer to name something together on the spot. Asking after 'Gerald' next week is an easy way to show you remembered.
Which smell do you secretly like that most people complain about?
Why ask it
Most people have one and assume it is only them: a fresh permanent marker, the chlorine at an indoor pool, a heater switched on for the first time since spring. Agree with hers if you honestly can, and confess yours either way.
What is the oddest thing you refuse to throw away?
Why ask it
What would have to happen for it to go? That is the follow-up for a drawer of ticket stubs, a dead phone or a single earring whose partner left years ago. It sits close to sentimental, so if the object belonged to someone she misses, drop the jokes and just listen.
What is the least scary thing that has ever made you jump out of your skin?
Why ask it
It asks about fear without asking for a real one, which keeps it light. Her own reflection, a toaster and a leaf that moved are all respectable answers. Act out your own worst jump before she tells hers.
Which seat is yours on the couch, in the car or at the table, and what happens if someone takes it?
Why ask it
Almost everyone has a seat and a quiet policy for defending it. Does she say something, or stand nearby until the person moves? Useful to know before you ever sit down at her place.
Can you wiggle your ears, raise one eyebrow or roll your tongue, and which one took practice?
Why ask it
Best in person or on a video call, because she will try all three while she answers. Show whichever you can do and fail loudly at the others. Keep it to face and hand party tricks like these, since this is not an opening for anything more personal.
What strange thing do you do to fall asleep?
Why ask it
It suits a late text, when she may be about to do it: plan an imaginary house, put on a recording of a man describing train routes, leave one foot outside the blanket. You are after the ritual, so do not let it become a conversation about sleeping badly.
What tiny thing annoys you that nobody else seems to notice?
Why ask it
Pet peeves get weird when they get exact: a clock that ticks unevenly, a cupboard door left open one inch. Agree that it is a crime, then make a note never to commit it.
Do you still follow a walking rule you made up as a kid, like never stepping on the cracks?
Why ask it
If she says yes, walk somewhere together and have her show you: only the dark tiles, the same foot onto every curb, a tap on each third fence post. If she says no, tell her yours and watch her remember one.
What do you wish on, eyelashes, 11:11 or birthday candles, and do you ever tell anyone the wish?
Why ask it
The wish itself is the one thing to leave alone. Ask about her success rate instead. Someone who still wishes at 11:11 may start texting you at 11:11, which is a nice thing to have set off.
Brain and dreams
What is the strangest dream you have ever woken up from, and did you try to get back into it?
Why ask it
The second half tells you whether it was good strange or bad strange. Listen without interpreting it, since nobody wants their dream explained back to them. If she did get back in, find out whether it carried on from where it stopped.
Do you dream in color, and are you always yourself in your dreams?
Why ask it
Plenty of people have never checked, and the pause while she thinks is part of the fun. Some watch their dreams like a film and some play a different character entirely. Ask about the last one she remembers and whether it had a soundtrack.
Which ordinary word have you stared at until it stopped looking like a real word?
Why ask it
It tends to be the plainest ones, 'door' or 'which' or her own name halfway down a form. Try it together on a napkin with a word she picks, and see which of you loses the spelling first. It takes thirty seconds and suits a pause in the conversation.
Do you ever get the feeling you have lived this exact moment before, and what do you think is going on?
Why ask it
Her theory matters more than whether it happens: a glitch, a dream she forgot, a memory filed twice. There is no need to settle it. If she turns the question on you, have a theory ready that is stranger than hers.
What do you think about when you are staring at nothing?
Why ask it
Ask it gently when you catch her drifting, and never as a complaint that she was not listening. A good answer is an imaginary argument or a full redesign of her kitchen. 'Nothing at all' is a real answer too, and worth asking how she manages it.
When you read a text, whose voice is it in: yours, the sender's or nobody's?
Why ask it
She may not know until she checks, so send her a message to test it on. Then ask what your voice sounds like in her head and whether it is accurate. That last part is why it belongs with someone you already text.
What sound do you find more satisfying than it should be?
Why ask it
A can opening, a stapler, snow under a boot. She may do an impression, which you should encourage. It pairs well with asking which sound she would remove from the world.
What did you believe as a kid right up until someone broke the news?
Why ask it
Good ones sound like this: the car's turn signal knew the way, you could dig a hole to another country, the ice cream truck only played music when it had sold out. The person who corrected her was often an older sibling, and rude about it. Trade one of your own.
Which toy did you believe had feelings, and did you ever apologize to it?
Why ask it
Kids who believed it usually ran a system: taking turns on who got the pillow so nobody felt left out, saying sorry after dropping one down the stairs. Get the toy's name and where it lives now. If the answer is 'still on my bed', that is not something to tease her about.
What game did you invent as a kid, and what were the rules?
Why ask it
Games made up by kids have rules that only make sense from inside, like a couch that is a ship with one safe cushion. Let her explain all of it. Asking to play a round is the right level of ridiculous if you are somewhere with furniture.
What did you plan to be when you grew up that is not actually a job?
Why ask it
A mermaid, a cat, a princess who is also a vet. Ask what the plan involved and when it was dropped. It is a gentle way to hear what she was like at six.
What were you strangely obsessed with as a kid: horses, volcanoes, ancient Egypt?
Why ask it
Most people had a phase and can still recite facts from it at speed, so ask for three right now. If the obsession never fully ended, that is the best possible outcome and you should ask to see the proof.
What is the closest you have come to believing in ghosts?
Why ask it
This gets you a story instead of a yes or no: a door, a cold spot, a grandmother's house. Hear it out as if you believe it, at least until she finishes. Leave it out if she has lost someone recently, because it can turn serious quickly.
What harmless conspiracy theory would you start if you wanted it to catch on?
Why ask it
Inventing one is funnier than confessing to one: that a certain month was added later, that all pigeons report to the same office. Help her build the evidence. Keep it to nonsense and change the subject if it heads toward real politics.
The two of us
What was the oddest thing you thought about me before we had really talked?
Why ask it
Only ask once the two of you are comfortable, because you have to be able to hear the answer. 'I thought you were much taller' and 'I assumed you hated me' are both normal. Tell her your wrong first guess about her, and keep it kind.
If the two of us were animals, which two would we be, and would they get along?
Why ask it
She chooses both animals, which tells you how she sees you. An otter and a heron is a good sign, while a cat and a vacuum cleaner needs discussing. Do not sulk about your animal.
If we had to pull off a harmless heist together, what are we stealing and who is the lookout?
Why ask it
The target should be ridiculous: one garden gnome, the last slice at a party, a single shopping cart. Dividing the roles is light teasing about who stays calm and who would wave at the security camera. Save it for someone who already jokes with you.
What is the weirdest thing we have in common so far?
Why ask it
It asks her to look back over what she knows about you, so it only works after a few real conversations. Hating the same vegetable counts. If she cannot think of one, suggest finding one now by trading strange opinions until two match.
On a scale of one to ten, how weird am I, and what moved the number?
Why ask it
You are asking to be teased, so take the number without arguing. Anything from five to eight is affectionate. Ask what would raise the score by one, and consider doing it.
What would the two of us be hopeless at doing together?
Why ask it
Naming a shared failure is a quiet way of imagining doing things together at all, whether it is assembling furniture, rowing a boat or agreeing on a movie in under an hour. If one of them sounds fun, suggest trying it to prove her wrong.
If we got lost in the woods, which of us panics first and which one starts talking to the trees?
Why ask it
Let her assign both roles before you object. She will probably keep the sensible one for herself, and you should accept the trees. Her first move is the follow-up, and it tends to be more practical than yours.
What strange job can you picture me doing a little too well?
Why ask it
Lighthouse keeper, game show host, the voice that announces the stops on a train. Whatever she picks is a compliment in disguise, so ask what gave her the idea. Offer one for her that is odd but flattering.
If we started a two-person club, what is it for and what is the one rule?
Why ask it
The club can be for anything small: people who hate wet sleeves, ranking every bench in the park. Her one rule tells you what she thinks you need reminding of. If the club sounds fun, hold the first meeting.
If you had to save me in your phone under a name that is not my name, what would it be?
Why ask it
Contact names tend to come from one moment: 'Umbrella Incident', 'Do Not Lend Books'. Whichever she picks tells you which moment stuck. Propose one for her, let her veto it, and change the contact where she can see you do it.
What would our secret handshake involve?
Why ask it
Best asked in person, because the obvious next step is building it. Start simple and let her add the ridiculous parts. Over text, or if a handshake feels like too much, a code word does the same job.
What is the strangest place we could go on a date that you would still say yes to?
Why ask it
Only ask if dates are already on the table between you. A hardware store, a dog show and the arrivals hall at the airport, to watch the reunions, are all fair answers. If she names somewhere real, you have just been handed a plan.
What is the weirdest question anyone has ever asked you, and did you answer it?
Why ask it
It makes a good last question, because the answer is often yours from ten minutes ago, and you should accept the title. If it was something a stranger asked that made her uncomfortable, do not repeat it for a laugh. Otherwise ask it again and see whether she answers this time.
How to be weird without being creepy
Practical guidance for the conversation itself
Making a strange question land as playful
Ask it straight
A strange question is funniest when it is asked as if it were ordinary. No 'this is going to sound weird, but', and no laughing before you reach the end. Say it, then wait, and let her be the one who decides it is ridiculous.
Know your own answer first
Before you ask about her lucky socks or her vegetable, know yours. When she stalls, answer first, and pick something more embarrassing than you expect hers to be. A weird question with no answer from you feels like a test.
One, then back to normal
A single odd question in the middle of a normal conversation stands out. Five in a row sounds like you are reading from a page. Ask one, go where her answer goes, and come back for another only when the talk slows down.
Stay with her answer
When she says she would be a potato, the next question is about the potato. Most notes suggest a follow-up. Use it, then ask one more thing of your own before you think about moving on.
Keep what she tells you
The name of her planet, the thing she counts on the stairs, the animal she invented: these are yours to bring up again. Mentioning one a few days later shows you listened, and it turns a passing joke into something only the two of you have.
Where each group fits
The first conversation
Stay in Openers and the lighter half of What if. Nothing in them is personal, and one sentence is enough of a reply. Food and animals is just as safe, and easy to bring up anywhere there is a menu or a dog in view.
Over text
Short ones travel best: the lemonade tears, the worst pillow, the emoji she does not trust, the bird that is afraid of heights. Send one with no explanation and give it time. A reply that comes back with a question of her own means it worked.
On a date or a long walk
Habits and quirks, and Brain and dreams, need more room, because the good answers are stories. Trade them evenly. If she tells you about the toy she used to apologize to, she is owed your strangest dream.
Once she knows your humor
The two of us comes last for a reason. Asking how weird you are, or what the pair of you would steal, assumes she already enjoys joking with you. If you are not sure she does, stay in the earlier groups a while longer.
Strange, never creepy
Weird about the world, not about her looks
Nearly everything on this page is about pigeons, soup, superstitions and dreams. Nothing asks about how she looks or what she wears, and your follow-ups should stay in the same place. The moment a weird question becomes a way to comment on her body, or to push for something more personal than she offered, it is creepy, and no delivery fixes that.
Never turn 'weird' against her
If she admits to counting stairs or naming her car, the reply is 'me too' or 'that is excellent', never 'wow, that is strange'. You asked for the odd thing. Treating it as a flaw teaches her not to tell you the next one.
Private stays private
Search histories, sleep stories and what she does when nobody is around are hers to edit. Take the version she offers, never ask to see the phone, and do not pass her answers on to your friends as material.
Notice when it stops being a joke
A few of these can touch something real: the thing she will not throw away, the ghost story, a dream that was not a funny one. If her tone changes, stop joking and listen, or move to something lighter.
When one falls flat
She does not get it
Do not explain the joke. Say 'fair, that one was a lot' and ask something normal. A missed question costs nothing if you let it go quickly, and plenty if you repeat it louder.
She says she does not know
Offer two silly options and let her pick, or give your own answer and ask her to rate it. Some people need a moment before nonsense feels allowed. If the second try gets nothing either, she may simply not be in the mood today.
You are doing all the asking
Three questions with no question back is a signal. Switch to ordinary conversation about her day and let her set the pace. Weird questions are seasoning, and nobody wants a plate of salt.
She is weirder than you
Now and then she will answer the pigeon question with a ten-minute plan and three questions of her own. Keep up as best you can and enjoy it. You were hoping to find someone who talks like this.