Deep Questions to Ask a Girl
For anyone getting to know a girl they like who wants to get past small talk without turning it into an interview. The 99 deep questions to ask a girl here come in six groups: an easy way in, who she is, family and growing up, hopes and fears, love and relationships, and a group that works over text, gentlest first within each. Every question has a note on when to ask it, what her answer tends to show and what to say back.
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The questions
Each question, and why to ask it
Easing in
What's been on your mind the most this week?
Why ask it
A week is a small enough frame that she can answer with an exam, a friend or a song she cannot shake, and none of those is wrong. Follow whichever one she picks instead of steering toward something heavier. It is the safest first question on the page.
What do you do that makes you forget to check your phone?
Why ask it
Whatever swallows her attention is usually closer to what she loves than the hobby she would list if asked. It might be painting, a long drive or a conversation that runs until one in the morning. If it turns out to be a person, ask who.
What song means more to you than you could easily explain?
Why ask it
The story is usually in the place and the year more than in the lyrics, so find out where she was when it started to matter. Listen to it afterward and mention one thing you noticed, which lands better than saying you liked it.
What did you used to care about a lot that doesn't matter to you now?
Why ask it
It is a first step into how she has changed, taken from the comfortable distance of something already behind her, like being popular or what one particular person thought. What took its place is the follow-up, and usually the better half of the answer.
Do you like deep conversations, or do they wear you out?
Why ask it
You are asking permission before going further, and most people appreciate being asked. If she says they wear her out, stay in this group and keep the evening light. If she says she loves them, she has just invited the next question.
What's the best part of an ordinary day for you?
Why ask it
Her answer is often a stretch nobody else would notice, like the walk home or the ten minutes after the house goes quiet. Whether she spends it alone or with people says something about how she recharges. Have yours ready, because this one nearly always gets asked back.
What's the best compliment you've ever gotten that had nothing to do with how you look?
Why ask it
The exclusion is the point: it asks what else people have noticed about her. The one she remembers tells you which kind of praise means something to her. Do not use the moment to add a compliment of your own.
What's a tiny thing people do that instantly makes you like them?
Why ask it
Her answer is what she counts as good character, in a size small enough to spot on a first meeting. If it is holding a door or being nice to the person behind the counter, resist performing it in front of her five minutes later.
What do you do with a whole day that belongs only to you?
Why ask it
Some people fill a free day and some guard it empty. A day nobody else has a claim on shows her real pace, which a list of hobbies would not. Good early on, because there is no way to answer it badly.
Are you more comfortable in a big group or with one person at a time?
Why ask it
A practical question dressed as a personal one. If she is the one-person-at-a-time kind, the deeper groups on this page belong on a walk or in a quiet corner and not at a table of six. Say which you are, especially if it is the opposite.
What's your favorite way to spend time with someone: talking, doing something together, or just being in the same room?
Why ask it
Someone who picks the same room is telling you that silence with her is not a problem to fix. A talker will want the walk and the long phone call, and a doer would rather bake something or shoot hoops and let the talk happen on the side. Her answer also tells you where the rest of this page will go best.
What are you really into that your friends don't quite get?
Why ask it
Everybody has one interest they have stopped explaining, such as a sport nobody follows, a game or an era of history. She has probably not been asked for the long version in a while, so be the person who wants it. Tease the interest only if she teases it first.
What do you notice about people that most others miss?
Why ask it
Observant people light up at this one. She may say who has been left out of a circle, a laugh that is forced, or who has gone quiet, and whatever she names she is probably noticing about you too. Offer what you tend to pick up on and compare.
Do you make big decisions with your head or your gut?
Why ask it
Get the last big one as an example, because people often describe themselves one way and decide the other. Neither answer is the better one. You also find out whether she will want reasons or a feeling when the two of you have to choose something.
Who she is
Which three words would you pick for yourself, and which one would your friends argue with?
Why ask it
Three words alone get a list anyone could give. The word her friends would dispute is where she tells you how she sees herself against how she comes across. Offer your own three and let her do the arguing.
What are you proud of that never came with a grade or a trophy?
Why ask it
Taking away the official wins leaves the private ones: a friendship she repaired, a fear she walked through, a younger sibling she half raised. She may need a moment, since nobody hands out certificates for these. Do not fill the silence with suggestions.
What do you like best about the person you're turning into?
Why ask it
Harder to answer than it sounds, and many people deflect with a joke on the first try. Let the joke pass and wait. If she still cannot name one thing, tell her something you have noticed that is not about her appearance, and keep it to a sentence.
What about yourself are you still working on?
Why ask it
'Still working on' is kinder than asking for a flaw, because it assumes progress. Patience, speaking up and overthinking are common answers. Give yours too, honestly, and skip the urge to tell her she is fine as she is.
What's the one quality a close friend of yours has to have?
Why ask it
Loyalty, honesty and being able to laugh at themselves are the usual answers, and the reason behind hers is nearly always one specific person. 'Who has it?' is the follow-up. You are also hearing the standard that anyone close to her gets held to.
What's a piece of advice you actually live by?
Why ask it
The word 'actually' rules out the poster slogans and leaves the one line she really uses, which often came from a coach, an aunt or a friend's mom in passing. Who said it, and whether she believed it at the time, is the story. Trade the line you find yourself repeating to other people.
What won't you pretend to like just to fit in?
Why ask it
It shows how much fitting in is worth to her and where she stops paying for it, whether the thing is a band, a sport or a way of talking about other people. If it turns out to be something you love, take it well: she has just shown that she will be honest with you.
What do you know you're good at, even if you'd never say so out loud?
Why ask it
Plenty of people have been taught to play their strengths down, so the permission in the second half matters. Let her say it without making her qualify it. If you ever get the chance to watch her do the thing, take it.
Do you forgive easily, or do you hold on to things for a while?
Why ask it
Most people say 'it depends', so ask what it depends on: an apology, time, whether it was on purpose. There is no correct side. If she forgives fast, it is still worth checking now and then that she really is fine.
When something has gone wrong, do you talk about it right away or need to sit with it first?
Why ask it
Better learned now than guessed at later. If she needs to sit with it, a message that says 'here when you want me' and nothing more is the right size. If she talks right away, she usually wants to be listened to and not handed a list of fixes.
When did you last speak up when staying quiet would have been easier?
Why ask it
She might have defended a friend, corrected a teacher or told a group chat it had gone too far. How she tells it shows whether speaking up comes naturally or costs her something. If she says she stayed quiet and regrets it, respect the honesty and hold the advice.
What's the kindest thing you've done that hardly anyone knows about?
Why ask it
She may wave it away, since people who do things quietly are not used to reporting them. Ask once and accept a small answer. You are now one of the few who knows, so do not pass it on to her friends as a fun fact.
What issue do you care about more than most people around you do?
Why ask it
There is usually a moment behind it, such as a stray dog, a news story or the way a new kid got treated at school, and that moment is the better thing to ask about. You are there to understand it, not to debate it, even if you see it differently.
Do you think most people are good at heart?
Why ask it
A yes-or-no that nobody answers in one word. Her reasons tend to come from something she has seen, a stranger who returned a wallet or a friend who turned on her, so the opinion arrives with a story attached. If the two of you land on different sides, find out what would change her mind and say what would change yours.
Are you religious or spiritual at all, and has that changed as you've gotten older?
Why ask it
Faith shapes weekends, family and big decisions, so it is worth knowing, but only once the conversation is already comfortable. Listen the way you would to any other part of her life. This is not the place to argue for your own view, and a short answer means move on.
If you could fix one thing about the world, what would you pick first?
Why ask it
'First' makes her choose, and that is where her priorities show: something huge like hunger, or something close like how people talk to each other online. Then ask what she would do about it with one free afternoon. Big answers get interesting when they shrink to something doable.
What do people come to you for: advice, a laugh, a plan or someone to listen?
Why ask it
What people come to her for is how they see her, and it is not always how she would like to be seen. Ask whether she enjoys the job or got stuck with it. Then be honest about which of the four you tend to bring to her.
What do people expect from you because you're a girl that you'd like to hand back?
Why ask it
She will have a list, such as being the organized one, smiling on request or never being 'too much', and she may never have been asked for it. Do not argue with any item or explain it away. Hearing the whole list out is the entire job.
What are you grateful for now that you used to take for granted?
Why ask it
There is usually a reason she started noticing, and that reason is the story, whether the thing is a parent who drives her everywhere, good health or a friend who always picks up. It goes well after a heavier question, when the conversation could use something warm.
Family and growing up
What's the first thing someone should know about your family?
Why ask it
She picks the headline, so she decides how much to open: 'there are a lot of us', 'it is just me and my mom', 'we are loud'. Follow the thread she offers and leave alone whatever she left out. It is the easiest way into this group because there is no fact she is required to give.
Who in your family do you tell things to first?
Why ask it
That person's opinion will matter if the two of you get closer, so remember the name, whether it belongs to a mom, a sister or a cousin who is more like a friend. If the answer is nobody in the family, ask who she tells instead and leave the why alone.
Which family trip, holiday or weekend do you all still bring up?
Why ask it
Families keep a few stories on repeat, often the trip where everything went wrong. You get the whole cast in one scene, and you hear whether she tells it with affection or an eye-roll. It suits any kind of family, since even a small one has a legend.
What's a tradition in your family that outsiders would find strange?
Why ask it
Odd traditions get told with pride, and they show what her family is like when no guests are watching. A birthday breakfast rule, a song in the car, a holiday dish nobody else would touch. Trade one of yours, the stranger the better.
What did your house sound like when you were growing up?
Why ask it
An odd angle that gets a truer picture than 'what was your family like': a TV nobody was watching, brothers arguing over a controller, a radio in the kitchen, or real quiet. Listen for whether she misses the noise or was glad to get away from it. It also hints at how much hush she needs around her now.
Who did you want to be like when you were little?
Why ask it
Whether it was a cousin, a teacher, a singer or a cartoon character with a sword, the useful part is what she admired in them. Then find out how much of it she ended up with. More tends to have stuck than she expects.
Would you have been friends with the girl you were at twelve?
Why ask it
Most people wince first and then get fond. What she would warn that girl about and what she would tell her to keep are two different answers, and both are worth having. Admit what you were like at twelve before she has to ask.
Is there a friend from when you were little that you still wonder about?
Why ask it
Usually it is someone who moved away in third grade or landed at a different school, and the friendship never ended so much as stopped. The games the two of them made up show you what she was like at seven better than a direct question would. If she has ever looked that friend up, she will admit it a little sheepishly.
How have you changed the most since you were ten?
Why ask it
Ten is far enough back for the change to be clear and recent enough to remember well. Shy kids who got loud and loud kids who got careful both have a story about when it turned, and often a person who turned it. Trade your own before and after.
What did your parents trust you with early, and did you feel ready?
Why ask it
It gets at how she was raised from the proud side. A house key, a younger brother to watch or the bus across town alone all count, and whether she felt ready or was faking it is the part she will enjoy telling. Skip it if she has hinted that she had to grow up faster than she wanted.
What's the best story you've been told about your family from before you were born?
Why ask it
Every family has a few from before her time, like how her parents met or the year the house flooded, and she is the one who gets to tell it to you. Notice whether it comes out as a legend or as a warning. If nobody ever told her any, that is worth a moment too, and not a subject to push.
What's the best thing about your mom or dad as a person, apart from being your parent?
Why ask it
It asks her to look at a parent the way a stranger would, which most people have rarely tried. The answer is usually tender: she is funny with waiters, he fixes things for the whole street. Skip it if she has already hinted that home is complicated.
Was there a move, a new school or a change at home that shaped you more than people realize?
Why ask it
Ask only after a couple of easier family questions. A change like that often explains a lot, such as why she makes friends carefully or why she can talk to anyone. If nothing ever changed, that steadiness is its own answer and worth asking about.
Where do you and your family see things differently?
Why ask it
It could be her plans, her friends, faith, or how late is late. Hear her side without joining in against her parents, because agreeing too hard with a complaint about someone's family rarely goes well. A one-line answer means the subject is closed for today.
What's one thing from your childhood you'd want every kid to have?
Why ask it
Whatever she names, a backyard, cousins down the road, being read to every night, is the part of her own childhood she treasures most. Now and then the answer is something she went without, and she will make that clear if she wants you to know. It is a question about kids in general, so do not steer it toward plans.
Hopes and fears
What do you want to see with your own eyes at least once?
Why ask it
The lightest question in this group, which is why it comes first. Answers run from the northern lights to a band she has loved for years to a city from a film she watched too many times. Find out who she pictures standing next to her, and do not volunteer.
What do you want to be really good at one day?
Why ask it
Not a job title but a skill: surgery, the cello, putting people at ease. Ask how good she is now and she will usually tell you with a laugh. Checking on her progress a month later is worth more than the question was.
If you knew you couldn't fail, what would you try first?
Why ask it
Take failure away and the real wish comes out, whether that is auditioning, applying somewhere far away or starting something of her own. Ask what the smallest version of it would be. Do not tell her she should just do it.
Would you rather build a life close to home or somewhere nobody knows you yet?
Why ask it
Staying near family and starting over somewhere new are both strong wishes, and her pick shows how tied she is to this place. Some people want both at different ages, so let her say when. If your own answer differs from hers, say it anyway, since pretending to share a plan helps nobody.
What would make you feel like your life had gone well?
Why ask it
Bigger than a goal, so give her a minute. People answer with people, with work or with freedom, and it is worth noticing which comes first. Your own answer does not need to be finished to be worth sharing.
What does being happy look like for you: a few big moments, or a lot of good small ones?
Why ask it
The choice keeps a huge question answerable. Someone who says small ones will care more about a walk on a plain weekday than a grand surprise. An example of either kind from the last month makes it real.
How much pressure do you feel to have your future figured out, and where does it come from?
Why ask it
Most people feel some and assume they are the only one. It tends to come from parents, from classmates who seem certain, or from her own head at midnight. Skip the advice: saying you have not figured yours out either is the most useful thing you can add.
What do you feel behind on compared with other people your age?
Why ask it
Trade one of your own before she answers, so she is not the only one admitting something. Driving, dating, knowing what to study and having a group of friends all come up. Asked gently, it is a relief to say out loud.
What do you do to steady yourself before something that makes you nervous?
Why ask it
Most people have a trick, whether it is over-preparing, one particular playlist, a call to a sister or pretending to be someone braver. It lets her talk about nerves through what she does about them, which is easier than naming the fear. Remember the trick: before her next tryout or presentation you can remind her of it.
What scares you a little that you want to do anyway?
Why ask it
Fear and wanting in the same sentence is where the interesting plans are: a solo trip, a stage, moving out. It is lighter than asking for a fear outright. Ask what would have to be true for her to go ahead, and do not push her toward it.
What part of growing up are you least ready for?
Why ask it
Narrower than asking what scares her, and so easier to answer honestly: money, living alone, friends scattering, choosing one path over the others. Wait until the conversation is already honest. Say that it makes sense before you say anything else.
What good thing in your life did you not see coming?
Why ask it
It reminds both of you that plans are not the only way good things arrive. She might tell you about a friend she nearly did not sit next to or a move she fought, and the telling is usually happy. That makes it a good one to follow a question about what she fears.
Who do you worry about the most?
Why ask it
A fear pointed outward, toward a little brother, a grandparent or a friend who is having a rough year. The answer shows who she feels responsible for. There is nothing to fix here, so ask what that person is like.
What got you through the worst week you can remember?
Why ask it
It asks about what helped and not about what happened, so she can name a friend, a playlist or the dog without explaining the week itself. If she does explain, listen and leave the advice out. The next time she is having a bad one, you will know what to offer.
Is there anything you regret not doing when you had the chance?
Why ask it
Regrets about not doing are often gentler to tell than regrets about doing. A team she did not try out for or a goodbye she skipped is easier to say out loud than a mistake. If the chance still exists in some form, ask about it, and keep the encouragement light.
What's one thing about your life right now that you'd keep exactly as it is?
Why ask it
Most questions about the future assume she wants things to be different, and this one looks for what is already right: a friendship, a Sunday routine, her room. Ask it when a serious conversation needs a warmer turn.
If people remembered you for just one thing, what would you want it to be?
Why ask it
One thing is the hard part, and the choosing is what you are listening to: being kind, being funny, having made something. Ask how close she thinks she is, then answer for yourself without turning it into a speech.
Do you think you'll be a different person in ten years, or the same one with more experience?
Why ask it
Some people expect to be transformed and others expect to stay themselves, and each is a little afraid of the opposite. Ask which part of her she would bet on keeping. Nobody can be wrong about this yet, so it is a fair one to disagree on.
Love and relationships
What makes someone easy for you to talk to?
Why ask it
She is handing you instructions, so listen as if they were. Expect things like not interrupting and not turning everything into a joke. Skip asking whether you qualify and do what she listed.
What's a green flag you always notice in people?
Why ask it
More cheerful than asking for red flags, and it tells you more. She may say how someone talks about their mom, whether they apologize, or how they treat a friend who is not in the room. Where she learned to look for it is usually a story about one person.
Which fictional couple do you think actually has a good relationship?
Why ask it
Fiction is a safe distance from which to say what she wants. Plenty of famous screen couples are terrible to each other, so the pair she defends, and why, shows what she counts as being treated well. Argue for a couple of your own.
Do you think the best relationships start as friendships?
Why ask it
An opinion question, so she can answer without telling you anything about her own heart. Listen for how much she values knowing someone first. If she says yes, the patient route is the right one with her.
What does a good friend do that someone you're dating should do too?
Why ask it
It carries the standard she already holds for friends over to dating, where people sometimes forget it applies. Expect showing up, keeping a secret and being glad about her good news. Remember the list, because it is the one she will measure by.
What's romantic to you: a big gesture, or someone remembering the small things?
Why ask it
Flowers in front of everyone delight one person and mortify the next. Most people who pick small things can name one that somebody once remembered. Hear it as a fact about her, not a to-do list to act on by Friday.
Have you ever worked out your love language, and did the answer sound like you?
Why ask it
Either way you end up talking about whether she feels cared for through words, time, help or small gifts. If she thinks the whole idea is silly, that is a good conversation too. Say yours, and notice whether the two match or miss.
Do you think there's one right person for everybody, or lots of people it could work with?
Why ask it
Romantics and realists both have good arguments, and people enjoy making them. Her side shows whether she expects love to arrive or to be built. Disagree if you do, since a friendly argument here is half the fun.
What do you think love is mostly made of: a feeling, a choice or a habit?
Why ask it
It is phrased as an opinion, so she never has to say whether she has been in love. People who pick 'a feeling' tend to talk about how it starts, and people who pick 'a choice' about how it lasts. Give your own guess, and leave past relationships alone unless she brings one up.
Who earned your trust in a way you didn't expect, and what did they do?
Why ask it
A story is easier than a theory of trust, and it shows what counts with her. Maybe someone kept a thing to themselves, covered for her without being asked or admitted they were wrong first. Whatever that person did is the kind of thing to do, not to announce, and the opposite story, about who lost it, is hers to raise.
When someone says sorry to you, what makes it count?
Why ask it
Some people need the words, some need the behavior to change, and some only want it not to be made into a scene. It is easier to learn on a calm day than in the middle of a bad one. Tell her what works on you as well.
Is it easy for you to tell people what you need, or do you hope they'll guess?
Why ask it
Most people hope for guessing more than they admit, and she may laugh when she says so. Take it as a reason to ask her directly more often. It is not a weakness to point out.
How much time to yourself do you need, even from people you really like?
Why ask it
A lot, for some people, and it has nothing to do with how much they like you. Getting the answer now saves you from reading an unanswered message as a verdict. Give your own number honestly, even if it is 'almost none'.
How much does it matter to you what your friends think of someone you like?
Why ask it
For plenty of people the friends get a vote, and it is better to know that than to resent it. Ask what her friends tend to look for. Being decent to them matters for its own sake and not as a tactic.
What makes you feel respected by someone?
Why ask it
Whatever she lists, treat it as the minimum. Being listened to the first time and having a no accepted without a debate are the kind of thing that comes up. Ask it early and remember the answer for good.
What has a past friendship or relationship taught you about what you need?
Why ask it
Including friendships lets her answer without discussing an ex, and for many people a friendship is where the lesson came from anyway. Listen for the need and let the story stay as short as she makes it. Never ask for names.
What do you think people our age get wrong about relationships?
Why ask it
She has watched friends go through it, so these are her field notes: moving too fast, performing for an audience online, mistaking jealousy for caring. It is also a quiet way to find out what she would not want from you.
Do you think two people can go back to being friends after one of them has liked the other?
Why ask it
An opinion she will probably have evidence for, from her friends if not from her own life. It also shows how much she thinks a crush puts a friendship at risk. Ask it out of curiosity and not as a way of hinting at anything.
What do you want to stay true about you no matter who you end up with?
Why ask it
It asks what she is protecting: her friends, a sport, a plan to study far away, the right to be loud. Anyone who likes her should be glad that list exists. If you ever catch yourself wishing she would drop something on it, that is yours to fix and not hers.
Over text
What's one word for today, and what's behind the word?
Why ask it
One word is quick to type, and the second half does not let her stop at 'fine': 'long', 'weird' and 'loud' all come with a story. Reply to the story before you offer a word of your own. Send it only when you have time to read a long answer, because asking and then vanishing for three hours is worse than not asking.
What was the best five minutes of your day?
Why ask it
Even a bad day has five decent minutes, and looking for them is a kind thing to ask of someone. Send it in the evening, when the day is over. A reply about a snack or a dog on the street is a perfectly deep answer.
What song fits your mood right now? Send it and I'll listen.
Why ask it
A song says what a tired person does not feel like typing. The promise to listen is the important half, so keep it and reply with a line about the song itself. A sad one is not an emergency: ask whether she wants to talk or only wants company in the playlist.
What can you see from where you're sitting that you'd miss if it were gone?
Why ask it
It makes her look up from the phone and choose, whether that is the view from her window, a dog asleep on her feet or her mom's handwriting on the fridge. It only works by message, since in person you could look for yourself. Reply with the thing you can see from where you are.
Finish the sentence: 'I'm happiest when...'
Why ask it
A fill-in-the-blank suits a phone because the hard part, starting, is already done for her. Endings run from 'the food arrives' to something she has clearly thought about, and both deserve a real reply. Send your own ending first if you want a longer one back.
What are you proud of from this week that nobody noticed?
Why ask it
Small wins go unseen: an email she had been avoiding, a run in the rain, keeping her temper with a sibling. Typed out, it is easier to admit than it would be face to face. Notice it properly, in a full sentence and not an emoji.
Would you rather be completely understood by one person or liked a little by everyone?
Why ask it
An either-or she can answer in a word, with a reason that takes a paragraph. The first choice often comes from someone with one or two close friends, the second from someone who likes a full room. Put your pick in the same message so it reads as a trade.
Is it easier for you to say serious things in a message or face to face?
Why ask it
Ask before you send anything from the heavier groups. Some people find writing safer and some find a serious text cold. If she says face to face, keep the phone for the light ones and save the rest for when you see her.
What do you want more of in your life right now, and what do you want less of?
Why ask it
Two short lists are easy to type and say a lot: more sleep and less group chat drama, more time outside and fewer people asking about her plans. Answer both halves yourself in the same message. Leave her 'less' list alone unless she asks for ideas.
What won't your brain let go of tonight?
Why ask it
A late-evening text that makes overthinking sound like the normal thing it is. She may send one line or four paragraphs. Read it all, do not solve it, and tell her which part you would be stuck on too.
What do you believe late at night that you don't believe in the morning?
Why ask it
The usual candidates are that everything is ruined, that she should move abroad, or that she could still learn the piano. It is half a joke and half true, which suits a message sent late in the evening. At lunchtime it falls flat.
If you could send one text to yourself a year ago, what would it say?
Why ask it
A year is recent enough to be specific: 'do not take that class', 'she is not really your friend', 'it works out'. The message shows what the year cost her or gave her. Since it is already a text, ask her to write it word for word.
What's a question you keep turning over that you don't have an answer to yet?
Why ask it
It can be small, like whether to quit the team, or enormous, like what she wants to do with her life. You are not being asked to answer it for her. Send back the one you are stuck on, so the two of you are at least stuck together.
What's happening tomorrow that I should ask you about afterward?
Why ask it
Whether it is a test, a tryout or an awkward lunch, the point is the next evening, when you ask how it went without being reminded. That second message is the reason for the first one, and it is what tells her you were listening.
How to ask a deep question without making it heavy
Practical guidance for the conversation itself
Before you go deep
Earn the question first
A deep question out of nowhere feels like a test. Start with one or two from Easing in, and move on only when her answers are getting longer than your questions. If they are not, today is a light day, and that is fine.
Pay for every answer with one of your own
Each of these is a trade. If she tells you what she is afraid of and you nod and move to the next question, she has been interviewed. Answer the same question at about the same depth, keep it shorter than hers, and hand the turn back.
Two is plenty
The list is for choosing from, not for working through. Two deep questions with real follow-ups will carry an evening. Ten in a row turns a conversation into a form she is filling in, however good each one is.
What she tells you stays with you
Do not repeat her answers to your friends, screenshot them, or bring them back later as a joke or in an argument. She is deciding how much to trust you by watching what you do with the first small thing she shares.
Which group for which moment
A girl you like but barely know
Stay in Easing in and the first half of Who she is. Those questions are deep enough to show you are interested in more than her weekend and light enough that she can answer in a hallway or between classes. Leave Family and growing up and the fears for when she has started asking you things back.
Getting to know her over a few weeks
This is where Family and growing up and Hopes and fears belong. They go best side by side, on a walk, a bus or a long drive, where nobody has to hold eye contact while they think. Start each group near its top and go only as far down as the conversation wants.
Over text
The Over text group is written to be answered in a line or two, and evening is usually when people have room to think. Send one question, not three, and reply to what she writes before asking anything else. Never send a heavy question and then go quiet, and if a text conversation gets serious, offer to finish it in person.
When you are already close
Love and relationships is ordered from opinions anyone can give to questions about what she needs. The second half suits someone you have known for a while or are already dating. Ask them as questions about her, and resist steering each answer toward the two of you.
When it does not go to plan
She gives a one-line answer
Take it as the answer. She may be tired, in a crowd, or not ready for that subject with you yet. Go back to something lighter without commenting on it, and do not ask the same question again in different words.
She says she'd rather not say
Say 'no problem' and mean it, then change the subject yourself so she does not have to. How you take a no is the most important thing she learns about you in the whole conversation. Asking why, or asking again later, undoes it.
She tells you something heavy
Listen, thank her for telling you, and leave the fixing alone. Do not match it with a bigger story of your own. If it sounds like more than a friend can carry, it is fine to say you care and to ask whether there is an adult she trusts, such as a parent, a counselor or a doctor, who knows about it too.
It starts to feel like an interview
The sign is that you are asking and she is answering and nothing is coming back. Stop asking. Tell her something about yourself that she did not request, or let a silence sit, and see whether she picks the next subject.
She turns the question back on you
That is the best thing that can happen, so do not dodge it with a joke. Answer honestly and about as deeply as you hoped she would. If you would not answer a question yourself, it was not a fair one to ask her.