Questions to Ask a Girl
For anyone getting to know a girl they like and hoping to do better than 'so, what do you do'. There are 175 questions to ask a girl here, in six groups: easy openers, interesting and personal questions to get to know her, funny questions, flirty questions that stay playful, deep questions and ones that work over text, easiest first within each group.
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The questions
Each question, and why to ask it
Openers
What's the story behind your name?
Why ask it
Almost everyone has one: a grandmother, a compromise, a character in a book her mother loved. It is personal without being private, and it helps you remember her name, which is only polite.
What's your comfort rewatch, the thing you put on when you can't decide?
Why ask it
Asking for the rewatch instead of the favorite gets a more honest answer. Nobody's comfort show is the impressive one, and what she finds soothing tells you a fair bit about her.
What's the short version of how you ended up living here?
Why ask it
'The short version' keeps it light and lets her decide how much history to include. If the long version sounds interesting, ask for it another day. She will notice that you remembered.
Did you grow up with pets, and which one had the biggest personality?
Why ask it
Pet stories come pre-loaded with affection and comedy, so even a guarded person relaxes. If she never had one, ask what she begged for and was refused.
What will you always stop to look at, no matter how late you're running?
Why ask it
It shows what pulls her attention when she is not managing it: dogs, bookshop windows, a good sunset, houses with the lights on. You also get something to point out the next time you are out together.
Whose cooking do you miss the most?
Why ask it
A grandmother's dumplings, a dad's one good curry, the roommate who baked when stressed. She ends up telling you about a person and a time in her life, which is more than the question seemed to ask. If the cook is no longer around, let her decide how much to say.
What's the last thing you learned that you immediately had to tell someone?
Why ask it
Curiosity is attractive, and the fact she could not keep to herself shows what her mind does when nobody is grading it. It might be how deep a shipwreck sits or why a cheese has holes. Ask who she told.
What song do you put on when a day needs rescuing?
Why ask it
More useful than 'what music do you like', which makes people freeze and try to sound cool. A rescue song is chosen for how it works, not how it looks, so the answer is unguarded.
Are you the oldest, the youngest, somewhere in the middle or an only child, and does it show?
Why ask it
'Does it show' is the half that gets her talking, because everyone has a theory about what their place in the family did to them. Be ready to say which one you are and whether you fit the type.
What hobby did you take up with huge enthusiasm and then quietly drop?
Why ask it
There is usually a ukulele, a sourdough starter or a set of watercolors in a closet somewhere. Admitting to an abandoned project is an easy bit of honesty that invites you to share yours.
What was on your bedroom wall when you were twelve?
Why ask it
An easy laugh at her younger self, whether it was band posters, a collage of friends or glow-in-the-dark stars. You hear what she loved before anyone told her what was cool, so be ready to admit what was on yours.
What trip would you take again exactly as it was, and what made it that good?
Why ask it
The destination matters less than the second half. If it was the people, the freedom or the food, you now know what she is after when she gets away from routine.
What do you always have with you, even if you're only leaving the house for ten minutes?
Why ask it
The answer is a small, exact picture of how she gets through a day: lip balm, headphones, a paperback, an emergency snack. It is also excellent gift information for later.
What food could you not stand as a kid and now love?
Why ask it
A tiny story about changing, told through mushrooms or olives. It is impossible to get wrong, which makes it a good one for the first few minutes when both of you are still nervous.
Who's the funniest person you know, and what makes them so funny?
Why ask it
She gets to talk about someone she loves, and you get a working definition of her sense of humor. Do not try to compete with the person she names. Just enjoy the secondhand material.
What's the oddest job you've ever had, and what did it teach you?
Why ask it
Better than 'what do you do', which everyone is tired of answering. Odd jobs come with characters and disasters, and the lesson she took from it is usually a real one.
What time of day are you at your best, and what time should nobody ask you for anything?
Why ask it
It asks for both ends of her day instead of a morning-person label. Practical too: you find out when she will enjoy a call and when she will merely survive it.
What tradition with your family or friends would you never skip?
Why ask it
Traditions show who she makes time for, whether it is an annual camping trip or a standing Sunday call. How she talks about this one tells you what belonging looks like to her.
What's the most spontaneous thing you've done in the past year?
Why ask it
For some people the answer is a last-minute flight and for others it is ordering a different sandwich. Both are fine. You are finding out how she feels about plans, and whether yours will need an itinerary.
What have you been putting off because it would be more fun with a second person?
Why ask it
Easy to answer, because the obstacle is company and not courage: a pub quiz, a tandem kayak, a beginners' dance class. If it is something you would enjoy too, do not pounce. Just remember it.
To get to know her
What's the best thing that's happened to you this year so far?
Why ask it
It starts her on good news, which is a kinder place to begin than work or the weather. Whether she says a new job, a puppy or one very good Tuesday, you learn what counts as a win to her.
What are you unreasonably good at that almost never comes up?
Why ask it
Folding a fitted sheet, peeling an orange in one piece, guessing what a house sold for. A talent with no stage is fun to boast about because nothing is riding on it. Ask for a demonstration only if one is possible where you are sitting.
Is there a story behind anything you're wearing or carrying today?
Why ask it
It works because you noticed something specific and asked about it, which reads as attention and not as a line. A ring that was her grandmother's, a keyring from a trip, a jacket rescued from a market stall. If the answer is 'it was on sale', laugh and move on.
Where do you go when you want to get out of the house but have nowhere you need to be?
Why ask it
Everyone has a place like this and few people get asked about it: a library table by the window, the long way round the park, a cafe where nobody hurries her. Being told is a small compliment. Do not turn up there unannounced.
What were you known for at school, and was it fair?
Why ask it
Most people think their school reputation missed something, so 'was it fair' is where it gets interesting. She might have been the loud one, the sporty one or the girl always drawing in the margins. If she is still at school, ask what she expects to be remembered for.
What's something about your average weekday that nobody would guess?
Why ask it
Every job, course and team has a side that outsiders do not see: the nurse buried in paperwork, the barista refereeing the morning rush. She gets to talk about her days without reciting a title, and you find out what she finds absurd about them.
What have you taught yourself from scratch, and how long did it take to stop being bad at it?
Why ask it
Cutting her own bangs, fixing a bike, three chords on a guitar, a language from an app. Asking how long she was bad at it invites the comedy of the early attempts. Teaching yourself anything takes some stubbornness, and this is how you hear about hers.
What book, film or album do you wish you could go through again for the first time?
Why ask it
Easier to answer than 'what's your favorite', because she only has to pick the one that surprised her. Do not announce that you already know how it ends. Ask what it was like not knowing.
What smell takes you straight back somewhere, and where does it take you?
Why ask it
A direct question about her childhood gets a summary. This one gets a scene, with the weather and who else was there: sunscreen and one particular beach, chlorine and Saturday swimming lessons, the hallway of a relative's house.
What's your favorite room in any place you've ever lived?
Why ask it
A room is easier to describe than a whole childhood, and she usually ends up telling you who else was in it. A kitchen with a window seat, an attic bedroom, the tiny balcony of a first apartment. Ask what she did there.
Who's your oldest friend, and what were the two of you like when you met?
Why ask it
The meeting is usually a good story: a seating chart, a shared enemy, a fight over a swing. How she talks about someone who has known every version of her tells you how she keeps people.
What small luxury would you never give up?
Why ask it
Good coffee, fresh sheets, the window seat, the nice olive oil. It is a small preference she has thought about, so it is easy to talk about and worth remembering when you choose where to meet.
What part of your routine is not up for negotiation?
Why ask it
You learn what keeps her steady, and which hour of her day to leave alone. It might be the same walk every morning, tea before she speaks to anyone, or Sunday night spent setting up the week.
Which of your teachers would be least surprised by how you turned out, and which would be most?
Why ask it
A teacher watched her for a year at an age she can barely remember being, and usually made a prediction. Whether she proved it right or wrong, she gets to measure herself against it out loud. If she is still at school, ask which teacher has her figured out.
What would you do with a year off and nobody to explain it to?
Why ask it
No career logic, no relatives asking what it is for. Some people would travel, some would build something, and some would sleep until March and then decide. Her answer shows what she would do if nobody were keeping score.
What are you working toward at the moment, big or small?
Why ask it
'Big or small' matters, because it lets a driving test or a tidy bedroom count as much as a degree. Ask how it is going, then ask again in a few weeks. The follow-up is the part she will remember.
What are you looking forward to that's more than a year away?
Why ask it
Most small talk lives in this week, so a question about the far future is a pleasant surprise. A graduation, a move, a trip that is still only a savings jar. You also see how far ahead she likes to look.
What question do you wish people asked you more often?
Why ask it
A shortcut to whatever she most wants to talk about, whether that is her painting, her dog or the book she is halfway through writing. Ask it straight away. Then remember that you are now one of the people who asks.
What's the earliest memory you're sure is your own and not from a photo?
Why ask it
Most people have a few early memories that turn out to be a photograph, or a story told so often it feels remembered. The real one tends to be small and odd: a pattern on a carpet, being lifted up to see over a wall. Ask how she knows it is hers.
Who has one thing in their life that you'd happily steal, and what is it?
Why ask it
Not a hero to worship, only one thing worth borrowing: an aunt's garden, a friend's nerve, a cousin's knack for leaving a party on time. Envy described this cheerfully is really a list of what she wants.
What's your family like when you're all in one room?
Why ask it
A scene is easier to describe than a verdict, so she can tell you it is loud, careful or competitive over board games without having to judge anyone. You also hear where she sits in it. If home is complicated, a short answer is still an answer.
What did the people who raised you get completely right?
Why ask it
Starting from what went right keeps a family question warm without pretending everything did. Bedtime stories, being trusted with a key early, a firm rule about thank-you notes. Often it is the thing she plans to repeat one day.
What do you miss about being a kid?
Why ask it
Long summers, being carried in from the car, somebody else deciding what was for dinner. It is nostalgia without the weight, and what she misses is often what she is short of now.
What do you appreciate about where you grew up now that you didn't back then?
Why ask it
People are often funny and fond about the place that bored them at fifteen: knowing every neighbor, the bus that came twice a day, the quiet she could not wait to leave. It works whether she moved across the world or still lives on the same street.
People and pets are already safe: what's the one object you'd go back for?
Why ask it
Ruling out people and pets removes the obvious answer and leaves the sentimental one. A box of letters, a childhood bear, a hard drive of photos. Ask where it came from.
What makes you nervous that other people seem to find easy?
Why ask it
A small fear is easy to admit when the question assumes everybody has one, be it phone calls, ordering at a counter or walking into a room where everyone already knows each other. Offer yours, and never tell her that hers is silly.
How can someone tell you're stressed before you say so?
Why ask it
Some people go quiet, some start cleaning, some get very polite. It is a personal question with a practical use: you are asking for the early signs so you can be kind in time. It is fine to say so.
Who do you go to when you've had a bad day, and what do they get right?
Why ask it
What that person gets right is what she wants when a day goes badly, so listen to that part closely. It might be a sister who lets her rant, or a friend who turns up with snacks and no advice. If the answer is her dog, the dog is doing something right too.
What's the bravest thing you've ever done?
Why ask it
Brave is hers to define. It might be a solo trip or a stage, and it might be a hard conversation or walking out of something that looked fine from outside. Do not rank it against yours.
What are you most short of at the moment: time, sleep, company or quiet?
Why ask it
Four options make a personal question quick to answer, and the one she picks tells you what kind of month she is having. Listen without rushing to supply it. The exception is quiet, which you can give her on the spot.
Funny
What would your friends ban you from doing if they could?
Why ask it
Seeing herself through her friends' eyes makes the roast gentler, and the answers come fast: karaoke, giving directions, telling that one story again. Consider it fair warning.
What are you convinced you'd be great at despite having zero evidence?
Why ask it
Landing a plane in an emergency, curling, naming racehorses, solving a murder on a train. Silly enough that there is no wrong answer, and the unearned confidence is the joke. Offer yours and argue about whose is less likely.
What's your worst impression, and are you willing to do it right now?
Why ask it
Best in person and only once she is already laughing. If she commits to a terrible accent in front of you, things are going well. If she declines, do yours first and lower the bar.
What unlikely situation do you have a suspiciously detailed plan for?
Why ask it
Most people have one, for a lottery win, a zombie outbreak or meeting one particular celebrity in an elevator. It costs her nothing to tell, and the level of detail shows what her mind gets up to when it is idling.
What dance move do you fall back on at weddings, and how would you rate it honestly?
Why ask it
Asking her to rate it turns a quiz into a story, usually one with witnesses. A willingness to describe her own bad dancing suggests she does not take herself too seriously.
What would your job have been in a medieval village, realistically?
Why ask it
'Realistically' rules out queen and forces a funnier answer: village gossip, anxious baker, person who is simply very good with goats. Offer your own humbling answer in exchange.
What's the worst date idea you can invent in the next ten seconds?
Why ask it
A shared joke about bad dates makes the idea of a good one less loaded. Build on hers instead of topping it, and you are writing a bit together, which is its own kind of flirting.
What's an activity everyone seems to love that you simply do not get?
Why ask it
Brunch lines, camping, escape rooms. Complaining cheerfully about something harmless is bonding, and you would rather learn she hates camping now than halfway up a trail.
What rule have you made up for yourself that makes no sense to anyone else?
Why ask it
Private logic is endearing: the volume only on even numbers, never the front item on a shelf, one lucky exam pen. She will enjoy explaining hers, provided you ask out of interest and do not mock it.
What movie or book have you pretended to know for so long that it's too late to confess?
Why ask it
A confession with no real stakes, which makes it a good way to practice being honest with each other. Promise to keep the secret, and then keep it, including in front of her friends.
How far have you gone to avoid someone you know in public?
Why ask it
Funny because everyone has done it, whether that meant faking a phone call or hiding behind a cereal display. It lets her admit to being awkward without calling herself awkward.
Which of your friends would last longest in a horror movie, and where would you rank?
Why ask it
She ends up describing her whole friend group by survival skills, which is a lively way to meet them in advance. Her own ranking shows whether she sees herself as the planner or the one who trips.
What do you do when you're home alone that would be hard to explain to a visitor?
Why ask it
Keep your tone light, so it is clear you are after the goofy answer and nothing more: narrating her cooking like a TV host, full concerts for the cat, arguing with a podcast.
What's the worst advice you've ever actually followed?
Why ask it
The word 'actually' is where the comedy is: someone said it, and she did it. A group costume, a shortcut through a field, reading only the summary. You also learn whose advice she no longer takes.
What would your reality show be called, and why would it get cancelled?
Why ask it
The title shows how she sees her own life, and the cancellation reason is where she roasts herself. 'Nothing happens and she is asleep by ten' is a perfectly respectable answer.
If you came back as a ghost, who would you haunt, and how petty would it be?
Why ask it
Pettiness is the point: moving a former roommate's keys two inches a day, forever. It lets her air a small grudge as comedy, and you find out how long her memory is.
If your pet, or one you grew up with, could talk, what would it tell everyone about you?
Why ask it
Pets have seen everything: the pep talks in the mirror, the second dinner, the crying at commercials. She gets to confess through a witness, and a witness that adores her at that.
What word did you mispronounce for years before anyone corrected you?
Why ask it
It is usually a word she met in a book before she ever heard it aloud, so the mistake is to her credit. The comedy is in how long it lasted and who finally said something. Admit yours, because everybody has one.
What do you eat in a way that other people find upsetting?
Why ask it
Mock outrage is the correct response to pizza eaten crust first, or a chocolate bar bitten straight across all four fingers. It is a rare argument in which nobody can be wrong and nobody will back down.
What kind of passenger are you: navigator, DJ, backseat driver or asleep in four minutes?
Why ask it
Four options, and most people know at once which they are and which their friends would say. Her answer is also worth having before any trip longer than twenty minutes.
Which game turns you into someone your friends don't recognize?
Why ask it
Competitive rage over something that does not matter is very funny from the outside, and the culprit tends to be Monopoly, a kart racer or charades with her family. Suggest a rematch only if you are prepared to lose well.
What tiny, pointless hill are you prepared to die on?
Why ask it
An argument about nothing is a safe way to find out how she argues. She might insist that a hot dog is not a sandwich, or that one film is plainly better than its sequel. Take the other side for exactly one round, then concede.
What's the least impressive thing you've ever bragged about?
Why ask it
A third grade spelling prize, a wave from a minor celebrity, finishing a large jar of pickles alone. A brag that small is really a joke at her own expense, which is the easiest kind to make with someone new.
What do you do badly on purpose so nobody asks you to do it again?
Why ask it
Strategic incompetence is a confession most people enjoy making. Loading the dishwasher, wrapping presents, reading the map: remember what she says, because it is also a list of jobs she will happily leave to someone else.
Who was responsible for the worst haircut you've ever had?
Why ask it
Asking who did it lets her blame a sibling with scissors, a brave salon decision or herself at midnight. If photos exist she will mention them. Whether you get to see one is up to her.
What's the strangest compliment you've ever been given?
Why ask it
'You have very trustworthy elbows.' 'You remind me of my aunt, in a good way.' An odd compliment sticks for years because nobody knows what to do with it, and repeating it lets her say something nice about herself without boasting.
Which gift did you have to pretend to love, and how good was the performance?
Why ask it
The acting is the story: the face she made, how long the thing had to stay on display. A sweater two sizes off, a self-help book, a framed photo of the giver. Take note of what not to buy.
What are you known for in your family's group chat?
Why ask it
A family chat is a small sitcom, and her part in it sketches the whole cast. She might be the one who replies with a thumbs-up three days late, or the keeper of the unflattering photos.
When have you been completely confident and completely wrong?
Why ask it
Directions given with authority, a quiz answer shouted too early, a wave returned to someone who was waving at the person behind her. Certainty followed by a fall is the whole shape of a joke, and she is the one telling it.
What's the most dramatic thing you did as a kid to get your own way?
Why ask it
Small children commit to a bit like nobody else: running away as far as the garden gate, a hunger strike that lasted until dessert, a written list of demands. She gets to laugh at herself from a safe distance of many years.
What small injustice from childhood are you still not over?
Why ask it
Told with mock bitterness, a very old grievance is funny: the sibling who always got the front seat, the school play part that went to someone else. She will want to hear yours.
What story does your family tell about you every time there's a new audience?
Why ask it
She will groan and tell it anyway, whether it is the wedding she slept through under a table or the thing she said to a neighbor when she was four. You are the new audience now, so laugh in the right places.
What was your most regrettable phase, and does any evidence survive?
Why ask it
Save it until you have both been laughing for a while, since it asks her to hand you ammunition. The right response to the evidence is delight, never teasing that outlasts the evening.
What has a parent done in public that made you want to disappear?
Why ask it
Everyone's parents have done something, from loud singing in a store to befriending her teachers. The way she tells it, with affection or a wince, is a gentle preview of how she feels about home.
What's the worst way you've ever tried to look cool in front of a crush?
Why ask it
The closest the Funny group gets to flirting. Trade stories evenly here: if she admits to pretending she liked a band for a year, you owe her something equally undignified.
Flirty
Slow dancing in the kitchen with no music on: sweet or unbearable?
Why ask it
An either-or that sorts the romantics from the eye-rollers in one line. Neither answer is bad news. It just tells you whether your gestures should be sincere or delivered with a wink.
Who would win a staring contest between us, and why are you so sure?
Why ask it
An invitation to hold eye contact disguised as a competition. If she wants to settle it on the spot, win or lose as you like, but laugh when it ends. The laughing is the point.
What romantic movie move would actually alarm you in real life?
Why ask it
Showing up uninvited, the airport chase, not taking no for an answer. It is funny, and it also tells you plainly where her line sits between romantic and too much. Take notes.
What do you wear on the days you feel your absolute best?
Why ask it
Asks how she feels, not how she looks, which is a better compliment than most compliments. If you later notice she is wearing it, say so, once and simply.
Do you like being teased a little, or should I retire that plan now?
Why ask it
Checking before you tease is both considerate and, oddly, flirtier than just doing it. Some people love banter and some hear it as criticism. Believe whichever answer she gives.
Are you a hand-holder right away, or does that take a while?
Why ask it
About as innocent as flirting gets, and it lets her tell you her pace without a serious talk. Whatever she says, follow it. Asking and then ignoring the answer is worse than not asking.
What's your idea of being spoiled: breakfast made for you, a day planned, or being left alone with a book?
Why ask it
Three options make it easy, and the third is there on purpose. Plenty of people feel most cared for when someone protects their quiet, and they rarely get asked.
What's a photo of yourself that you love, and what was going on when it was taken?
Why ask it
People love photos where they were happy, not only ones where they looked good, so the story tells you what happy looks like for her. Do not ask to see it. Let her offer.
Which is more attractive: someone who makes you laugh, or someone who laughs at your jokes?
Why ask it
It tells you whether to bring your best material or be her best audience, and most people know their answer at once. If she says both, ask which one she would give up first.
Which cartoon character did you have a completely serious crush on as a kid?
Why ask it
The more solemn she was about a cartoon fox or a prince at seven, the better the story. It is flirting at its most harmless: you get to talk about crushes without anyone admitting to a current one.
Coffee, a long walk or something where we both look ridiculous: which would you pick for a first date?
Why ask it
It shows you have thought about a date without having booked anything. The ridiculous option is there for people who would sooner bowl badly than make conversation across a table. Whichever she picks, that is your plan.
Would you rather be serenaded badly or handed a terrible poem?
Why ask it
Both are awful and both are sweet, which is the joke. Someone who picks the serenade can stand a scene, and someone who picks the poem would like to keep it private. Do not offer a sample unless she asks twice.
Which is the most romantic weather: rain on the window, first snow or a warm evening that won't end?
Why ask it
There is no wrong answer, only a forecast. Rain people want to stay in, snow people want to go out and look, and warm-evening people do not want to go home. Note which, and plan for the season.
Who should text first after a good date: the one who asked, or the one who had the better time?
Why ask it
A playful debate with a practical answer hiding in it. Whatever rule she invents, she has told you what she would like to happen and how long is too long to wait.
When someone flirts with you, do you notice straight away or three days later?
Why ask it
Plenty of people only work it out on the way home, or when a friend points it out. If she says she never notices, take that as a request to be clearer and kinder, not louder.
What do you do when you like someone that gives you away?
Why ask it
Talking too fast, going quiet, laughing before the joke is finished, suddenly having opinions about their favorite band. She is handing you a field guide, so try not to study her too obviously while she answers.
What kind of message makes you smile at your phone?
Why ask it
You are asking what it feels like to be thought of, and the answer is rarely anything clever. A photo of a dog, 'saw this and thought of you', a plain 'home safe?'. Send that kind, and not ten of them at once.
What nickname would you put up with, and which one would end this conversation?
Why ask it
The banned one is the better story, usually something a brother or a coach started. Promise never to use it and keep the promise. If she names one she likes, let it come up on its own before you try it.
What's the smallest thing someone has done that made you think they'd really been listening?
Why ask it
Remembering how she takes her coffee, asking how the thing on Thursday went. More fun than asking about red flags, and more useful. Whatever she names, resist performing it in the next five minutes, because she will notice.
What makes you lose interest in someone almost instantly?
Why ask it
Ask with a grin and treat the answer as the gift it is: a short list of things never to do in front of her. Rudeness to staff and people who talk only about themselves tend to be on it.
What's the most romantic thing you've ever watched one ordinary person do for another?
Why ask it
Often it is something small: a grandfather who still opens the car door, a friend's partner who learned her favorite recipe. It tells you what she counts as romance, which is rarely grand.
What's a date you've always wanted to go on that nobody has ever planned?
Why ask it
You will rarely be handed a clearer hint. Do not announce that you are going to plan it. Wait a couple of weeks, then plan it.
When did you last get butterflies, and what caused them?
Why ask it
If the answer is a job interview, laugh and move on. If she looks at you and hesitates before answering, you may not need the rest of this list.
What would you change about the way people usually ask you out?
Why ask it
Many people are tired of the vague 'we should hang out sometime' and would prefer a clear plan with a day attached. Whatever she says, you have been handed the instructions.
What's the one detail a person planning your birthday would have to get right?
Why ask it
No surprises, the right cake, her sister being there. It is flirty because it imagines you still around on her birthday, and practical because now you know what matters.
How gracious a loser are you, and should I let you win at mini golf?
Why ask it
A challenge and an invitation in one sentence. The right answer from her is some version of 'you could not beat me if you tried', and then you have a plan for Saturday. Never actually let her win, because she will know.
If we were a team at a trivia night, which rounds would be yours and which would be mine?
Why ask it
She has to guess what you know, which shows how much she has been listening, and claim her own ground, which shows what she is proud of. Being a team for one imaginary evening is a low-risk way to try the idea out.
What would you let me teach you, and what would you insist on teaching me?
Why ask it
A trade keeps it even: nobody is the expert and nobody is the project. It might be a card trick for a pancake recipe, or a tennis serve for how to change a tire. Either way you have invented two reasons to meet.
If I planned a whole day for you, what would I definitely get wrong?
Why ask it
She gets to tease you in advance, and under the teasing is real information: too early a start, too many people, a restaurant with shared tables. Thank her for the warnings and use them.
Honest opinion: which of us is worse at flirting?
Why ask it
Admitting that you are both doing it, and doing it badly, takes the pressure off faster than a smooth line would. If she says it is you, agree at once. Agreeing is, annoyingly, quite good flirting.
Is it a date if nobody calls it a date?
Why ask it
Half joke and half real question, best asked with a smile somewhere that could plausibly be one. If she laughs and says it depends who is asking, you have your answer. If she says no, you have a clear one, and you stay friendly.
What's one small habit of mine that you've already picked up on?
Why ask it
Interested people notice things: how you stir your coffee, the word you overuse, the way you check for your keys. If she has an answer ready, she has been watching. If she needs a minute, enjoy the minute.
What would your best friend need to see from me before signing off?
Why ask it
A playful way to acknowledge that a review panel exists. Her answer describes what her friends have watched her go through before, so listen to the serious part inside the joke.
What quality are you quietly hoping I turn out to have?
Why ask it
Bold, so save it for when things are clearly going well. It asks what she wants without asking her to rate you, and you should answer honestly about whether you have it.
What's your favorite thing about me so far? And can I have it in writing?
Why ask it
Fishing for a compliment only works when you admit that is what you are doing, hence the second line. Return the favor immediately and make yours more specific than hers.
Deep
What's something people assume about you that's flat wrong?
Why ask it
Quiet people get read as cold, cheerful people as shallow, organized people as never struggling. She gets to correct the record, and you get to check which assumptions you had made yourself.
What does 'home' mean to you: a place, a person or a feeling?
Why ask it
The three options stop it from being too abstract to answer. People who moved a lot, or whose family home is complicated, often have the most considered answers, so give her time.
What's the most grown-up thing you've had to do that nobody prepared you for?
Why ask it
Rarely anything on the official list of milestones. More often a first lease signed alone, a hospital waiting room, or the day a parent asked her for advice. It is a soft way to reach a serious story, and she can keep it as light as a tax form if she wants to.
What advice would you give yourself at sixteen that you definitely would have ignored?
Why ask it
The 'would have ignored' keeps it rueful instead of preachy. What she picks is usually the lesson that cost her the most, told with enough distance to be comfortable.
Who outside your family did something for you that you only understood years later?
Why ask it
It turns the conversation toward what she was given and away from what she achieved, and people tend to soften when they talk about that. Expect a teacher who kept her back after class, a first boss who said no, or a neighbor who always seemed to have dinner to spare.
What's the best decision you ever made that everyone advised against?
Why ask it
It shows how she weighs her own judgment against other people's. The decision might be changing majors, moving away or ending something that looked fine on paper. Ask whether anyone has since admitted she was right.
What have you outgrown that you still sometimes miss?
Why ask it
A friend group, a city, a version of herself who stayed out later. It lets her be wistful without being sad, and shows she can leave something behind without pretending it was worthless.
What's the best thing about being the age you are right now?
Why ask it
A deep question that starts from contentment, which is rare. At seventeen it might be the freedom of a first car, at thirty no longer caring what a certain crowd thinks. It asks her to notice what is good now instead of what comes next.
What memory do you go back to when you need to feel better?
Why ask it
You are being shown the place she feels safest, so take the tour quietly. A kitchen table, a lake, the back seat on a night drive with someone else at the wheel. Ask what it sounded like.
When did you last change your mind about something that mattered?
Why ask it
It shows how she handles having been wrong: who or what persuaded her, and how long she held out. It need not be a belief. Deciding she had misjudged a person, a city or her own plans counts just as much.
What small moment do you think about more often than it deserves?
Why ask it
Something a stranger said on a train, a look from a teacher, an afternoon when nothing happened. There is usually no neat reason it stuck, which is what makes it worth hearing. Do not interpret it for her.
What do you want an ordinary Tuesday to look like ten years from now?
Why ask it
The Tuesday is the trick. Anyone can describe a dream job or a wedding, but an ordinary weekday needs a kitchen, a commute and somebody at the table. Listen for who is in the picture and how fast the day moves.
What part of the future are you excited about, and what part scares you?
Why ask it
Two halves, so she does not have to pretend to be either fearless or doomed. Often the same thing turns up in both: moving away, a career, having a family. Say which of yours match.
What do you think you'll care about at eighty that you barely think about now?
Why ask it
A question about values that comes in from the side, and it is hard to answer cynically. She may say old friends, a garden, or having been kind. If she says 'my knees', she is right about that too.
What did a friend once say to you that you've never forgotten?
Why ask it
Sometimes it was a rescue and sometimes a hard truth: 'you are allowed to leave', 'you were unkind and you know it'. You learn what she needed to hear at some point, and which friend had the nerve to say it.
What do you believe that most of your friends don't?
Why ask it
It does not need to be politics. It could be about money, marriage, staying in one town, or whether people are basically good. You are really asking how it feels to be the odd one out among people she loves, so listen without casting your vote.
What role do you play in your family, and did you choose it?
Why ask it
Peacemaker, organizer, the funny one, the one who moved away. Whether she chose it is the real question. Plenty of people were assigned a part at twelve and have been quietly tired of it since.
What's a compliment you have trouble believing?
Why ask it
Whatever she names is the thing she most wants to be true. Do not rush to insist that it is. Ask why it is hard to take in, and listen to the answer all the way through.
What do you do when you're lonely?
Why ask it
Assumes, correctly, that everyone sometimes is, which makes it easier to answer than 'do you get lonely'. Some people call someone, some clean the kitchen. There is nothing for you to fix here, only something to know.
What makes you feel taken for granted?
Why ask it
Worth asking before it ever applies to you. Being the one who always plans, never being thanked, having her time treated as flexible: whatever it is, you can decide now not to do it.
What do you want to be true about the way you treat people?
Why ask it
Phrased as an aim, not a claim, so she does not have to pretend she always manages it. The value she names is likely the one she will expect from you in return.
What boundary did you have to learn to set the hard way?
Why ask it
There is a story behind this and it may not be a happy one, so let her choose how much of it to tell. What matters is that you now know the boundary exists. Respect it without being reminded.
What dream did you quietly put down, and do you ever think about picking it back up?
Why ask it
Asking whether she would pick it back up turns a regret into a possibility, whether the dream was a band, a business idea or a sport she was good at. Her face will tell you if it is truly finished.
What do you know about love now that you wish someone had told you earlier?
Why ask it
Invites the lesson without requiring the story of who taught it, so there is no need to discuss an ex by name. Hold your own answer ready. This one should go both ways.
What part of you takes people the longest to see?
Why ask it
A kinder way of asking what she hides. It may be a temper, a silly streak, or how much she worries. Hearing about it early is a privilege, so do not go looking for it on the next date.
How do you know when someone really cares about you?
Why ask it
Asked this way it gets evidence in place of theory: they turn up when it is inconvenient, they tell her the truth, they ask a second question. Some people need to hear it said and some trust only what is done. Notice which she is.
What did you have to learn to like about yourself?
Why ask it
Her laugh, her height, being the serious one, needing more time alone than her friends do. The wording has a happy ending built in, which makes a tender subject easier to open. Skip telling her you liked it all along, and ask what changed her mind.
What do people expect of you that you'd love a week off from?
Why ask it
One week is a small enough wish to say out loud, even for someone who is always the reliable one, or the daughter who never causes worry. You cannot lift it for her, but you can avoid adding to it.
What do you worry about that you rarely say out loud?
Why ask it
She may hand you a small worry first to see what you do with it: money, a parent's health, whether she picked the right path, friends who seem to be moving faster. Do not solve it. Tell her it makes sense.
What hard stretch are you proud of having come through?
Why ask it
It lets her name a hard time by its ending and say as little about the middle as she likes. A bad school year, an illness, a move she never wanted. Being proud of getting through is not the same as being over it, so follow her tone.
Who do you miss that you could still call?
Why ask it
'Could still call' keeps the question on people she can reach and turns it toward something she can act on. A friend from an old job, a cousin, a grandparent two time zones away. If she goes quiet, she may be composing the message, so let her.
Is there something you keep meaning to say to someone and haven't?
Why ask it
A thank-you, an apology, 'I am not actually fine with that'. Unsaid things take up room, and saying one aloud to somebody uninvolved is often the rehearsal it needed. Bring it up again only if she does.
Which friendship ended in a way you still think about?
Why ask it
Often it was no fight at all: a slow fade, a move, one message left unanswered until it was too late to answer. A lost friendship gets asked about far less than a breakup, so she may not have told this one often. Do not take sides in a story you heard half of.
What's an argument you handled badly, and what would you do differently now?
Why ask it
How she tells it shows whether she faces conflict or waits for it to pass, and what she would change shows what she took from it. Ask only when the evening can hold it, and have your own slammed door or midnight message ready to trade.
What moment split your life into a before and an after?
Why ask it
The heaviest question here, and not one for a first date. If she answers, your only job is to listen and thank her. Do not match it with your own story unless she asks.
Over text
What are you having for dinner, and is it a proud dinner or a survival dinner?
Why ask it
The proud-or-survival split is what makes it answerable with a laugh. Cereal over the sink gets a better conversation going than any elaborate recipe, so be ready to confess yours.
What's your phone battery at right now, and what does that say about you as a person?
Why ask it
A ten-second answer that reliably divides the world into the always-charged and the permanently in the red. It works best typed, and it tells her you are fun to message, not just persistent.
What's the plan tonight: going out, staying in, or pretending you might go out and then staying in?
Why ask it
The third option is the honest one for most people, and naming it shows you will not judge a quiet night. Multiple choice is kind over text: she can reply with one word and still be charming.
What's your most-used emoji lately, and what does it say about your week?
Why ask it
She can check in a second, which is what a good text question allows. The crying-laughing face and the melting face describe very different weeks, and both give you something to ask about.
What are your top three breakfast foods, ranked, knowing that I will be judging?
Why ask it
Ranked lists are made for texting: quick to type, easy to argue with. The announced judging sets a teasing tone that plain text would otherwise lose. Disagree with exactly one item.
Mountains at sunrise or a city at midnight: which one, and how will you defend it?
Why ask it
An either-or is the lowest-effort reply there is, and asking for a defense turns one word into a paragraph. It also sketches the kind of trip, and the kind of hours, she likes.
What's the most boring thing that happened to you today, completely unedited?
Why ask it
Asking for the dull parts takes away the pressure to be interesting by text. Oddly, the boring detail, the forgotten umbrella or the bus that never came, is usually where her personality shows up.
What's one thing you want to do this weekend, and one thing you have to do?
Why ask it
Two short answers and a clear picture of her week. If you are hoping to see her, the 'want to' half shows what kind of invitation would be welcome, and the 'have to' half shows when not to suggest it.
What's the last thing you screenshotted to send to a friend?
Why ask it
'To send to a friend' keeps it from feeling like a request to inspect her phone. Usually it is a joke, a product or an outrageous message, and explaining it means telling you about the friend too.
What tab has been open on your phone or laptop the longest?
Why ask it
A recipe she will never make, a flight she keeps pricing, an article from last spring. It is a confession with no downside, and she can check the real answer before replying.
If you could teleport somewhere for exactly one hour right now, where are you going?
Why ask it
The one-hour limit is what makes it interesting: nobody picks a far-off beach for an hour, they pick a person's kitchen or a particular bench. Works best sent in the dull middle of a weekday.
What's the best thing that could show up at your door in the next ten minutes?
Why ask it
It reads her mood without asking about her mood: takeout means tired, a best friend means a long week, a dog on loan could mean anything. If the answer is a specific food, you have learned something you can use.
How would a real estate listing describe the room you're in right now?
Why ask it
A small writing game, which suits a medium made of writing. 'Cozy, with original laundry pile' tells you where she is and that she is willing to play. Send yours back in the same style.
What do you send when you have no idea how to reply to something?
Why ask it
Everyone has a fallback: 'haha', a single emoji, a reaction and silence. Now you will recognize hers when it arrives, and you will know to change the subject instead of pushing.
Would you rather get one long message a day or lots of little ones all day?
Why ask it
Mismatched texting habits are an easy way to misread each other early on. Ask once, adjust, and neither of you has to guess what a quiet afternoon means.
If you texted your best friend right now, which three words would they use to describe you?
Why ask it
Texting gives her the option of really asking, and the screenshot of the friend's reply is often the best message of the week. It also gets you a character reference without requesting one.
Where do you stand on good morning texts: sweet, or too much?
Why ask it
Better to ask than to guess and either smother her or seem indifferent. Framed as a matter of opinion, it lets her set the level without having to turn down anything you have already sent.
Would you rather I sent you one terrible joke a day or one random fact?
Why ask it
Either answer signs you up for a daily delivery, so only ask if you mean to keep it up. A promised joke that never arrives is worse than no joke. One a day is also the limit, not the starting point.
Based on what you know about me so far, what's on the perfect sandwich you'd make me?
Why ask it
Played for laughs, but she can only answer from what she has picked up: that you hate tomatoes, that hot sauce goes on everything. A wildly wrong sandwich is just as good, because you get to correct it. Offer to build hers in return.
What's the most recent thing that reminded you of me?
Why ask it
Keep this one until you are fairly sure the answer is not 'nothing'. When it lands, you learn what she associates with you, and that you have been crossing her mind between messages.
How to ask so she wants to answer
Practical guidance for the conversation itself
Before you ask anything
Be curious, not strategic
None of these are lines, and she will be able to tell if you use them as if they were. Only ask a question when you want to know the answer. If you catch yourself planning your next question while she is talking, stop and listen.
Go first on the harder ones
With anything in Deep, and the personal questions that close To get to know her, offering your own answer first lowers the stakes. It shows the level of honesty you are asking for and proves you are willing to pay it yourself. Keep your answer short so the turn passes back to her quickly.
Let her set the depth
If she gives a Deep question a light answer, that is her telling you where she wants to be right now. Follow her there. Pushing past it rarely gets you a better answer and often costs you the next conversation.
Remember, then return
The most effective move has nothing to do with the list. Bring up something she told you last time: ask how the presentation went, or whether her sister's visit happened. Being remembered does more than any clever question.
Matching the tags to the setting
A first conversation in person
- 1Stick to Openers, the first half of To get to know her and the first half of Funny.
- 2Start with a comment on something in front of you both, and bring in a question from the list once you are already talking.
- 3Keep it short. Leaving while it is still going well beats staying until you run out.
- 4If it went well, say you enjoyed it and suggest a specific next time.
A first or second date
- 1Open with Funny to shake off the nerves on both sides.
- 2Use To get to know her for the middle of the evening: the interesting questions first, the personal ones once she is asking you things back.
- 3Move to the early Flirty questions once she is laughing and relaxed.
- 4Try one Deep question from the first half of that group, and answer it yourself as well.
- 5Leave the later Deep questions for when you know each other better.
Texting between dates
- 1Use Over text questions to keep things warm, not to get to know her entirely by phone.
- 2Match her rhythm. If she replies in the evening, do not send three messages at noon.
- 3Let some exchanges end. Not every thread needs another question on the end of it.
- 4When a text conversation gets good, use it to set up seeing each other.
What goes wrong, and what to do
Her answers get shorter
Short answers are information. She may be busy, tired or simply not enjoying the subject. Try one lighter question, and if the replies stay short, wrap up kindly. Do not ask whether something is wrong more than once.
You flirted too early
If a Flirty question gets a polite sidestep, do not repeat it louder. Say something easy like 'fair enough' and return to Openers or Funny. Whether flirting is welcome later will be obvious from her, not from how many times you try.
A question touched something sore
You will see it in her face, or in a long gap before a reply. Thank her for whatever she did say, tell her she does not need to go further, and change the subject yourself so she does not have to.
She asks nothing back
Give it a fair chance first: nerves make people forget their manners, and some need a few minutes to warm up. If the whole evening passes and she has not asked you a single thing, take it as an answer and be gracious about it.
You have run out of things to say
A silence usually feels longer to the person worrying about it. Take a breath and comment on something around you, or admit the pause with a smile. Grabbing another question off a list in a panic is what makes a quiet moment awkward.