Funny Questions to Ask a Girl
For anyone getting to know a girl and hoping to make her laugh before trying anything cleverer. The 98 funny questions here are in six groups: silly and random ones, absurd what-ifs, would you rathers, harmless debates, embarrassing stories that are safe to tell and questions made for texting. Every one is clean, and each has a short note with the follow-up that keeps the joke going.
Want questions from the whole vault instead? Try the random question generator.
The questions
Each question, and why to ask it
Silly
What would your warning label say?
Why ask it
She gets to roast herself in one line: 'Do not speak to before coffee', 'May burst into song without notice'. Give yours, then ask what her best friend would add in the small print.
Which animal do you think is quietly judging all of us?
Why ask it
Cats are the easy answer, so have her make the case for a less obvious suspect, like geese or one particular neighborhood crow. What keeps it going is the verdict: what has that animal concluded about her specifically?
If you opened a restaurant that served only one dish, what is the dish and what is the place called?
Why ask it
The name is where the comedy is, so do not let her skip it. Once she has both, ask what the angriest one-star review of the place would say.
What is the worst name you could give a dog and still have to shout across a park?
Why ask it
Picture the shouting and it gets funnier: 'Gary, drop it', 'Come here, Tax Return'. Trade names until one of you gives up, and if she has a dog, ask how it really got its name.
What are you fiercely competitive about that is not actually a competition?
Why ask it
Most people have one: being first off the plane, guessing the twist before anyone else, walking faster than the stranger alongside. The follow-up is who she is racing, and whether that person has any idea there is a race.
What job would your pet have if pets had to earn their keep?
Why ask it
If she has no pet, lend her a friend's or one she grew up with. Cats tend to land in middle management and dogs at the door of a hardware store, greeting everyone, so the follow-up is whether hers would ever be promoted.
How long would you last on a baking show, and what would send you home?
Why ask it
She will probably know exactly which round ends her: bread, anything with layers or the judges' faces. 'What would you bake to stay in?' gets you her one reliable recipe, which is worth knowing.
Which movie or TV character would you least want beside you on a ten-hour flight?
Why ask it
The fun is in her reasons: a character who sings, one who narrates, one who is always in the middle of a crisis. Flip it afterward and ask who she would choose for the seat instead.
What would you put on a billboard purely to confuse people?
Why ask it
The best answers are short: 'He knows', or a large photo of a potato with no caption. Location is half the joke, so find out where it goes, then propose a second billboard a mile further on that makes things worse.
What is the least useful prize you have ever won?
Why ask it
Raffles, school fairs and attendance trophies produce most of these. Where is the prize now? That is the real story, particularly if it was a goldfish or a ham.
What are you terrible at but refuse to stop doing?
Why ask it
Whistling, bowling, singing the high part in the car. It is a brag and a confession at once, and the natural next step is offering to be terrible at it together sometime.
What is the worst thing a waiter could say while setting down your plate?
Why ask it
'Chef says good luck' is hard to beat, but let her try. It works best when you are sitting at a table waiting for food, and you can keep adding lines until the real plates arrive.
What is the oldest thing in your bag or car that has no business still being there?
Why ask it
She can check on the spot, which turns it into a small show and tell: a loyalty card for a place that closed, a single glove, sauce packets from another era. Have your own oldest receipt ready.
What snack would you happily be the unpaid spokesperson for, and what is the slogan?
Why ask it
The slogan is what turns a favorite food into a bit, so hold out for it. You also now know what to turn up with if you ever need to apologize for something.
What were you scared of as a kid that makes you laugh now?
Why ask it
Keep it to the silly ones, like the bathtub drain or one particular puppet on television, and match hers with one of yours. If she names a fear she still has, believe her and do not test it.
How do you leave a party: the long goodbye, a wave from the door or vanishing without a word?
Why ask it
She will know which one she is at once, and she will have opinions about the other two. Long-goodbye people usually hold a record, so go after the number: how many minutes between 'I should go' and the door?
If you started a band tomorrow, what is it called and what can you actually play?
Why ask it
'Actually' is the catch, since most imaginary bands turn out to be four people on tambourine. Offer to join, name your equally useless instrument and ask what the first album is called.
What is your most-used excuse, and who has stopped believing it?
Why ask it
'My phone died' and 'I was just about to leave' cover a lot of ground. The second half brings in a friend or a parent who knows her too well, and that person is your next question.
What food from a cartoon or movie have you always wanted to try?
Why ask it
Drawn food always looks better than the real thing: the towering sandwich, the glowing soup, the pie cooling on a windowsill. If she ever tried to make it at home, you want to hear how that went.
What song do you know every word of and wish you did not?
Why ask it
Expect a theme tune or a hit from the year she was eleven. The follow-up is obvious and slightly mean, which is to request the first line. Sing the next one if you know it.
What if
If your personality were a pasta shape, which shape is it?
Why ask it
It sounds like nonsense and gets surprisingly reasoned answers: bow ties for trying too hard, lasagna for hidden layers. Then have her assign you a shape. Accept the verdict, even if it is plain macaroni.
If you could pull one harmless prank on your whole town, what would it be?
Why ask it
'Harmless' steers her toward the inventive ones: tiny hats on every statue, every public clock set four minutes off. Then play detective together and work out which of her friends would name her as the suspect within the hour.
If you were handed a dragon the size of a house cat, what would you name it and where would it sleep?
Why ask it
Making it small turns an adventure into a household problem. Keep asking about logistics: what it eats, what it has already set on fire, whether the landlord knows.
If you could only eat foods of one color for a year, which color keeps you happy?
Why ask it
Beige is a stronger pick than it sounds, since bread, fries and pasta all live there. Push back with what she would have to give up, then choose a rival color and compare menus.
If you were allowed to rename one everyday object, what gets a new name?
Why ask it
A fork becomes a food rake, gloves become hand socks. Start using her new word for the rest of the conversation, because a running joke she invented is the best kind.
If your friend group were a sitcom cast, which one are you: the sensible one, the chaos or the one with the catchphrase?
Why ask it
She will name her role and then describe everyone else to prove it, so you meet the whole friend group in one answer. 'Which episode do they still bring up?' gets you the story.
If you could talk to just one species of animal, which one has the best gossip?
Why ask it
Pigeons see everything, house cats hear everything, and seagulls have no shame. The second question is what she would ask first, which tends to be more revealing than the species.
If you were stuck inside one movie for a week, which would you choose and how soon would you wreck the plot?
Why ask it
Choosing is the sensible half and wrecking is the fun one: telling the hero the twist, eating the props, going home early. Which character would be most annoyed with her is a good place to take it next.
If a narrator followed you around all day, whose voice would it be and what would they say about this morning?
Why ask it
A nature documentary voice suits nearly any morning. Do an impression of the narration if you can manage one, or ask her to write the line for the moment she finally got out of bed.
If you had a time machine that could only be used for petty reasons, where is your first stop?
Why ask it
Small stakes make this easy to answer honestly: winning an old argument, reaching the last pastry before a stranger did, unsending one message. Offer your own petty trip in return and argue about whose is more justified.
If you got one superpower that was no help at all in an emergency, what would you want it to be?
Why ask it
This is the classic superpower question with the heroics taken out. Once she has picked, say never losing a hair tie or always choosing the fastest checkout line, invent the one emergency where it would save the day and pitch her the movie.
If you won a lifetime supply of something but had to store all of it in your bedroom, what would you pick?
Why ask it
The storage rule is what makes her think: a lifetime of ice cream is a flood, a lifetime of socks is a mattress. Ask how she would be sleeping in there by year three.
If an alien asked you to explain one ordinary human habit, which would defeat you?
Why ask it
Clapping, blowing out candles on food, saying 'no, you hang up'. Play the alien and keep asking 'but why' until the explanation falls apart, which it will.
If you had a robot that did exactly one chore perfectly and nothing else, which chore is it and what is the robot's name?
Why ask it
Whichever chore she picks is the one she hates most, and now you know it. Do not let her skip the name, since she will be living with the thing.
If you were made queen of a very small country, what would the national dish and the national sport be?
Why ask it
Two decisions and she has built a whole place, usually one where the sport is napping or competitive snacking. Apply for citizenship and ask what the entry requirements are.
If the two of us had to run a bake sale table for an afternoon, who charms the customers and who eats the stock?
Why ask it
One for a girl you already get along with, since it casts the two of you as a team without making anything of it. Take the worse job for yourself, then negotiate what the table sells and what the sign says.
Would you rather
Would you rather have one shoe that always squeaks or a sneeze that sounds like a duck?
Why ask it
Both are ridiculous and neither costs anything to answer, which makes it a good first one. Then test her choice in the worst places: the shoe in a library, the sneeze in the middle of a job interview.
Would you rather have to whisper everything for a week or shout everything?
Why ask it
Each choice ruins a different part of the week, so walk her through a day with it: ordering coffee, sitting in a movie theater, telling someone a secret.
Would you rather have a theme tune that plays whenever you enter a room or a laugh track that follows your jokes?
Why ask it
The theme tune flatters, and the laugh track is a gamble because it might stay silent. If she takes the tune, she has to hum it. If she takes the laughs, try one of her jokes on the imaginary audience.
Would you rather have to wear a cape everywhere or a small bell that rings whenever you move?
Why ask it
Capes are the showy choice, and the bell rules out ever sneaking a snack again. Cape people owe you the color. Bell people owe you the name of whoever at home would be glad of the warning.
Would you rather give up cheese for good or give up every kind of dessert?
Why ask it
You find out quickly whether she is a savory person or a sweet one, which is handy when you are choosing where to eat. Raise the stakes afterward: would she take cheese back if it cost her fries?
Would you rather sing everything you say for a day or dance everywhere you walk?
Why ask it
Her pick shows which she minds less, being heard or being watched. Ask for the style either way, since opera and country make for very different days.
Would you rather be the funniest person in the room or have the laugh that sets everyone else off?
Why ask it
It splits the performers from the audience, and plenty of people are proud to be the audience. Tell her which one she seems like so far, as long as you mean it kindly.
Would you rather have a pet that talks but only complains or a pet that sings but only at five in the morning?
Why ask it
Ask what the complaints would be about, since she will end up doing the pet's voice, and that is where it gets funny. Anyone who picks the singer is a morning person or bluffing.
Would you rather live in a house where every floor is a trampoline or one where every staircase is a slide?
Why ask it
The practical problems are the game: carrying soup across a trampoline, getting back up a slide. Take the other house and argue for it through a whole imaginary day.
Would you rather always be ten minutes late or always be an hour early?
Why ask it
There is a true answer inside the joke, because she almost certainly leans one way already. Somebody in her life will be the opposite kind, and how the two of them ever arrive anywhere together is the story.
Would you rather everyone could see your most-played songs or your daily screen time?
Why ask it
Both are a little too honest, which is why it works. Whichever she protects, offer to trade the real song or the real number, and go first.
Would you rather have to high-five everyone you walk past or bow to every dog you meet?
Why ask it
The high-fives wear her out within a block, and the bowing is only a problem near a dog park. Whichever she takes, act out the worst case: a crowded hallway between classes, or one dog walker holding six leashes.
Would you rather get hiccups every time you fib or giggle every time you are nervous?
Why ask it
Either way she becomes easy to read, and she knows it, so expect some bargaining over the terms. A good follow-up is which of the two her friends would say she nearly has already.
Would you rather hold the world record for the loudest yawn or finish last in a race the whole town came out to watch?
Why ask it
One is fame for something silly and the other is losing at something hard. Take whichever she leaves and defend it, then trade ideas for the ridiculous record each of you would honestly have a shot at.
Would you rather have endless fries that are always slightly cold or one perfect fry a day?
Why ask it
Quantity against quality, settled with potatoes. Ask what she would do with the one perfect fry: eat it at once, save it for the evening or build a small ceremony around it.
Would you rather have a ten-second rewind button for your own life or a mute button for everyone else?
Why ask it
Rewind fixes what she just said, and mute fixes what everyone else is saying. Find out which moment from this week she would have rewound, and do not be hurt if you are the first person she mutes.
Debates
Does pineapple belong on pizza, and how far would you go to defend your answer?
Why ask it
Everyone has heard this one and has a side ready, which is why it still works as an opener. Whatever she says, take the other side with a straight face for one round, then find out what her real order is.
Is breakfast for dinner a treat or a sign the day went wrong?
Why ask it
Pancakes at eight in the evening mean very different things to different people. Find out what she would order. You now have a low-pressure plan to suggest later.
Should the toilet paper hang over the top or down the back?
Why ask it
No stakes and plenty of passion, as household debates go. The better question is hiding behind it: has she ever quietly turned a roll around in someone else's bathroom?
What is the correct way to eat a sandwich cookie: twist it open, dunk it or bite straight through?
Why ask it
She will have a method and a low opinion of the others. It goes better with cookies on the table, so if you can, buy a pack and hold a demonstration.
Is a sandwich better cut corner to corner or straight across?
Why ask it
Triangle people will tell you it tastes better and cannot explain why. Make her try. Then find out who cut her sandwiches when she was little and which way they went.
Which sequel is better than the original, and are you ready to be told you are wrong?
Why ask it
Announcing the disagreement in advance makes it a game instead of a quiz about her taste. If you have not seen her pick, say so and ask her to sell it to you in one sentence.
Subtitles: always on, or only when you have to?
Why ask it
You are getting a preview of how a movie night with her would go. Subtitle people often have a line they misheard for years before the words appeared on screen, and that is worth hearing.
How old does a show have to be before spoilers are fair game?
Why ask it
Get her to commit to a number of years, then threaten to test the rule on something she has not finished. Stop before you give anything away for real, because that joke does not survive being carried out.
When is it acceptable to start playing holiday music?
Why ask it
There are November people and December people, each sure the other is the problem, so find out which she is and which song she would ban outright.
Are voice messages a gift or a homework assignment?
Why ask it
Worth asking before you send her a four-minute one. If she likes them, ask about the longest she has ever received and what on earth it was about.
Cat person or dog person, and what would it take to get you to switch sides?
Why ask it
The first half is small talk and the second half is the question. There is usually one particular animal that nearly converted her, so ask about that one.
Does sleeping with socks on make someone a genius or a menace?
Why ask it
Nobody shrugs at this one. Let her rant, defend the opposite position for fun, and then ask what other small habit she would put in the same category, like chewing ice or leaving cabinet doors open.
Who owns the armrests in the middle seat of a plane?
Why ask it
Plenty of people hold that the middle seat gets both as compensation, and it is fun to see whether she agrees. Window shade rights come next: who decides when it goes down?
Do you say 'gif' like 'gift' or like 'giraffe'?
Why ask it
Pointless and good for ten minutes anyway, especially if you say it the other way for the rest of the conversation and see how long she can stand it.
How long can food sit on the floor before it is no longer yours?
Why ask it
Every five-second rule has fine print, and hers will depend on what fell and where. Ask for the one item she would rescue no matter how long it had been down there.
Embarrassing stories
What is the most dramatic way you have ever reacted to a bug?
Why ask it
Leaving the room counts, and so does leaving the building. Ask who dealt with the bug in the end, and promise not to bring the story up the next time a moth appears.
When did you last get the giggles at the worst possible moment?
Why ask it
The setting is always somewhere silent: an exam hall, an assembly, a serious meeting. What set it off is the part to go after, because it is nearly always something tiny, along with whether anyone else caught it from her.
Have you ever called a teacher 'Mom' by accident, or something just as bad?
Why ask it
It is common enough to be an easy first confession, and it gives away nothing she would mind a stranger knowing. How long the class kept it going is the story. Own up to yours afterward.
How do you recover after waving back at someone who was waving at the person behind you?
Why ask it
Her recovery move is the answer: the wave that becomes a stretch, the sudden deep interest in her phone. Act out your own, since this one is funnier shown than told.
What is your most spectacular fall, and who saw it?
Why ask it
Stairs, ice and a perfectly flat sidewalk are the usual culprits. Check that nothing was really hurt before you laugh, then ask what the witnesses did, which is often the part she remembers best.
What performance did you make your family sit through as a kid?
Why ask it
Living-room shows come in a few kinds: the dance routine with a costume change, the magic act with one trick, the play with tickets sold at the door. If a recording exists, she decides whether you ever see it, even if her 'no' comes suspiciously fast.
What did you get wrong about how the world works when you were little, like thinking teachers lived at the school?
Why ask it
The example shows her the kind of thing you mean, and nearly everyone has one they held on to for far too long. Do not correct the logic. Find out who finally broke the news and how she took it.
What reply have you blurted out that made no sense, like saying 'you too' when a waiter said to enjoy your meal?
Why ask it
The example in the question tells her the bar is low. Once she has given hers, swap a few more: 'love you' to a delivery driver is a strong entry.
What is the funniest thing you ever got in trouble for at school?
Why ask it
Keep it to the comic offenses, the intercepted note or the laugh she could not hold in. Ask whether the punishment fit the crime and whether her parents ever found out. If she is still at school, ask about this year.
Which door, gate or machine has beaten you in front of the most people?
Why ask it
A push door pulled four times, a ticket barrier, a self-checkout that called for help in a loud voice. Sympathy is the right response, followed by your own defeat at the hands of something with clear instructions.
What is the silliest thing you have done on autopilot, like putting the milk away in the cupboard?
Why ask it
These are small and harmless, so she can tell three in a row without feeling exposed. Ask what the strangest place is that she has ever found her own keys.
What have you said or done on a call before realizing you were not on mute?
Why ask it
It works for a video class as well as a work meeting. Most of these are harmless, like singing or arguing with the dog, but tread lightly if hers had real consequences. The hero of the story is whoever told her.
What went wrong on your first day at a job, a school or a team?
Why ask it
First days come with wrong rooms, wrong names and uniforms that do not fit, and the stories improve with age. A kind follow-up is how long it took before she felt she knew what she was doing.
What is the oldest post or caption of yours that you hope stays buried?
Why ask it
She can describe it without showing it, and that should be enough for you. Do not go looking afterward. Describe your own worst one so the trade is fair.
Have you ever sat down in the wrong class, meeting or movie, and how long did you stay?
Why ask it
How long she stayed measures how much she hates causing a scene. Some people walk straight out and some watch forty minutes of a film they did not choose, so ask whether it was any good.
What have you said in your sleep, according to witnesses?
Why ask it
Sleep talk is funny because she cannot be held responsible for it: orders shouted at nobody, a full sentence about ducks. If she has no idea, the follow-up is which friend or sibling would.
Over text
Where is your day on a scale from 'lost a sock' to 'found money in an old coat'?
Why ask it
It checks in on her without reading like a check-in, and she can answer in four words. Find out what would move the score up a notch, then see whether a message from you can do it.
What is the weirdest thing within arm's reach of you right now?
Why ask it
It has to be answered from wherever she is sitting, which makes the conversation feel live. If she sends a photo of it, send one back of yours, but leave the photo up to her.
Tell me about your day in three emojis and I'll guess what happened.
Why ask it
The guessing is where you get to be funny, so guess confidently and wrongly at first. She will correct you, and the correction is the real story of her day.
What would your two-star review of today say?
Why ask it
Two stars, not one, so the day is allowed a redeeming feature. Reply in the voice of the management, apologizing for the inconvenience and promising a better tomorrow.
Invent the worst ice cream flavor you can, and I'll tell you honestly whether I'd still eat it.
Why ask it
Each turn is one line, so it suits texting. Send a flavor back for her to judge, and keep a running score if it lasts more than three rounds.
What is the funniest name you have someone saved under in your phone?
Why ask it
There is a story behind every odd contact name, and it usually introduces a friend or a relative. Asking what she has you saved as is fair, but only once the conversation is already playful.
What is your most active group chat called, and who came up with the name?
Why ask it
Group chat names are inside jokes that got preserved, so the explanation takes a few messages. That is the point. Ask what the chat is arguing about today.
What has autocorrect done to you that you have still not forgiven?
Why ask it
It might be a word her phone refuses to learn, or one message that reached a boss with the wrong noun in it. Share the correction your own phone keeps making, preferably by letting it happen.
Send me two truths and a lie about your week, and I'll guess which is which.
Why ask it
The old party game is easier by text, since she has time to make the lie convincing. Guess, explain your reasoning like a detective, and then take your own turn.
What song is stuck in your head right now, and whose fault is that?
Why ask it
Blame is the fun half: a sibling, a store, a video she watched once. Listen to the song before you reply, so that you can complain about having it too.
Give me a completely made-up fact, stated with total confidence.
Why ask it
It asks her to write a joke, so save it for someone who has already shown she likes to play. Reply as if you believe it and ask a serious question about her 'research'.
On a scale of one to ten, how bad a pun can you put up with right now?
Why ask it
Have the pun ready before you send this, because the scale is only a drumroll. Send it whatever number comes back, and if she answers with a worse one, you have found someone to trade them with.
If your name had to change to the last thing you ate, who am I talking to?
Why ask it
Use the new name for the rest of the conversation, because 'Good night, Toast' is funnier than it has any right to be. Tell her yours without being asked.
Finish this sentence: 'I should never be trusted with...'
Why ask it
Fill-in-the-blank works well typed because she can take a minute over it. Answers run from scissors to the group's dinner reservation, and 'what happened' gets you the story.
One of these has to vanish forever: tacos, pizza or pasta. Which one do you sacrifice?
Why ask it
Quick to answer and easy to be outraged by, which is what you want from a message sent in the middle of a dull afternoon. Defend the one she gives up, then let her set you a harder three.
How to get the laugh and keep it going
Practical guidance for the conversation itself
Asking so it lands
Go first, and answer badly
A silly question is easier to answer once someone else has looked silly. Give your own answer before she has to, make it worse than hers is likely to be, and keep it to a sentence so the turn comes straight back to her.
Stay on the one that worked
When a question gets a laugh, do not reach for the next one. Use the follow-up in its note, then ask one more thing about her answer. Ten minutes on a cat-sized dragon is a better conversation than ten questions that each got one line.
Laugh with her, not at her
Nothing on this list jokes about how she looks or compares her with other girls, and your follow-ups should not either. Tease the logic of her answer, never the person giving it. In Embarrassing stories, your job is to enjoy the story and then tell one of your own that is at least as bad.
Lose the debates gracefully
In Debates and Would you rather, take the other side for a round because agreement ends the game. Then concede with some style. Nobody has ever been charmed by a person who needed to win an argument about sandwich geometry.
Bring one back later
The funniest thing you can say on the second day is something from the first: her renamed fork, her doomed baking show round, the name of her band. A callback shows you were listening, which matters more than any of the questions.
Which group suits which moment
You have only just met
Start in Silly or Would you rather. They need no history and nothing personal, and she can answer in five seconds or run with it. Ask one, not three, and let ordinary conversation carry on from wherever her answer goes.
On a date
Debates suit a table with food on it, and several can be settled on the spot. Leave Embarrassing stories until you are both already laughing, and trade evenly: every story she tells should cost you one of yours.
Over text
The Over text group is written to be answered in a line, and most of What if and Would you rather travel well too. Send one question, not a list, and give it time. If the reply is a single word, the kind move is to let the thread rest until tomorrow.
When you like her
You do not need a special set of jokes for someone you like. What changes is what you do with the answers: remember the snack she would advertise and the song she cannot stand, and use them weeks later. The bake sale question in What if is the one here that puts the two of you on a team, so save it for when she is already joking back. If she starts sending questions of her own, that is a good sign, and it is the point to suggest doing one of these in person.
When a joke does not land
A question gets a blank look
Say 'that sounded better in my head' and move on. Owning a flop is funnier than the question would have been, and explaining why it was meant to be funny never rescues it.
A story turns out not to be funny to her
What reads as a harmless embarrassment on a list can still sting for the person it happened to. If her face changes or the reply goes short, do not push for the rest. Tell one of yours or change the subject, and never repeat her story to anyone else.
You are doing all the joking
If you have asked five in a row and she has asked nothing back, stop performing. Ask something plain about her day and listen to the answer. Funny questions are a way into a conversation and cannot stand in for one.
She is funnier than you
This is the good outcome. Laugh properly, say that was better than yours and let her have the room. Being a generous audience is easier than being a comedian, and it tends to be remembered more fondly.