Questions to Ask to Get to Know Someone
Good questions to ask people you want to know better: someone you just met, a date, a new friend, a colleague, a relative you have never really talked to. There are 137 here, running from light openers through tastes, daily life and background to the people in their life and a last group of deeper ones. They are questions to ask someone to get to know them one to one, not prompts for going around a group.
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The questions
Each question, and why to ask it
Openers
What do you like to do in your free time?
Why ask it
The plainest question on the list, and one that nearly everyone can answer on the spot. Take whatever they name seriously, whether it is climbing or reorganizing the garage, and ask how they got into it. There is usually a person, a place or a present behind it. If they say they have no free time, ask what they would do with one spare Saturday.
Where did you grow up, and what was it like there?
Why ask it
The second half is what makes it worth asking. A town name on its own gets a nod. 'What was it like' gets the street, the weather and whether they could not wait to leave. If they moved a lot, or the subject seems sore, take the short answer and ask where feels like home now.
What do you do for a living, and what do you like about it?
Why ask it
Strangers ask each other the first half all day long, and the second half is what rescues it. A job title tells you little. The part of the work they enjoy tells you what they are good at and what they would look for in the next job. Not everyone has a job to describe, so listen to how they answer and be ready to ask what fills their days instead.
What are you looking forward to in the next month or so?
Why ask it
Plans already on the calendar are easier to talk about than hopes. A trip, a visit or a concert gives you something to ask about the next time you meet. If nothing comes to mind, ask what they would put on the calendar if they could.
What does a perfect day off look like for you?
Why ask it
People describe either a day full of plans or a day with none at all, and it helps to know which kind of person you are talking to. Listen for who else is in it and what time it starts. Then ask what their last day off was really like. The gap between the two is often funny, and sometimes it is the thing they would most like to fix.
What have you been up to lately, outside of work?
Why ask it
Close to what people ask each other anyway, so it never sounds prepared. 'Outside of work' moves them off the job title and onto whatever fills their evenings. Swap in school or the kids if that is what their days are made of.
What do you do when you need to switch off?
Why ask it
Running, baking and three hours of television are all good answers, and each one suggests something you could do together later. If they say they never manage to switch off, ask what gets in the way before you offer any advice.
What do you usually end up talking about with your friends?
Why ask it
A back way to someone's interests that skips the word hobbies, which makes a lot of people go blank. If the answer is work, television and other friends, you have three places to go next.
What were you doing this time last year?
Why ask it
A year is close enough to remember and far enough to show movement. People notice halfway through the answer how much has changed, whether a job, an apartment or a person, and tell you which change mattered.
What has been the best part of your week so far?
Why ask it
A week is short enough to remember and long enough to hold one good thing. If nothing comes to mind, ask what would have made it better. That version often gets the more honest answer.
How do you know the host, or the friend we have in common?
Why ask it
The one thing two strangers at a gathering are sure to share is the person who invited them. How they met that person gives you a mutual subject, and it places them: school, work, the old neighborhood.
What did you do last weekend that you would happily do again?
Why ask it
Ask what someone did over the weekend and you get a list of errands. The filter picks out the one part they enjoyed, and if it sounds good to you as well, you have something to suggest doing together.
What have you eaten recently that you are still thinking about?
Why ask it
Recently keeps it honest: a bowl of noodles from last Thursday, not a famous restaurant from years ago. You find out whether they cook and where they eat, and you often leave with a recommendation.
Is there a story behind that ring, that bag or that sticker on your laptop?
Why ask it
Point it at whatever they have with them that looks chosen and not just bought. Things people carry every day usually have a giver or a trip attached, and they get to decide how much of it to tell.
How has today treated you, honestly?
Why ask it
The last word gives permission to say more than fine. If the day was bad, stay with it for a minute and then let it go. That alone is more attention than most small talk offers.
What is taking up most of your head space at the moment?
Why ask it
Catches them where they are today instead of in general. It can be a house move, an exam or a sick dog. If they wave it away with 'oh, the usual', take the hint and go back to something lighter.
What would you be doing right now if you were not here?
Why ask it
A playful way to hear what an ordinary evening looks like for them. It can sound as if you are offering an exit, so ask it with a smile, and go first with what you would be doing.
Are you more of a talker or a listener when you meet someone new?
Why ask it
It comments on the conversation you are in, which is why it helps. Whatever they say tells you how to pace the rest of it: leave longer gaps for a listener, and give a talker something they can run with.
What is a small win you have had lately?
Why ask it
Small is the important word. It lets someone mention the leaking tap fixed or the difficult email finally sent, which they would never offer as an achievement, and it sets a cheerful tone early.
Is there anything coming up that you are a little nervous about?
Why ask it
The other side of asking what they are looking forward to. A driving test, a presentation or a first day somewhere gives you a date to remember, and a message afterward asking how it went is the kind of thing that turns an acquaintance into a friend.
Is there anything you are trying to do less of?
Why ask it
The mirror image of asking about goals, and easier to answer truthfully. Scrolling, saying yes to everything and late nights are common answers. Admit to one of yours so it does not sound like an inspection.
Tastes
What could you talk about for hours?
Why ask it
The surest way to watch someone come alive. It might be a football team, sourdough, a period of history or their dog, and the subject matters less than the change in their voice. Ask one real question about it and let them run. You do not have to share the interest to enjoy the enthusiasm.
What kind of music do you listen to, and what is on repeat right now?
Why ask it
The first half gets a genre, which says little. The second gets one song or album, and people will often play you a few seconds of it there and then. Ask where they first heard it. If they say they listen to a bit of everything, ask what was playing in the house when they were growing up.
What is your favorite film, the one you have seen more times than you can count?
Why ask it
Counting the rewatches keeps it honest. People name the film they love, not the one they feel they ought to admire, and it is often tied to an age or to whoever they first saw it with. If you have not seen it, ask what you would need to know going in.
What is your favorite thing to eat, the meal you would ask for on your birthday?
Why ask it
A birthday dinner is the honest favorite. It is rarely the most impressive dish and often something a parent or grandparent used to make. Ask who cooks it best and whether they can make it themselves. Then file the answer away: knowing someone's favorite meal is the kind of small fact that makes a later invitation feel thought about.
What never fails to make you laugh?
Why ask it
One particular friend, a scene in an old sitcom, their own dog falling off the sofa. A sense of humor is hard to describe and easy to show, so expect an impression or a clip on their phone. Dry, silly or dark, what they find funny tells you which kind of joke is safe to make with them.
What is the best thing you have read or watched this year?
Why ask it
What someone finished this year says more than a favorite film of all time, which tends to be a decade out of date. Write the title down in front of them, and if you do get to it, tell them what you thought. Very few people ever do.
What do you get competitive about?
Why ask it
Board games, parking, quiz nights, who gets to the airport earliest. Plenty of people say they are not competitive and then name the one arena where they are, laughing as they do. Good to know before you suggest a friendly game of anything.
Which album or artist takes you straight back to a particular year?
Why ask it
Music tends to get filed by date. You hear about the song and then the year, the bedroom, the car and who else was in it, which is far more than a list of favorite bands would give you.
Is there a book, film or song you think you met at exactly the right age?
Why ask it
Timing is half of taste. People name the thing and then the age, and the age opens up what was happening in their life when it landed. Ask whether it still holds up.
Do you play anything: a sport, an instrument, cards?
Why ask it
Three kinds of answer in one question, so the person who gave up the piano at twelve still has something to say. Ask who they play with. A weekly pickup game or a card night is a whole circle of friends you have not heard about yet.
Do you have a hidden talent, or a party trick?
Why ask it
Juggling, flawless parallel parking, every capital city in order, a whistle that stops traffic. The skill is usually useless and was learned at about eleven, which is the charm of it. Do not insist on a demonstration. If they want to show you, they will.
What have you always wanted to learn?
Why ask it
A language, the piano, how to swim properly, how to fix a car. The follow-up is what has stopped them, and the answer is mostly time, money or not wanting to be a beginner in front of other people. If it is something you know how to do, offer once and leave it there.
What kind of film, book or show can you not get enough of, even the bad ones?
Why ask it
The last four words are the point. Anyone can name a good film, but a person who will watch any heist, any courtroom or any baking final has told you what they find satisfying.
Whose work do you follow closely: a writer, a musician, a chef, an athlete?
Why ask it
Following one person's work for years is different from liking a genre. Ask what they came across first, and which piece they would hand to a beginner. Fans have strong views on where to start.
What will you not eat, and since when?
Why ask it
Dislikes are more specific than likes and often come with a childhood dinner table or one bad night attached. It is also practical, if you are ever going to cook for them. If the reason is medical or religious, take it as given and do not ask them to justify it.
What did you dislike for years and now love?
Why ask it
Olives, running, opera, the town they grew up in. A conversion comes with a before, an after and often a person who talked them into it. Ask who that was.
What is your biggest pet peeve?
Why ask it
Loud chewing, slow walkers, people who reply to everyone on an email. Small irritations are safe to complain about and funny to compare, and you find out what not to do around them. If the list gets long and bitter, steer back to something they like.
What is your idea of a treat?
Why ask it
A treat is whatever someone allows themselves only now and then, so the answer shows both what they love and what they ration. A good coffee and a whole afternoon with the phone off describe two different lives.
What have you bought in the last few years that earned its keep?
Why ask it
People answer with a mattress, a bicycle or a decent knife, and then explain what it fixed. You learn what they do every day and what they think money is for.
If you could travel anywhere at all next year, where would you go?
Why ask it
Giving it a year turns a daydream into a choice, so they have to pick one place from a long list. Ask what they picture doing there. Someone who wants the food markets and someone who wants an empty beach have given different answers even when they name the same country. If they have no wish to go anywhere, ask what they like about staying put.
Where have you been that you would go back to tomorrow?
Why ask it
Going back is a stricter test than having liked it. The places people would return to are usually about a feeling or a person as much as the sights, so ask what they would do on the first morning.
What kind of trip do you come back from rested?
Why ask it
Separates the trips people take from the ones that suit them. Someone who needs a week of nothing and someone who needs an itinerary can still travel together, but it helps to know before you book.
What is at the top of your bucket list?
Why ask it
It may be a trip, a marathon, seeing one particular band or learning to sail. Ask how long it has been up there and what would have to happen for them to do it. Some people dislike the whole idea of a list like this, and what they would sooner do with their time is just as good an answer.
What do you like doing alone that most people do in company?
Why ask it
Movies, restaurants, concerts, whole vacations. People who do these alone are often quietly proud of it, so ask about the first time they tried. If the answer is nothing at all, you have learned that they would rather have company for most things.
Are you someone who has hobbies, or someone who has phases?
Why ask it
You can tell from the laugh which one they are. The phase people have a closet of abandoned equipment and are funny about it. The hobby people will tell you how many years it has been.
What are you loyal to for no good reason: a team, a brand, a diner?
Why ask it
Sticking with a team that never wins or a pen that is no longer made is harmless and says a lot. Ask when it started. There is usually a parent, a first apartment or a first paycheck behind it.
Daily life
Are you an early bird or a night owl?
Why ask it
Quick to answer and more useful than it looks. It tells you when to call, whether a breakfast plan is a kindness or a punishment, and which of you will be yawning at ten. Ask whether it is by nature or by necessity. Plenty of night owls are up at six because of work or children, and have opinions about it.
How did you end up doing what you do?
Why ask it
Asks for a path instead of a role. Most careers turned on an accident or a person who intervened, and that is the part worth hearing. A two-word answer tends to mean they are tired of the job, not of you.
What was your first job, and what did it teach you that the later ones did not?
Why ask it
First jobs are funny in hindsight, whether it was a paper route, a stockroom or a summer of washing dishes. The lesson is nearly always about people: a boss, the customers, or what it is like to be ignored.
What would you keep about your job if you could change everything else?
Why ask it
Kinder than asking whether they like their work. Even someone on the way out can name the colleague, the commute or the one task they would keep, and what they leave off the list tells you the rest.
What is the hardest part of what you do that nobody sees?
Why ask it
Every job has work that is invisible from outside, and people brighten when someone asks about it. It does not need a paid job: a parent at home, a student or a caregiver has an answer too.
Who taught you how to do your job properly?
Why ask it
Rarely the person whose job it was to train them. You hear about a mentor or one patient colleague, and it is worth asking whether they have since done the same for someone newer.
What do you mainly work for: the money, the people, the craft or the cause?
Why ask it
None of the four is a wrong answer, and most people have thought about it more than they let on. Whichever they pick is the thing that would make them leave a job if it went, and keep them there through a bad year if it stayed.
What would you do for work if money were no object?
Why ask it
The dream job question without the word dream. Answers split between a different job altogether and the present one with fewer hours, and the second kind tells you they mostly like what they do. Ask what is the closest thing to it that they have actually tried.
What does your week ask of you that does not come naturally?
Why ask it
A gentler way to ask about weaknesses. Shy people who present for a living and disorganized people who run schedules have usually built a workaround, and the workaround is the part to ask about.
What are you like to work with, according to the people who do?
Why ask it
People quote real feedback here, good and bad: organized, blunt, never reads to the end of the email. Listen for what they add in their own defense. With a new colleague the answer doubles as instructions for working with them.
What are you working on that you would be pleased to finish?
Why ask it
It can be a report, a shed or a degree. Remember what it was and ask how it is going the next time you meet. Being remembered is what makes someone glad to see you again.
What made you choose the place you live in now?
Why ask it
Homes get chosen for the rent, a partner, a school or a view, so the reason is a snapshot of what mattered to them that year. Ask what they would look for next time.
Do you have any pets, or did you grow up with one?
Why ask it
People with animals will talk about them for as long as you let them, and there are usually photographs. The second half is for everyone else: a childhood dog or a run of short-lived goldfish is still a story. If they have lost one lately, 'I am sorry' is enough, and you can move on.
Who do you live with, and how is that going?
Why ask it
Covers partners, roommates, children, parents and cats without assuming any of them, and the second half is mostly answered with a story about the dishes. Keep it for someone you already know a little. On a first meeting it can sound like asking whether they live alone, which people are right to be careful about.
What do you always have in the house?
Why ask it
Good bread, one particular hot sauce, a drawer of candles, a bed made up for guests. Staples are habits you can see, and people enjoy working out what theirs are as they answer.
What is the first thing to go when you get busy?
Why ask it
Sleep, exercise, cooking and answering messages are the common casualties. It is useful to know with a new friend: if replies are what go first, a week of silence from them is about their workload and not about you.
How much of your week do you get to decide for yourself?
Why ask it
A neutral way to ask about freedom and obligation. Shift workers, parents and the self-employed give very different answers. Ask what they do with the hours that are theirs, which is a fair guide to what they would do with more.
When do you do your best thinking?
Why ask it
In the shower, on a run, at four in the morning, at the sink. The answer tells you when not to interrupt them, and whether their good ideas arrive in company or alone.
What has been on your to-do list the longest?
Why ask it
Nearly every list has one item that has survived a dozen rewrites. It tends to be small, slightly embarrassing and easy to laugh about. Now and then it turns out to be something that matters, so do not tease too soon.
What do you still do the old-fashioned way?
Why ask it
A paper planner, cash, an alarm clock that is only an alarm clock, calling instead of texting. People defend these with real feeling, and the reason is often a parent who did it that way or one bad experience with the modern version.
Are you a saver or a spender, and were you raised that way?
Why ask it
Money is easier to talk about as temperament than as numbers. The second half is where it gets interesting, since most people are copying a parent or reacting against one. Better suited to a friend or a relative than to someone you met an hour ago.
What are you saving up for, in money or in time?
Why ask it
Phrased so that it works whether or not they have money to spare: a deposit, a trip, a month off, one empty weekend. Ask how far along they are. Progress is more fun to report than a goal is to state.
Background
How much of the place you grew up in is still in you?
Why ask it
An accent, a way of cooking and a suspicion of big cities are all fair answers. What someone kept from a place, or shed on purpose, covers family and how far they have traveled since, without your asking about either.
Did you move around growing up, or stay put?
Why ask it
People who moved often and people who never left were shaped in opposite directions, and both know it. Ask which of the two they would choose if they had the choice again.
What was your house like when you were growing up: loud, quiet, full of people?
Why ask it
The noise level of a childhood home explains a good deal of what someone finds normal now. It lets them describe a family by its atmosphere, without listing who was in it or who was missing.
Do you have any brothers or sisters, and what were they like to grow up with?
Why ask it
Oldest, youngest, middle and only children all have a theory about what it did to them, and most enjoy explaining it. You will hear how things stand between them now without having to ask. If they were an only child, ask who they played with and what they made of other people's noisy houses.
What did the people who raised you do for work?
Why ask it
Factual, easy, and it places a person quickly: the hours the house kept, what got discussed at dinner, what counted as a proper job. 'The people who raised you' means nobody has to correct you about who that was.
What is the first thing you remember?
Why ask it
Earliest memories are tiny and oddly specific: a carpet, a dog, being lifted up to a window. Nobody can prepare an answer or give a wrong one, which puts two people on level terms.
What is your favorite memory from childhood?
Why ask it
Give them a moment, because the first thing that comes to mind is rarely the one they settle on. It tends to be small: a car journey, a kitchen, one particular afternoon. Ask who else was there. Not everyone looks back on those years fondly, so if they hesitate, add 'or from any age' and let them choose.
Who did you spend most of your time with when you were ten?
Why ask it
It might be a sibling, a cousin, the child next door or a grandparent, and you can picture the household from the answer. Ask where that person is now, which is often a story of its own.
What did you do with your summers as a child?
Why ask it
Camp, a grandparent's house, the family shop, the same street for ten weeks. Summer memories are vivid and, for most people, happy, which makes this an easy way into childhood with someone you do not know well.
What did you get in trouble for as a child?
Why ask it
Talking too much, wandering off, taking things apart to see how they worked. Childhood offenses are often early versions of adult traits, and people enjoy spotting the line between the two.
What were you known for at school?
Why ask it
Everybody was known for something: being tall, being late, being good at math, having a famous older brother. It gets told with affection or with a wince, and either one leads somewhere.
What did you want to be when you were twelve?
Why ask it
Easy to answer, because it commits them to nothing now. The follow-up is whether any of it survives in what they do today, like the would-be vet who works in accounting and fosters dogs. Many people have never made the connection until asked.
What is a family story that gets told every time everyone is together?
Why ask it
Every family has a greatest hit: the burnt dinner, the child left at the gas station, the uncle and the boat. They will tell it well, because they have heard it told fifty times.
Were you close to your grandparents, and what were they like?
Why ask it
Grandparents are an easier way into family than parents, with less at stake. The stories come with food, sayings and houses. If they never knew theirs, that is a short answer you can leave alone.
Who do you take after?
Why ask it
People name a parent, an aunt or a grandfather and then say which part: the temper, the hands, the laugh. Whether it is said fondly or flatly tells you how things stand with that person.
What was the first thing you bought with your own money?
Why ask it
A record, a pair of sneakers, a bus ticket to somewhere forbidden. First purchases are remembered exactly, and you can still hear the pride in them decades on.
What were you sure about at eighteen?
Why ask it
Eighteen is the age of plans and opinions held with total confidence. Asking what they were sure of is friendlier than asking what they got wrong, and it gets you the same story.
What did you study or train in, and would you choose it again?
Why ask it
That choice was mostly made young and on very little information. 'Would you choose it again' is a soft way of asking how they feel about the road since. If they did neither, ask what they taught themselves instead.
What did you leave home for, and how old were you?
Why ask it
Leaving for college, for work, for a person or simply to get out are four different starts to adult life. Some people never left at all, and that answer has its reasons too.
Which place you have lived felt most like home?
Why ask it
It is not always where they grew up or where they live now. Listen for what made it home, whether people, streets or weather, and for whether they are still looking for it.
People
Who is your best friend, and how did the two of you meet?
Why ask it
Meeting stories are easy to tell and usually funny: a shared desk, a terrible apartment, an argument over a parking space. Ask what has kept the two of them close since. Some people have a handful of good friends and no single best one, and saying so is an answer too.
What do you look for in a friend?
Why ask it
Loyalty, a sense of humor, someone who turns up. Whatever comes first is usually something a past friend failed to give or a present one gives in quantity, so ask who they are thinking of. On a date it does double duty, without the weight of asking what they want in a partner.
Who would I meet if I came to your birthday?
Why ask it
A guest list is a map of a life: school friends, work friends, family, the neighbors. It is warmer than asking how many friends someone has, and it shows which group they would put at the head of the table.
Who hears your good news first?
Why ask it
Gets to their people without asking about relationship status or family. Whoever is named is generally at the center of their week, and whether that is a parent, a sibling or a group chat is the better half of the answer.
Do you make friends quickly, or slowly and for life?
Why ask it
People tend to know which they are and to have a theory about why. Either way you know what to expect from them: quick warmth, or a long quiet stretch before you are let in.
Are you better in a big group or with one person at a time?
Why ask it
A fitting thing to ask one to one. You find out whether to invite them to the party or for a walk, and people who prefer one at a time are often relieved to be able to say so.
How do you tend to meet new people these days?
Why ask it
After school and the first job it takes effort, and everyone has either a method or a complaint. You hear about the running club, the school pickup line or the apps, and whether they want more company or have plenty.
Who was the last person you met that you liked straight away?
Why ask it
Shows what wins them over fast: humor, directness, kindness to a waiter. The detail is fresh because it is recent, so ask what the person said or did in the first five minutes.
How do you stay in touch with people who live far away?
Why ask it
Voice notes, a yearly visit, a group chat that never sleeps, or a frank admission that they are bad at it. You find out how much effort goes into people who are not in front of them.
Who do you see every week that you would miss if they moved away?
Why ask it
Picks out the everyday people a life runs on: a colleague, a neighbor, someone at the gym. They rarely get named when you ask about friends, and people are often surprised by who comes to mind.
Who at work would you stay in touch with if you left tomorrow?
Why ask it
Sorts colleagues from friends in one move. With a new workmate the names are the people worth meeting, and no names at all tells you how they feel about the place.
Whose house do you love going to?
Why ask it
A way of asking about a friend through their kitchen table. Whatever makes that house good, the food, the noise, being allowed to do nothing, is what makes this person feel welcome anywhere.
How would your closest friends describe you?
Why ask it
Easier than being asked to describe yourself, because the words can be borrowed. Notice whether they agree with the description. 'They would say I am the organized one, which is funny, because' is where it gets good. Then ask whether their family would say the same.
What do your friends tease you about?
Why ask it
Being teased is a sign of being known, and people repeat the joke against themselves quite happily. You get the trait their friends noticed first. Wait until you know them better before you join in.
Who do you go to when you need a straight answer?
Why ask it
Nearly everyone has one person who will tell them the truth about a haircut, a job offer or a partner. Who it is, and why they trust them, tells you what they count as honesty.
Are you someone people confide in?
Why ask it
People who get told secrets generally know it and have mixed feelings about it. Ask what they think makes others open up to them. The answer is a description of how they listen.
Who do you look up to that you know in person?
Why ask it
Ruling out the famous gets a better answer: a boss, an older sister, a friend who handled a bad year well. The quality they single out is often one they are working on themselves.
If you could have dinner with anyone, living or dead, who would you choose?
Why ask it
An old favorite that still works, because the choice shows what they are curious about. A grandparent they never met, a musician and a scientist are three different evenings. Ask what their first question would be. If they pick someone they have lost, let them tell you about that person and do not hurry on.
Are you close to your family, or is it complicated?
Why ask it
Offering 'complicated' lets someone answer truthfully in two words. If they take it, nod and move on unless they keep talking. Do not ask why.
What is something a friend did for you that you have never forgotten?
Why ask it
Mostly small and practical: a ride at four in the morning, a week on a couch, a meal left on the doorstep. That is what help looks like to them, and it is the kind they are likely to offer you one day.
Which of your friends is least like you, and what do you get from them?
Why ask it
Plenty of people have one friend who makes no sense on paper: the neat one's chaotic friend, the homebody's traveler. The second half matters more. It is what they go looking for in other people because they cannot supply it themselves.
Who would you most like me to meet?
Why ask it
For someone you already like. They pick the friend or relative they are proudest of, and their reasons for the choice are a list of what they value in people. It also assumes there will be a next time, which is no bad thing to signal.
Who do you worry about?
Why ask it
A short question that goes further than it sounds. The answer is a parent getting older, a child, a friend in a bad stretch, and it shows who they feel responsible for. Keep it for someone you have talked to more than once.
Deeper
What would people be surprised to learn about you?
Why ask it
A step past the fun fact. Answers run from a first career as a dancer to a fear of birds, and they decide how far to go. It works best once you have talked for a while, because by then they know what picture you have of them and which part of it to upset.
What do you get asked about all the time, and what do you wish people asked instead?
Why ask it
The first half tends to be their job, their height or where their name comes from. The second half is something they have been waiting for an opening to say, so ask it straight away.
When do you feel most like yourself?
Why ask it
People answer with a place, a person or an activity: on a bike, with a sister, cooking for ten. Ask how much of an ordinary week they get to spend there. The gap between the two is what they would change if they could.
What are you better at than you give yourself credit for?
Why ask it
Saying it out loud takes a small effort, because it sounds like boasting. If you know them a little already, tell them afterward what your answer for them would have been.
What are you most proud of?
Why ask it
Some people answer with an achievement and some with a person, often a child or a younger sibling. Either way, ask what it took, because the effort is a better story than the result. If they cannot name anything, try 'what are you glad you did?', which is easier to answer without feeling boastful.
What have you worked hardest for?
Why ask it
Different from asking what they are proudest of, which invites a trophy. The thing someone worked hardest for might be a qualification, a year sober or peace with a difficult parent, so be ready for a serious answer to a short question.
What is the best advice you have been given, and who gave it?
Why ask it
The giver matters as much as the advice. A line from a grandmother, a coach or a blunt first boss comes with a scene attached, and it is the voice they still hear when they have a decision to make.
What are you patient about, and what are you not?
Why ask it
Nobody is patient across the board. Someone can wait three years for a garden and thirty seconds for a slow walker, and the split shows what they think is worth waiting for. Laugh with them about the impatient half and ask about the patient one.
When did you last surprise yourself?
Why ask it
It needs an actual occasion: the speech they gave, the temper they kept, the invitation they turned down. A recent example means they are still testing themselves, and an example from twenty years ago is its own kind of answer.
If you were twenty again, knowing what you know now, what would you do the same?
Why ask it
The same, not differently. It asks for the decisions they would defend, which is kinder than asking about regret and gets a more considered answer. The regrets tend to follow without being invited.
What makes you trust someone?
Why ask it
The test is mostly unspoken: turning up on time, how a person talks about people who are absent, whether they remember what you said. Whatever they name, you are also being told how to pass it.
What do you do when you do not know what to do?
Why ask it
It asks how someone decides, not what they decided. Lists, long walks, a call to one particular person, doing nothing for a month: the method stays the same from one decision to the next, so it is worth knowing if the two of you ever have to decide something together.
What do you need in order to feel settled?
Why ask it
For some it is a place, for others a person, money in the bank or a plan. Knowing which tells you what unsettles them. A good one for a friend who seems restless.
What do you find yourself daydreaming about?
Why ask it
Daydreams are less edited than plans. A cabin, a different job, an argument they would win this time: it is where their mind goes when nobody is asking anything of it.
What are you still figuring out?
Why ask it
An admission everyone could make and few are asked for. Money, family, what to do next: any answer makes the conversation more equal, especially if you give yours as well.
Do you have a faith, or something that does that job for you?
Why ask it
Religion can feel risky to raise, yet for many people it is the main fact about them. The second half lets everyone answer: the hills, music, a weekly dinner. Ask out of curiosity and bring no counter-argument.
What frightens you more than it probably should?
Why ask it
They can choose between spiders and something that matters. Take whichever they offer at face value. If it is the serious kind, they have decided to trust you, so listen and do not hurry to reassure.
What is the biggest challenge you have come through, and what helped?
Why ask it
For someone who has already told you something personal, not for a first conversation. An illness, a divorce, a year without work: they choose what to name and how much of it to tell. Do not match it with a story of your own. Ask the second half only if they seem willing. It moves the story from what happened to how they got out, which is the part most people are quietly proud of.
What time of year is hardest for you, and what gets you through it?
Why ask it
Many people have a month they brace for: the dark end of winter, a deadline season, an anniversary. Ask gently, because the reason is sometimes a loss, and the second half lets them finish on what helps.
What are you most grateful for at the moment?
Why ask it
'At the moment' steers it away from the stock answers and toward this month: a sister who drove four hours, a job that finally fits, a quiet house. It is a warm question to ask after a hard subject, and a good one for someone who has had a rough year and is starting to come out of it.
What are you hoping for this year that is out of your hands?
Why ask it
Hopes that depend on someone else are carried quietly: a test result, a visa, another person's decision. Being asked can be a relief, and it tells you what to ask after in a few months.
What is a risk you are thinking about taking?
Why ask it
Often there is one on the back burner: a move, a course, a difficult conversation. Ask what is stopping them and keep your own opinion back unless they ask for it.
What is something you would want someone to know about you early?
Why ask it
They choose what goes first. People mention an illness, a child, a hard year, or simply that they go quiet when tired. Whatever it is, they are saying how they would like to be understood, so thank them and do not probe.
Do you think of your life as having a direction, or do you take it a year at a time?
Why ask it
Not everyone has a five-year plan, and it is a relief to be allowed to say so. Planners will show you the map. The rest will tell you what they follow instead: curiosity, people, or the next interesting offer.
What do you want the next few years to look like?
Why ask it
Vague answers are common and fine. A specific one, such as a house with a garden, a business or a move back home, is the thing to remember about them. A good question to finish on, because it leaves the conversation pointing forward.
Making it a conversation, not an interview
Practical guidance for the conversation itself
Choosing from a long list
Read the groups as a depth gauge
Which questions to ask when getting to know someone depends on how far along you are, and the six groups run in that order, from light to searching. Openers and Tastes suit the first few minutes with anyone. Daily life and Background fit once they have started asking you things back. People and Deeper are for someone who has already volunteered something personal.
With someone you just met
Openers is the group for this. Start with what the two of you can both see, the host, the food, whatever they are carrying, and move on to free time or the week they have had once they are talking. Hold the family and money questions for a second conversation. Five easy minutes that end with each of you knowing a name and one true thing about the other is a good result.
On a date, or with someone you like
Stay mostly in Openers, Tastes and Background, and borrow one from People late on. Keep the work questions short unless they light up. The best questions to ask someone you like have answers you can act on, such as a film they have not seen or a place they keep meaning to try, because that is your reason to suggest meeting again. One Deeper question shows interest. Three in a row is an assessment.
With a new friend
Tastes and People do the most here, because they produce things to do together and names to remember. Note what they recommend and try it. Reporting back on a recommendation is the easiest reason there is to get in touch again.
With a colleague
Start with the work questions in Daily life: the first job, who taught them, what they would keep. Money, family and faith are theirs to raise, not yours. A question that is fine between equals can feel like pressure from someone senior, so if you manage them, ask less and offer more.
With a relative
Background is the group to use, and with an older relative the answers are worth writing down afterward. You will already know the outline, so ask for the detail: the street, the wage, the name of the dog.
How to use a list like this
Two or three questions is plenty
A whole evening needs perhaps three of these, spaced out and followed properly. Choose them beforehand and put the list away. Working through it in order, or reading from a phone, is the fastest way to make someone feel processed.
Follow up instead of moving on
The second question about the same answer is where the conversation happens. When did that start, what happened next and who else was there will nearly always beat a fresh topic.
Answer your own question first when it is a personal one
Going first sets the depth and gives them permission to match it. Asking someone who they worry about while offering nothing yourself reads as an examination.
Match their depth, not your curiosity
If they give short answers to the light questions, the searching ones will not land yet. Wait for the moment when they volunteer something unprompted, then go one step further and no more.
Keeping it comfortable
Let silences sit
A pause after a real question mostly means they are thinking, not stuck. The better answers tend to arrive just after the point where it is tempting to rescue them, so wait a beat longer than feels natural before you fill it.
Notice the questions they return
If they ask your question back, answer it properly and at about the length they did. If they never ask anything back, they may be shy or they may be done for the day. Offer something about yourself unasked, and if that gets nothing either, wind things down kindly.
Take a no gracefully
If a question is met with a joke or a change of subject, that is an answer. Accept it visibly and do not circle back later in a different form.
What makes these fall flat
Asking what you already looked up
If you have seen their profile or their employer's website, say so. 'I saw you used to live in Lisbon, what took you there?' is honest and gets a better answer than pretending not to know.
Turning their answer into your story
Matching an answer with one of your own is friendly. Taking over with a longer one is not. Give your version in a sentence or two and hand the conversation back with a question about theirs.
Scoring the answers
If you catch yourself checking answers against a list of what you want in a friend or a partner, they will feel it. You are there to find out who they are. Deciding what you make of it can wait until you are home.
Questions that pin down where someone is
With someone you have only just met, leave alone the exact address, whether they live alone and when the house is empty. It works the other way too: you can answer 'over on the east side' and move on, and anyone worth knowing will let you.