Personal Questions to Ask
For anyone who wants to know a friend, a crush, a boyfriend or girlfriend, or someone in the family better without prying. The 137 questions run from mild to close in six groups (Everyday, Growing up, Feelings, Relationships, Beliefs and Only if ready), so you can stop at whatever depth suits the two of you. Each group opens with the questions nearly everyone expects, and each question has a note on what to listen for and when to leave it alone.
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The questions
Each question, and why to ask it
Everyday
What is something most people do not know about you?
Why ask it
The person answering sets the depth, which is why this works as a first personal question: a hidden talent counts, and so does something much closer. Whatever size of answer you get is the right size. Pressing for 'something juicier' turns an invitation into a test.
What are you most passionate about?
Why ask it
Watch how fast they get going, because people tend to speed up and stop choosing their words when they reach the real answer. If it sounds like a line from an application form, ask what they would do all weekend if nobody were grading it. 'Nothing at the moment' may mean a flat stretch, so do not tease.
How would your closest friend describe you in three words?
Why ask it
Borrowing a friend's voice lets a modest person say good things and a guarded person say true ones. Ask which of the three words they would argue with. The gap between how they are seen and how they feel is the personal part.
What never fails to make you happy?
Why ask it
Hope for small, repeatable answers: a certain person's laugh, the first swim of the summer, a clean kitchen. They tell you what a good ordinary week looks like for this person. If they have to think for a long time, ask what used to do it.
What do you do when you have a whole day to yourself?
Why ask it
A free day shows what someone chooses when nobody is choosing for them. It is personal without being private, which makes it safe to ask almost anyone. If the answer is 'sleep', ask what they would do with the second free day.
What is your biggest pet peeve?
Why ask it
A complaint is the easiest personal thing to share, and the heat in it points at what they care about: someone maddened by lateness values their time, someone maddened by loud chewing needs quiet. If you are guilty of the thing they name, own up at once and laugh.
What is your lock screen, and why that picture?
Why ask it
They picked that picture to look at many times a day, so there is usually a reason. Let them show you if they want to, and do not reach for the phone yourself. If it is the default wallpaper, laugh and ask what they would put there.
Which of your habits would a new roommate notice first?
Why ask it
It gets you a real quirk because it asks what is visible, not what is wrong with them. Trade one of your own straight away, so it feels like comparing notes and not an inspection.
How do you usually spend the last hour before you go to sleep?
Why ask it
The end of the day is when a lot of people stop performing, so you hear about the scrolling, the reading or the lying awake. If lying awake comes up, 'what about?' is a much more personal follow-up, so ask it gently or leave it for later.
What are you like when you are tired or hungry?
Why ask it
Most people know this about themselves and usually enjoy confessing it. Remember the answer, because it tells you when not to bring up anything serious with them.
Who do you text the most, and what is it mostly about?
Why ask it
This tells you who their main person is without asking who matters most to them. If they hesitate, they may not want to name anyone, so add 'you can just say what it is about' and let the name go.
What is your most-played song this month, and what does it say about your mood?
Why ask it
Recent listening is a mood diary that people are happy to show. A month of sad songs or angry ones is an opening, and you can use it lightly: 'rough month, or just a good album?' Then let them pick which it is.
Are you the same person online as you are in person?
Why ask it
'Mostly' is the common answer, and the gap is the interesting part: bolder, funnier, quieter, more polished. With a teenager, do not turn the answer into a talk about screen time, or you will not get an honest one again.
What kind of compliment do you never quite know how to take?
Why ask it
The compliment someone squirms at tends to sit on something they are unsure about. Do not test it by paying them that compliment on the spot. Ask what kind they do like hearing.
What is your comfort show, song or food after a rough day?
Why ask it
It is a small look at how they take care of themselves, and it is useful later when they are having one of those days. 'Rough day' may bring a recent one to mind. If it does, ask whether they want to talk about it or just have the snack.
What do you spend more time on than you would like to admit?
Why ask it
'Admit' tells them a slightly embarrassing answer is welcome. Whatever it is, a game, a show, their hair, be interested and not amused. Mocking the first small confession closes the door on bigger ones.
How much time alone do you need before you start getting short with people?
Why ask it
It treats needing space as normal, which lets quieter people answer truthfully. The answer is practical too: a canceled plan from them may be about energy and not about you.
When you walk into a room full of strangers, what do you do first?
Why ask it
Find the food, find the one person they know, check the phone, start talking: each is a different way of handling nerves. If they say they hate those rooms, ask what makes one bearable, not why they are shy.
What do you wear when you want to feel most like yourself?
Why ask it
Clothes are a personal subject that is easy to talk about, and the answer tells you who they think they are. Keep your follow-ups on the feeling. Comments on their body or on what things cost are where this goes wrong.
What is the nickname that only certain people are allowed to use?
Why ask it
A restricted nickname marks out an inner circle, so you learn who is in it and how they got there. Do not start using the name yourself unless you are invited to.
What do you do first when you are in a bad mood?
Why ask it
Some people go quiet, some clean something, some pick a fight. Knowing their first move means you can spot the mood later without asking. Follow with 'and what do you want other people to do when you are like that?'
How do you like your birthday to go: a crowd, a few people, or as quietly as possible?
Why ask it
Birthdays show how someone feels about being the center of attention. Anyone who says they would rather skip theirs usually has a reason. Take the answer as it is, and do not ask why unless they offer.
What would you never post, even though it is a big part of your life?
Why ask it
This is the most personal question in the group, because it points at what they keep back on purpose: family, faith, a relationship, a struggle. They can name the category without the detail, and that is enough for now.
Growing up
What is your favorite memory from when you were a kid?
Why ask it
Ask who else is in the memory, because a favorite is usually about a person as much as an event: a grandfather's garden, a cousin's bunk bed. Some people have to search for a happy one. Give them time, and take a small answer like a snow day as a full one.
What did you want to be when you grew up?
Why ask it
The job matters less than what the small version of them thought it would feel like to be a vet or a pop star. Ask what happened to the plan. Some people are still quietly heading for it and some gave it up for a reason that stings, and the tone of the answer tells you which.
What was dinner like in your house: everyone at the table, or everyone on their own?
Why ask it
A meal is an easy way into family life, since it shows who was home, who talked and who was missing. If the answer is short or flat, leave the family alone for now and ask what they liked to eat.
Who were you closest to in your family growing up, and are you still?
Why ask it
It might be a parent, a grandmother, a cousin or the dog, and the second half tells you whether that closeness lasted, faded or ended with a death. Notice who is not mentioned, and keep that observation to yourself. 'Nobody, really' is an answer to be sorry about, not one to question.
What did a normal weekend look like in your family when you were small?
Why ask it
Weekends show what a family did when nothing was required: church, sports, chores, relatives, everyone in separate rooms. For someone who split weekends between two homes this is a bigger question, so let them choose which house to describe.
What smell puts you straight back in the house you grew up in?
Why ask it
A smell brings a whole room back, usually with people in it. Most answers are warm. If theirs is cigarette smoke or damp, they are telling you something real, so listen without making a face.
Were you a rule-follower as a kid, or the one testing every limit?
Why ask it
Either answer comes with stories, and most people enjoy telling them. Ask whether they are still that way. Someone who was the 'good' child often has more to say about what it cost than the rebel does.
What did you get praised for most as a kid?
Why ask it
What a child is praised for often becomes what the adult thinks they are for: being clever, being helpful, being no trouble. 'Do you still feel you have to be that?' is a good follow-up, but only if they already seem to be wondering.
Where did you go when you wanted to be alone as a kid?
Why ask it
The place is usually a nice memory: a tree, a closet, a bike ride with no destination. Why they needed it can be a heavier one, so ask about the place and let them decide whether to tell you the rest.
How did your family show affection: words, hugs, food, or doing things for each other?
Why ask it
It explains how they show care now, and what they may not recognize as care when it comes from you. Some people answer 'we didn't, really'. Take that calmly, say it sounds hard, and do not ask them to prove it.
Who has shaped the person you are more than anyone else?
Why ask it
The answer is not always someone they admire. People are shaped by the parent they copied and by the one they swore not to become, so ask 'in what way?' before you assume it is a tribute. If they name someone who has died, let them talk about that person for as long as they like.
Which adult outside your family made the biggest difference to you growing up?
Why ask it
It might be a coach, a neighbor or a friend's mother, and it is someone they are seldom asked about and glad to describe. If nobody comes to mind, ask who they wish had been around.
What were your parents strict about that your friends' parents were not?
Why ask it
The strict rule, whether it covered curfews, grades, phones or church, tells you what the household worried about. If they are a teenager still living under it, just listen. This is not the moment to argue the parents' case.
How did you get along with your brothers or sisters growing up, or what was it like being the only one?
Why ask it
Sibling history covers rivalry, protection and who got away with what, and the second half means an only child is not left out. If a sibling is mentioned in the past tense or skipped over, do not ask why. Wait to be told.
What did you do as a kid when you were upset: hide, shout, or go quiet?
Why ask it
Plenty of adults still do a grown-up version of the same thing, which makes this a gentle way to learn how they handle being hurt. Share what you did too, so nobody feels examined.
What did your family argue about most when you were growing up?
Why ask it
Money, chores, one person's temper, or nothing at all because nobody argued out loud. This is the point in the group where answers can turn serious. If theirs does, stop collecting details and say you are glad they told you.
What were you afraid of as a child that you never told anyone?
Why ask it
Childhood fears are far enough away to be told with a smile: the dark, the drain, a parent not coming back. That last kind is not a funny story. If you get one, do not laugh along out of habit.
What did you keep from your parents as a kid that seems harmless now?
Why ask it
'Harmless now' keeps it to the comic end: the hidden report card, the secret pet, the candy under the bed. With someone still living at home, make it clear you are not going to pass anything on.
What did you pretend to like so that you would fit in?
Why ask it
Almost everyone has an answer: a band, a sport, a drink, a group of friends. It opens up how much fitting in mattered to them and what they hid to manage it. With a teenager it may be happening now, so ask without teasing.
What was the hardest year of school for you, and what made it hard?
Why ask it
People can usually name the year at once. The reason might be a teacher, a move, a friend group that turned, or something at home. If they name the year and stop, that is the answer. Thank them and move on.
What childhood friendship ended, and do you know why?
Why ask it
Early friendships often end without an explanation, and many people still wonder about one. It is a soft way to talk about being left or leaving. Do not suggest they get in touch unless they bring it up.
What from your childhood would you pass on, and what would you leave behind?
Why ask it
It lets someone be fair to their upbringing: grateful for part of it and done with another part. The 'leave behind' half can be heavy. If they answer only the first half, they have told you how far they want to go.
What did you want from your parents that you did not know how to ask for?
Why ask it
This is the closest question in the group, so save it for someone who has already talked freely about home. Attention, praise, being left alone, an apology: whatever they say, do not defend the parents and do not attack them.
Feelings
What is your biggest dream for your life?
Why ask it
Ask it as if the dream were possible, since many people have learned to add 'but that's unrealistic' before anyone else can. Find out what the first small step would be, and do not start planning it for them. If it is a dream they have let go of, ask what they loved about it.
What are you most proud of so far?
Why ask it
The proudest thing is often not the one with a certificate. It may be leaving something, sticking at something, or looking after someone when it was hard. Ask what it cost them and who knows about it, because a proud thing nobody was told about is one they will be glad you asked for.
What do you like most about yourself?
Why ask it
A lot of people find this harder than naming a flaw, and some will dodge with something safe like 'my hair'. Let the safe answer stand, then ask what a friend would say. Do not answer for them, however sure you are. The point is hearing which quality they claim as their own.
What is your biggest fear?
Why ask it
You may get spiders, or you may get 'ending up like my dad', and the person answering decides which. Match the level they choose: joke about the spiders, go quiet for the other. Never use a fear someone has told you as a prank or a tease afterwards.
When someone asks how you are, how often is your answer the real one?
Why ask it
It lets a person admit that 'fine' is a habit without having to say how they are at this moment. If they answer 'not often', do not demand the real answer on the spot. Say you would like it whenever they feel like giving it.
What still makes you nervous every single time, however often you do it?
Why ask it
Phone calls, presentations, walking into a party, ordering food. A nerve that never goes away is easy to own up to because so many people share it. Offer yours too, and hold the tips unless they ask for them.
Where do you feel stress in your body first?
Why ask it
Stomach, shoulders, jaw, sleep. It is easier to answer than 'are you stressed?' because it asks for a fact instead of a confession. If they say they have felt it a lot lately, ask whether they want to say what is behind it.
What was the happiest stretch of your life so far, and did you know it at the time?
Why ask it
People often name a period that looked ordinary while it was happening. Ask what made it good: who was around, what they were free of. If the answer is 'I'm not sure I've had one yet', take it seriously and ask what they picture it looking like.
What are you most grateful for right now?
Why ask it
'Right now' brings out this month's answer instead of the dutiful one about health and family. It is a kind question for someone having a hard time, provided you do not use it to tell them to count their blessings. If the answer is a person, ask whether that person knows.
When did you last feel properly proud of yourself?
Why ask it
Many people find pride harder to talk about than embarrassment, so give them time. If nothing comes, do not hurry to supply reasons they should be proud. Ask what they would like to feel proud of.
Do you cry easily, rarely or never, and has that changed?
Why ask it
It asks about the pattern, not the last time, so nobody has to relive anything. Boys and men are often told early not to cry and may answer with a joke. Take the joke, and do not push past it.
What is the last thing you were embarrassed about for longer than it deserved?
Why ask it
A wrong name, a wave at someone who was waving at somebody else, a message sent to the wrong chat. Small embarrassments are fun to trade. If theirs clearly still hurts, do not laugh until they do.
What do you get homesick for?
Why ask it
It may be a place, a person, a time of life or an earlier version of themselves. The answer shows what has been lost or left behind, in a form that is easy to say. For someone who has moved far or lost a home this is tender, so go slowly.
What is a fear you have grown out of, and one you have grown into?
Why ask it
The first half is easy and often funny. The second is where the answer is: heights, driving, losing people, running out of time. The fears people grow into say a lot about what they now have to lose.
Where do you hope to be in five years?
Why ask it
'Hope' makes it a question about wishes, where 'see yourself' sounds like a job interview. Listen for what they mention first, whether a place, a person or a kind of work, since that is the part they are most attached to. With someone you are dating, do not treat the answer as a verdict on the two of you.
What kind of news do you keep to yourself for a while before telling anyone?
Why ask it
Some people sit on bad news, others on good news in case it falls through. If you are close to them, it also explains why you sometimes hear things late, and that the delay is not a judgment on you.
What do you compare yourself to other people on, even though you know better?
Why ask it
Looks, grades, money, how many friends they have, how far along they are. 'Even though you know better' gives them credit and makes it easier to admit. 'But you are great at that' ends the conversation and rarely convinces, so skip it.
What helps when you are anxious, and what do people do that makes it worse?
Why ask it
The second half is the valuable part: being told to calm down, too many questions, being watched. If you have done one of those things to them, say so and say you will stop. That is worth more than any follow-up question.
What are you harder on yourself about than you would ever be on a friend?
Why ask it
Putting a friend in the question lets them see the double standard for themselves. Do not point it out or argue with their answer. 'What would you say to a friend who felt that?' is as far as you need to go.
What would you change about yourself if you could?
Why ask it
Ask this only if you can hear the answer without correcting it. Appearance comes up a lot, and with a girl or a guy you like, 'I think you look great' can sound as if you were not listening. Ask how long they have wanted that, and whether it is their own wish or somebody else's comment.
What does it take for you to ask for help?
Why ask it
For some people the answer is 'a crisis', which tells you how bad things get before they speak up. Ask what would make it easier, and offer a low-effort signal, such as a single word by text that means 'call me'.
How do you know you are not okay, before anyone else can tell?
Why ask it
They are describing their own early warning signs: sleeping more, replying less, snapping, a messy room. Ask whether they would like you to say something when you see them. Some people will say yes and some will say please don't.
What worry have you had for so long that it feels normal?
Why ask it
This reaches the background worries: money, a parent's health, not being good enough. Do not try to solve it in one conversation. If the worry sounds like it is running their life, it is fair to ask whether they have someone to talk to about it.
What unkind thing did someone say to you that you have never quite shaken?
Why ask it
Many people carry one sentence from a parent, a teacher, a classmate or an ex, and hearing it tells you where to be careful with them. Do not rush to say it is not true. Ask how old they were, and let them be the one to say how wrong it was.
When did you last feel really understood, and by whom?
Why ask it
It ends the group on something good and tells you what being understood looks like to them: advice, silence, or someone simply getting the joke. If they cannot think of a time, that is a sad answer. Stay with it for a moment before you move on.
Relationships
What do you value most in a friend?
Why ask it
Whichever quality they name first, whether loyalty, honesty or just showing up, treat it as instructions if you are the friend. Ask for a time someone got it exactly right. That is a happier story than who got it wrong, and it tells you the same thing.
What was your first impression of me?
Why ask it
Only ask if you can laugh at 'I thought you were stuck up'. With a boyfriend, girlfriend or good friend the fun is in how wrong the first guess was, so ask when it changed. Offer your first impression of them too, and make it both kind and true.
What is your favorite memory of the two of us?
Why ask it
Friends and couples often pick different moments, and hearing theirs shows what they treasure about being around you. It may be a day you had forgotten. Do not correct the details. Say yours afterwards, and plan something like it again.
What makes you feel close to someone: time together, talking, or going through something hard?
Why ask it
People build closeness in different ways, and mismatches cause a lot of hurt that nobody intended. If their way is talking and yours is doing things side by side, say so now. It is useful to both of you.
How do you show someone you care when you are not saying it out loud?
Why ask it
Once you know their method, whether it is sending a song, fixing something or teasing, you will start to notice it. It is a kind thing to ask a boyfriend, girlfriend or friend who finds the words difficult.
What are you like when you have a crush: obvious, or impossible to read?
Why ask it
It is playful and still personal, and it suits friends at a sleepover as well as someone you are getting to know. If you are asking the person you like, be ready to have it asked back. Do not use it to dig for a name.
What did your first crush teach you about yourself?
Why ask it
A first crush is far enough back to be funny, and asking what it taught them turns gossip into something to think about. If they would rather not name names, the lesson alone is plenty.
Have you ever been in love, and how did you know?
Why ask it
The second half is the personal part, because it asks what love feels like from the inside for this person: calm, panic, or wanting to tell them everything first. With someone you are dating, ask about the feeling and not about the ex. 'I'm not sure I have' is a perfectly good answer at any age.
Do you fall for people fast, or does it creep up on you?
Why ask it
This tells you about pace, which matters a great deal if you are the one they might be falling for. Neither answer is better. If you are dating, share your own pace honestly, even when it differs from theirs.
What do you look for in a partner?
Why ask it
First answers tend to be a stock list: funny, kind, ambitious. Ask which quality they came to care about through experience, and you get a real one. If you are dating them, do not check yourself against the list out loud, which turns their answer into an audition.
What is a deal-breaker for you in a relationship?
Why ask it
A deal-breaker is a boundary stated in advance, and it is kinder to hear it early than to find it out. It may be lying, smoking, or not wanting children. Do not argue with theirs or try to bargain it down, and if it describes you, say so soon.
What small thing can someone do that makes you feel loved?
Why ask it
'Small' keeps the answers practical: a text when they get home, the last bite, being walked to the door. If you are their partner or close friend, do the thing within the week. It shows you were listening better than anything you could say.
When you are upset with someone, do you tell them or wait for it to pass?
Why ask it
Either way, you now know what their silence might mean. If they say they wait, ask how you would be able to tell. Ask out of curiosity and not about a particular incident, or it becomes the argument.
How do you say sorry: quickly, slowly, or with a gesture instead of words?
Why ask it
Some people apologize with a cup of tea and never say the word. If you know that in advance, you will not miss the apology when it comes. Ask what kind they need to receive as well, because it is often a different kind.
How would you want to be told that you had hurt someone's feelings?
Why ask it
Right away or later, in person or in writing, bluntly or gently. You are getting the instructions before you need them. It is a good one for couples and close friends to answer in both directions.
What do you get jealous about in a friendship or a relationship?
Why ask it
Jealousy is embarrassing to admit, whether it is over a partner's ex, a friend's new friend or being left out of plans, so thank them for the honesty. Do not use the answer to tease them or to test them later.
What would someone have to do to lose your trust for good?
Why ask it
The rule they give, such as no lying or no repeating secrets, usually comes from something that happened. Whether to tell that story is up to them, so if they stop at the rule, stop there with them.
What do you and your closest friend never talk about?
Why ask it
Most close friendships have a subject they steer around, and naming it says a lot about both people. You are asking what the subject is, not for the details. If they say they would rather not get into it, smile and move on.
Are you comfortable by yourself, or do you feel better when you are with someone?
Why ask it
It applies to being single and to being alone on a Saturday. Listen for whether time alone is a choice or something they put up with. Never follow it with 'so why are you single?', which turns a question into a verdict.
When did you last tell someone you loved them, and was it easy to say?
Why ask it
In some families and friendships it is said daily, and in others never. The second half matters more than the first. If the words are hard for them, do not read their silence as a lack of feeling.
Who in your family do you find it hardest to talk to?
Why ask it
Many people have one, and the reason may be mild, such as nothing in common, or serious. Ask what they wish they could talk about with that person. If the mood drops, do not ask why it is hard.
Is there someone you miss that you could still call?
Why ask it
This covers a friend who drifted, a relative, or an ex they think about. It only asks whether the person exists, so they are free to stop at yes. Whether to get in touch is their decision, so do not push them toward the phone.
What do you do differently now because of a friendship or relationship that ended?
Why ask it
It asks for the lesson and not the story, so nobody has to explain who did what. Listen for whether the change was toward being more open or more guarded. With a new partner, do not ask who it was about.
Have you ever had your heart broken, and how long did it take to feel normal again?
Why ask it
Asking how long it took makes it a question about getting better, so they can answer without going back over what happened. If the answer is 'I'm not sure I have', it is recent or still raw. Say you are sorry and ask nothing more about the other person.
Do you want to get married or have kids someday, or is that still an open question?
Why ask it
Offering 'open question' matters, because many people do not know and some cannot have what they want. With a boyfriend or girlfriend, ask out of curiosity and not as a negotiation, and not in the first few weeks. 'I don't know' is a full answer.
Beliefs
What is the best advice anyone has ever given you?
Why ask it
Who gave the advice matters as much as what it was, so ask about the person and the day it was said. You are also learning a rule they live by. If they cannot think of any, ask for the worst advice they ever got, which is often quicker to recall.
What matters most to you in life right now?
Why ask it
'Right now' is in the question because the answer moves: it might be exams one year and a person the next. Ask whether it would have been the same two years ago. Their order of priorities is theirs, so do not hold it up against your own.
What are you superstitious about, even a little?
Why ask it
Lucky socks, knocking on wood, not saying a good thing out loud in case it gets jinxed. It is the lightest way into what someone believes about luck and control. Enjoy the answer and do not argue with it.
Do you believe in ghosts, signs or anything else you cannot explain?
Why ask it
Plenty of people have one story they half believe. For some, a 'sign' is tied to a person who has died. If their voice changes, treat it as a story about that person and not as a debate about ghosts.
Do you think things happen for a reason, or do we add the reason afterward?
Why ask it
The answer shapes how a person deals with bad luck, so be careful if they have had a recent loss. 'Everything happens for a reason' comforts one person and hurts another. Ask what they think, and keep your own verdict out of it.
Were you raised with a religion, and what have you kept from it?
Why ask it
Asking what they kept lets a believer, a doubter and someone who walked away all answer without defending themselves. Stay curious about their experience. Once you start arguing about whether it is true, it is no longer a personal question.
Do you pray, meditate, or have your own version of talking to the universe?
Why ask it
Plenty of people who would not call themselves religious still do something like this in a hospital corridor or before an exam. It is private, so a short answer is fine. Ask what it does for them, not who they think is listening.
Where does your sense of right and wrong come from: family, faith, experience, your own gut?
Why ask it
Few people get asked this, so expect them to work it out as they answer. Ask for a time their own sense disagreed with what they were taught. That story tells you more than the general answer.
What do you believe that your family does not?
Why ask it
It could be politics, religion, how to raise children or what counts as a proper job. It shows where they have had to stand apart. If they still live at home this may be a daily strain, so keep what they tell you to yourself.
Do you think people can really change?
Why ask it
The answer is often about a specific person: a parent, an ex, themselves. You can ask 'who are you thinking of?' once. If they wave it away, stay with the general question.
Do you believe in soulmates, or in choosing someone and working at it?
Why ask it
It sounds like a movie question and tells you how they think love works, which is useful if you are dating them. People who disagree on this can still do well together. What matters is that each of you knows what the other expects.
Do you think most people are basically good?
Why ask it
A fast yes or a fast no usually has experience behind it. Ask what makes them say so, and be ready for an account of being helped by a stranger or badly let down by someone they knew.
Does everyone deserve a second chance, or are some things unforgivable?
Why ask it
Start with it as a matter of principle. People who have been badly wronged often answer from that, and they may not want to say what it was. If they name something as unforgivable, do not ask them to justify it.
Do you think boys and girls are taught to handle feelings differently, and did that happen to you?
Why ask it
The second half makes it personal: who was told to toughen up, and who was told to smile and keep the peace. It is a good one to ask a guy or a girl you are getting to know, as long as you want their experience and not a debate.
What issue do you care about because of something that happened to you or to someone close to you?
Why ask it
It skips the argument and goes to the reason, and people are far easier to understand that way. You do not have to agree with the view to respect where it came from. If the story involves illness, money trouble or someone being mistreated, listen and leave the politics alone.
Is there anything you would risk a friendship to stand up for?
Why ask it
This finds the line where a belief becomes more important than being liked. Some people have already paid that price and will tell you about the friend they lost. Ask whether they would do it again.
Is it ever right to keep a secret from someone you love?
Why ask it
Surprise parties are easy, and then it gets harder: a diagnosis, a debt, something from the past. Between partners, keep it hypothetical. If it starts to sound like an interrogation about a real secret, say plainly that it is not one.
How do you decide when your head and your gut disagree?
Why ask it
Ask for the last time it happened and which one they followed. You learn how they make big decisions and whether they trust themselves, which is more personal than it first sounds.
What does home mean to you: a place, certain people, or a feeling?
Why ask it
For someone who moved a lot, lost a home, or never felt at ease in theirs, this is a deep question dressed as a simple one. If they answer with a person, ask about that person. If they are not sure they have a home, do not rush to fix it.
What do you think happens after we die?
Why ask it
Nobody needs to be certain here, including you. Do not ask it of someone recently bereaved or seriously ill unless they raise it first. If your views differ, say 'I see it differently' and leave it there.
What do you hold on to when things go badly?
Why ask it
A faith, a saying from a grandparent, the thought that it will pass, one particular friend. It is the belief they actually use, as opposed to the ones they would list. It also leads into the last group, if they want to say when they last needed it.
Only if ready
How are you really doing at the moment?
Why ask it
The word 'really' only works if you have time to hear the answer and somewhere private to hear it. Ask once, then wait. If they say 'fine' again, accept it and say the offer stays open. Asking a second time puts pressure on them.
What are you going through right now that you have not told many people?
Why ask it
Ask this only when they have already hinted that something is going on, and promise to keep it to yourself only if you can. If what they tell you means they or someone else is in danger, say kindly that you will need to bring in someone who can help.
What is the hardest thing you have been through, and who or what got you through it?
Why ask it
The second half gives them something steadier to talk about than the event. They may name the event in five words and spend ten minutes on the person who helped, and that is a complete answer. Do not ask for the parts they left out.
Is there something about your family that you do not usually tell people?
Why ask it
'Is there something' lets them say yes and stop, which matters when the something is illness, addiction, money or a parent who left. If they tell you, do not look shocked, and do not repeat it to anyone, including people who know the family.
Did your parents stay together, and how was that for you either way?
Why ask it
'Either way' is there because a marriage that lasted can be as hard on a child as one that ended. Do not say you are sorry before you know how they feel about it. Some people were relieved.
Has money ever been a real worry in your family?
Why ask it
Shame about money is rarely spoken, so ask this only of someone who trusts you and never in front of others. A yes may explain a lot about how they spend, save or refuse help. Do not start offering to pay for things right afterward.
Have you lost someone close to you, and what do you miss most about them?
Why ask it
Many grieving people want to talk about the person and find that the people around them avoid the subject. Asking what they miss brings the person into the conversation, not the death. If they tear up, you have done nothing wrong. Stay, and let them go on or stop.
Were you ever bullied, or did you ever bully someone?
Why ask it
Asking both halves is honest, because plenty of people did some of each. With a teenager it may be happening now. If it is, hear all of it, and ask what they would like to happen before you do anything.
Who let you down when you needed them most?
Why ask it
It asks them to name someone, which is hard, so wait until they have already brought up a difficult time. Do not join in attacking the person, who may be a parent they still love. 'That should not have happened to you' is enough.
What is your biggest insecurity?
Why ask it
This only belongs between people who already trust each other, and never in front of a group. The answer is a map of where a careless joke would land hardest, so treat it that way from now on. A good next question is when it bothers them most, since that is often a setting you can help with.
How do you feel about the way you look, on an honest day?
Why ask it
Never ask this as a way into giving your own opinion, good or bad. If they tell you what they dislike, do not contradict them and do not agree. Thank them for telling you, and ask how long they have felt that way.
What do you deal with, in your body or your mind, that people cannot see?
Why ask it
It could be pain, a diagnosis, panic or low moods, and whether to tell is up to them. If they do, ask what helps and what they would like you to do on a bad day. Do not suggest cures.
Have you ever talked to a counselor or therapist, and did it help?
Why ask it
Asked without any weight, it treats getting help as ordinary. Ask whether it helped, not what it was for. If they have wanted to and have not, ask what is in the way. For a teenager a school counselor or a doctor can be a first step.
When have you felt most alone?
Why ask it
The answer is often a time when they were surrounded by people: a new school, a bad relationship, a house full of family. Do not answer with a lonelier story of your own. If they say 'now', stop asking questions and make a plan to see them soon.
What are you still angry about?
Why ask it
Anger that has lasted is usually about something unfair that was never put right. Let them be angry, and do not hurry them toward forgiving anyone. If the anger is at you, hear it through to the end before you answer.
What do you regret that you have never really talked about?
Why ask it
They may tell you the regret, or only that there is one. Either is fine. Do not say it was not their fault unless you know the whole story. Ask what they would want to say to the person involved.
Is there a memory you would rather not have?
Why ask it
This is a yes or no question, and it should stay one unless they choose to say more. Never ask what the memory is. If they tell you about something that harmed them, believe them, thank them for trusting you, and ask whether they have support.
What scares you most about the future?
Why ask it
Failing, ending up alone, a parent getting old, the state of the world, turning into someone they do not like. Do not reassure them too fast. Ask what would make it a little less frightening, which may be something small you can help with.
What do you wish someone had noticed about you when you were younger?
Why ask it
It lets them describe an old hurt as a wish, which is easier to say: that they were struggling, that they were good at something, that they were not fine. You cannot go back and notice it, but you can say that you see it now.
What would you want me to know about you that is hard to say?
Why ask it
Keep this for the end of a long, honest conversation with someone you intend to stay close to. Let the silence run. If nothing comes, say 'whenever you want to' and mean it. If something does, thank them and hold the advice.
How to ask a personal question without prying
Practical guidance for the conversation itself
Choosing how personal to go
Work down the groups in order
The six groups run from mild to close. Everyday and the first half of Growing up are fine with someone you have known for a week. Feelings and Relationships need some trust in both directions. Beliefs can be asked of almost anyone, provided you are asking and not arguing. Only if ready is for people who already confide in you. Inside a group, the familiar questions come first (what someone is passionate about, proud of or afraid of) and the closest ones sit near the end.
Tell before you ask
A personal question is easier to answer after the asker has gone first. Before you ask what someone was afraid of as a child, say what you were afraid of. Keep your version short and about the same size as the answer you are hoping for. If you would not answer the question yourself, do not ask it.
Pick the place
Ask one to one, with nobody listening and enough time to hear the answer. Side by side is easier than face to face: walking, driving, washing dishes, sitting on a step. A personal question asked in front of a group is a performance, and the person answering knows it.
Ask if you can ask
For anything in the last two groups, start with 'Can I ask you something personal? You can say no.' It costs five seconds and it hands them the decision. If they say 'not right now', say 'of course' and change the subject yourself, so they do not have to.
A girl, a guy, a partner or your friends
A girl or a guy you like
The questions do not change with who you are asking. What changes is how well you know them. Early on, stay in Everyday and the lighter Growing up questions: something most people do not know about them, the lock screen, what they wanted to be as a kid. The crush questions in Relationships are playful once you are both relaxed, and by then what they look for in a partner is fair to ask too. Leave heartbreak, marriage and anything in Only if ready until they have started telling you things unprompted.
Your boyfriend or girlfriend
Start with the two about the pair of you, your first impressions and a favorite memory, which are easy to enjoy. The middle of the Relationships group is written for the harder part: how each of you says sorry, what makes you jealous, how you want to be told you have hurt the other. Ask one at a calm moment, never in the middle of an argument, and answer it yourself as well. The answer is something to remember, and it should never be brought out as evidence in the next disagreement.
Your friends
With a group, keep to Everyday, the lighter half of Growing up, the embarrassment and nerves questions in Feelings, and the crush questions. Go around, let anyone pass without comment, and agree that what is said stays in the room. The closer questions belong to one friend at a time, usually late, usually when they have brought something up first.
Over text
Some people find hard things easier to type than to say, because nobody is watching their face. Send one question with your own answer attached, and do not chase a slow reply. Never screenshot or forward what comes back. The last group is better kept for when you are together, unless they are the one who starts it.
When a question is too much
Signs you have gone too far
The answers get shorter. A joke arrives where an answer should be. They look away, change the subject, or turn the question back on you at once. Someone who was talking freely says 'I don't know'. Any one of these means stop. You do not need to work out why.
How to back off
- 1Say 'you don't have to answer that' as soon as you see them hesitate.
- 2Keep the apology to one sentence. A long one makes them look after you.
- 3Answer the question yourself, or move to something from Everyday.
- 4Do not come back to it later the same day. If they want to answer, they will bring it up.
When they tell you something heavy
Say 'thank you for telling me' before anything else. Ask whether they want you to listen or to help, and believe the answer. Do not reply with a bigger story of your own, do not offer a fix they did not ask for, and do not go quiet out of shock. 'That sounds really hard' is a full reply.
What stays between you, and what cannot
What you are told in an answer is not yours to pass on, including to people who would be kind about it. The exception is safety. If someone says they are being hurt, or talks about hurting themselves, tell them you care too much to keep that one secret, and help them reach a parent, a teacher, a school counselor, a doctor or a local crisis line.
Personal is not the same as prying
Questions that are nobody's business
Nothing on this page asks about someone's body, weight, sex life, exact income or medical history, or for a secret that belongs to a third person. Those are prying however kindly they are put. A personal question asks about someone's experience and leaves them in charge of how much to show.
Asking to confirm a suspicion
If you already think you know the answer and want to catch them out, you are making an accusation with a question mark on it. Say what you are worried about instead: 'you have seemed low lately and I wanted to check in.'
Too many in a row
Two or three personal questions are plenty for one conversation. More than that and the other person starts to feel studied. Stay with one answer, ask what happened next, and let them ask you something before you go on.
Using an answer later
The fastest way to make sure someone never tells you anything again is to repeat their answer as a joke in front of others or throw it back in an argument. What you learn here is for understanding them better, and for nothing else.