Interesting Questions to Ask
For anyone who wants interesting questions to ask someone: a date, a friend, a colleague or a person they have just met. These are questions whose answers are interesting to hear, whether you are asking a girl, a guy or a whole table: the classics (the dinner guest, the superpower, the bucket list), then odd specifics, opinions with something at stake and things people have changed their mind about. The 141 questions are in six groups (Starters, Odd specifics, Opinions, Changed minds, Know-how and What if). Each group opens with the ones everybody knows, and every question has a note on what to listen for, what to ask next or when to leave it alone.
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The questions
Each question, and why to ask it
Starters
What is something about you that most people would never guess?
Why ask it
The usual answers are a past life (a year in a band, a degree in something unrelated) or a skill that does not fit the first impression. They choose what to reveal, so it is safe with someone you met an hour ago. Ask who does know, and how those people found out.
What is the best trip you have ever taken?
Why ask it
Expect a place name first and the real answer second: who they were with, how old they were, what went wrong and became the story. A weekend two hours from home can beat a month abroad, so say so if they hesitate. Then ask which single day of it they would repeat.
What did you want to be when you grew up?
Why ask it
Most people have an answer ready, and it is usually a job seen from a child's height: vet, pilot, the person who drives the garbage truck. The distance between that and what they do now is the conversation. Ask what the child would make of their real job, and whether any piece of the old plan survived.
What is the best piece of advice anyone has ever given you?
Why ask it
The advice itself is often plain: sleep on it, write it down, ask for the money. Who said it and when is what makes it worth hearing, so ask for both, and then ask when they first actually followed it. If only bad advice comes to mind, take that: there is a question for it under Opinions.
What is at the top of your bucket list?
Why ask it
One item is better than the whole list, because they have to choose. Listen for whether it is a place, a skill or a person they want to see again. The kind follow-up is practical: what would the first step be, and what has been in the way? Do not push if the obstacle is money or health.
What is the last thing that made you laugh until it hurt?
Why ask it
Retold jokes rarely survive, and that is half the fun: watch them try to explain why it was funny and start laughing again. You learn their sense of humor faster this way than by asking them to describe it. Who they were with is usually part of the story, so ask.
What is your happiest memory from childhood?
Why ask it
Ask for one scene and not a summary: a kitchen, a car ride, a particular summer afternoon. The details that come back, such as who was there and what was on the radio, tell you what home felt like at its best. Not everyone had an easy childhood, so if the pause is long, offer 'or any good day from back then' and take whatever they give you.
What are you proudest of having done?
Why ask it
Leave room for something no certificate was issued for: a hard year survived, a younger sibling helped through school, a fence built straight. People tend to play it down in the first sentence, so ask how long it took and who else knows what it cost. Do not follow it with a bigger one of your own.
What is the last thing you searched for that you had no real need to know?
Why ask it
A search nobody asked them to make is easy to remember and costs nothing to admit. The subject is where their mind goes when it is off duty: shipwrecks, an actor's age, how zippers work. Get them to tell you what they found out, since you probably do not know it either.
What have you been telling everyone about lately, whether they asked or not?
Why ask it
It goes straight to whatever has their attention this month: a show, a recipe, a theory about the neighbors. They have told it a few times already, so it arrives in good shape. If nothing comes to mind, 'what was the last thing?' usually finds one.
What small everyday task do you have a strict system for?
Why ask it
The dishwasher, a suitcase, the order things go into a sandwich: whatever it is, they believe their way is simply correct, and that is what makes the explanation fun. Let them finish the whole system before you argue with any of it.
What is the best conversation you have had with someone whose name you never learned?
Why ask it
A seatmate on a long flight, a shopkeeper on a trip, a person at a bus stop who said one sentence at the right moment. The story is usually warm without being heavy, and short enough for a first conversation. A good second question is what they would say if the two of them crossed paths again.
What was the first thing you were completely obsessed with?
Why ask it
Dinosaurs, one band, horses, a single video game: childhood obsessions are remembered in absurd detail. See how much of it they can still recite. Sometimes there is a straight line from that obsession to their job or their bookshelf, and they enjoy spotting it.
What is the last thing you stayed up too late for?
Why ask it
A book, a match in another time zone, a long phone call, one more episode. What a person will trade sleep for is a quick read on what has hold of them this month. If the answer is a work deadline, sympathize and ask for the last time it was by choice.
What are you oddly competitive about?
Why ask it
Board games, parallel parking, step counts, finishing the crossword before a sibling does. 'Oddly' lets them admit to something small and slightly embarrassing. If you turn out to share it, you now have a rivalry, which is a fine way to start.
What is the most recent photo on your phone that is not of a person?
Why ask it
The answer takes seconds to find: a parking level, a label to remember, a strange cloud, somebody's cat. Photos taken as notes say as much about a week as the pretty ones do. Let them choose what to show, and skip this where phones on the table would be rude.
What is the oddest job you have ever been paid to do?
Why ask it
A day in a mascot suit, a night counting cars at an intersection, a week stuffing envelopes. It is kinder than 'what do you do', which matters when work is a sore subject. The worst hour of the job tends to be the best part of the story.
What did you get really into for a few months and then drop?
Why ask it
An abandoned hobby is easier to laugh about than a current one, so the telling is relaxed. The gear is often still in a closet. Why they stopped is the part worth hearing: boredom, cost, a bad teacher or just winter.
What cheap thing do you own that does its job better than the expensive version?
Why ask it
People are proud of these finds and rarely get an opening to mention them: a particular pen, a flea-market pan, drugstore headphones. Expect a short, heartfelt product review. You may also leave knowing what to buy.
Which of your possessions gets the most comments from visitors?
Why ask it
Visitors have already picked out what is unusual about their home, so the person does not have to guess what you would find interesting. It might be a strange lamp, a wall of records or a plant that has taken over the window. The object nearly always arrived with a story, and sometimes with an argument.
Where is the most interesting place you have ended up by accident?
Why ask it
'By accident' removes any need to have traveled far. A wrong train or a canceled plan counts, and so does a wedding they wandered into or a town where they waited three hours for a bus. Find out whether they ever went back on purpose.
What do you do differently from almost everyone you know?
Why ask it
It lets a person show a quirk on their own terms, with the reasoning attached: no phone in the bedroom, dinner at five, the same breakfast for ten years. If they draw a blank, ask what a houseguest would find strange.
What is something good that almost nobody you know has heard of?
Why ask it
A band, a noodle place, a podcast, a walking trail, a writer. Being the one who knows is a pleasure, and the pick shows where their attention goes once it leaves the popular stuff. Some people will not give up a favorite quiet spot, which is fair: take their second choice.
What do you make from scratch that most people just buy?
Why ask it
The reason is the real answer here, whether thrift, taste, stubbornness or a relative who taught them. It could be bread, birthday cards, shelves or their own haircuts. First attempts are worth hearing about because they rarely went well.
What story does your family tell about you that you do not remember happening?
Why ask it
They have heard it so often that they tell it well, including the parts that have clearly grown over the years: the toddler who bit the dentist, the four-year-old who walked out of the store alone. Whether they believe it is a fair thing to ask.
What were you doing the last time you completely lost track of time?
Why ask it
Whatever swallowed three hours unnoticed is what truly absorbs them, and it is not always the hobby they would put on a form. If the honest answer is scrolling on a phone, laugh with them and ask for the time before that.
Odd specifics
What is your most irrational fear?
Why ask it
'Irrational' keeps it light: moths, escalators, calls from unknown numbers, the drain at the deep end of a pool. People usually know exactly when it started, so ask. Laugh with them and never test it. If the thing they name is plainly no joke to them, believe them and move on.
What is your guilty pleasure?
Why ask it
A show they would not admit to at work, gas station snacks, a singer they defend to nobody. The fun is in the confession, so meet it with one of your own and do not tease. Ask how they got started on it and whether anyone else knows. Often one friend is in on it.
What is the weirdest thing you have ever eaten?
Why ask it
Travelers answer with a market stall, and everyone else has a dare from school or a relative's specialty nobody warned them about. Would they eat it again? That is a different question from whether they liked it. One person's weird is another person's Sunday lunch, so stay curious and skip the faces.
Who is the most famous person you have ever met?
Why ask it
'Met' gets stretched to cover a handshake, a held door or pouring them a coffee, and the stretching is part of the fun. Ask what the person was like for those ten seconds and what they wish they had said. Around a table it becomes a contest, and the winner is rarely who you would guess.
What is the most spontaneous thing you have ever done?
Why ask it
A ticket bought at the airport, a haircut on a lunch break, a yes to a job in a city they had never seen. Careful planners have an answer too, and theirs is often told in more detail because it only happened once. Ask what they were supposed to be doing that day.
What do you know by heart that you never set out to memorize?
Why ask it
Whatever stuck without effort was repeated around them for years, so it dates and places them quite precisely: a childhood phone number, an advertising jingle, the safety announcement from an old commute. Have them recite it on the spot.
What is the oldest thing you own, and how did it get to you?
Why ask it
The object matters less than the route it took: a grandmother's ring, a fossil from a gift shop, a coin found in a field. Follow the chain of owners back as far as they can go. If they say they own nothing old, give it a moment, because something usually surfaces.
What is the strangest thing you have ever won?
Why ask it
A raffle ham, a goldfish at a fair, tickets from a radio call-in, a trophy in a sport they played once. If they insist they never win anything, widen it to school prizes and office raffles. Where the prize is now is the natural next question.
What was on your bedroom wall when you were fifteen?
Why ask it
A fast, vivid way into who someone was as a teenager without asking them to describe themselves. Posters, pages torn from magazines, a map, or nothing at all because it was not allowed. Which item would they still put up?
What was the first live show you ever went to, and who took you?
Why ask it
'Who took you' is half the story, because it brings in a parent with their own taste or an older cousin with a car. A relative's band in a church hall counts as much as a stadium tour. See whether they remember what they wore.
What is the first news event you remember, and where were you when you heard?
Why ask it
The answer places someone in time and in a room: a kitchen radio, a classroom television, an adult's face. Comparing first memories works well at a table with several generations. Some first events are tragedies, so let them decide how much to say.
What did your family have its own word for that you later learned had a normal name?
Why ask it
Families invent words for the remote control, leftovers, a particular kind of nap. The story is the moment of discovering nobody else says it, often in front of other people. Trade one of your own to get them started.
What do you own far too many of?
Why ask it
The pile is rarely deliberate, which makes it more honest than asking what someone collects. Mugs, notebooks, tote bags, charging cables and houseplants all count. Get the number, then the number they actually use.
What are you unreasonably picky about?
Why ask it
'Unreasonably' is the permission slip: the pen, the pillow, how done the toast is, which seat at the movies. People get specific and a little heated. It is also worth knowing before you lend them a pen.
What record do you probably hold among the people you know?
Why ask it
It lets someone boast about a thing that is not really a boast: most bones broken, most homes lived in, most times seeing the same band. In a group, put the claim to the others and see if it stands.
What is the longest streak you have ever kept going?
Why ask it
Broken streaks are remembered with real feeling, so find out how it ended, whether it was a daily run, a diary or a weekly call to a parent. If the streak is still alive, the question is what would be allowed to break it.
What is the most unusual place you have ever spent a night?
Why ask it
An airport floor, a ferry deck, a hospital chair, a tent in a backyard, a friend's bathtub. How much sleep was involved is the first thing to establish. There is usually a second story underneath about why they were there at all.
What is the longest line you have ever stood in, and was it worth it?
Why ask it
What a person will wait six hours for says what they care about more plainly than asking outright. A concert, a visa, a limited-run doughnut and a roller coaster are very different answers. The 'was it worth it' half is where they get honest.
What is your closest brush with something that made the news?
Why ask it
Small brushes are as good as big ones: two streets from a famous event, an elevator shared with a celebrity, a face in the background of a broadcast. If the event was a frightening one, let them tell it at their own pace.
What have you done exactly once and would never do again?
Why ask it
A skydive, a marathon, a silent retreat, karaoke, one particular ferry crossing. 'Never again' stories come with energy because the verdict is already in. The interesting part is whether they are glad they did it the one time.
What is the smallest decision you have made that ended up changing a lot?
Why ask it
People enjoy tracing a job, a city or a marriage back to something tiny, like a seat they happened to take or a later bus. Give them a moment, because the best examples take some thinking.
What is the most niche club, community or corner of the internet you belong to?
Why ask it
A forum for one model of bicycle, a local history group, a chat about a canceled show. What the members argue about is usually something no outsider could guess, so ask. Do not mock it: they are showing you somewhere they feel at home.
What is the last thing you fixed yourself instead of replacing?
Why ask it
You learn whether they reach for a screwdriver or a video first. A zipper or a wobbly chair is as good an answer as a car engine, and a repair that failed is the better story, so find out how it ended.
What have you put more hours into than anything else outside work, and what do you have to show for it?
Why ask it
The honest answer might be a sport, an instrument, a garden or one video game. The tail of the question is deliberately cheeky, and people rise to it. Take the answer seriously even if they play it down, because that many hours means it mattered.
What route do you know so well you could walk it with your eyes shut?
Why ask it
Have them describe it turn by turn and watch how much comes back: the walk to a school, to a grandparent's house, to a first job. It is a gentle way into a period of their life without asking about it directly.
Opinions
What is your biggest pet peeve?
Why ask it
Slow walkers, speakerphone in public, people who open with 'no offense'. How fast the answer comes tells you how long they have been holding it in. Ask whether they have ever said anything to an offender. Then check, quietly, whether you do it yourself.
Do you think there is intelligent life somewhere else in the universe?
Why ask it
Nobody at the table can settle it, which is why it works: people reason out loud from numbers, from faith or from films they saw at twelve. The second half is better. Would they want to know for certain, and would they want to be the one who made contact? If it goes well, ghosts and fate are the same kind of question.
What activity do you suspect most people only pretend to enjoy?
Why ask it
The pick is often something they have been dragged to more than once: camping, networking events, jazz, long brunches. If it happens to be your favorite thing, defend it cheerfully, because the disagreement is the fun part.
What book, film or show did everyone rave about that left you cold?
Why ask it
A good answer names the thing and says what was missing, which tells you what they want from a story. Did they finish it? If you loved it, say so and let them explain what you got wrong.
What is better now than it was twenty years ago, and what is plainly worse?
Why ask it
Asking for both halves stops the answer from turning into pure nostalgia or pure cheerleading. Listen for whether they reach for gadgets, manners, food or prices. Someone under thirty can answer from what they have been told, which is its own conversation.
What piece of advice gets repeated everywhere that you think is simply wrong?
Why ask it
Follow your passion, never go to bed angry, the customer is always right. A good answer comes with the time the advice failed them. Then find out what they would put in its place.
Which of your views would lose a vote among your own friends?
Why ask it
The friends are real, so you get a view they have already had to defend. It need not be political: money, parenting, cities and sleep all qualify. Ask how the argument usually goes, and do not restart it yourself unless they clearly want that.
What do people spend years chasing that you think is not worth having?
Why ask it
A title, a big house, a follower count, a perfect lawn. Saying what you have decided not to want is harder than saying what you do want, so give it time. The follow-up that matters is whether they ever chased it themselves.
If you could add one subject to every school's curriculum, what would it be and what would you cut to make room?
Why ask it
The addition comes quickly: cooking, tax forms, arguing well, first aid. The cut is the hard part, and it is what turns a wish into an opinion. If there are teachers at the table, let them go last.
Is it better to be very good at one thing or decent at a lot of things?
Why ask it
People answer from their own life, so you learn which of the two they think they are. Are they happy with that, or do they envy the other kind? It is a friendly argument with no right answer.
Which invention would we be better off without?
Why ask it
Expect leaf blowers, reply-all, the open-plan office and the alarm clock. Push for what would be lost as well, because every invention has somebody who depends on it. Petty answers are as good as serious ones here.
Which job deserves far more respect than it gets?
Why ask it
The job named is often one they have done or watched a parent do, so a personal story is close behind. Ask what the rest of us fail to see about it. It suits a table of people from very different kinds of work.
What should cost more than it does, and what should be free?
Why ask it
Two prices to set, so the answer is a small manifesto. The reasoning is usually about fairness or about waste, and it helps to notice which. If it drifts into party politics and the table tenses, steer back to the specific thing they named.
What counts as rude now that was perfectly normal when you were growing up?
Why ask it
Calling without texting first, dropping in unannounced, commenting on someone's weight. The answer depends on age and on where they grew up, so it travels well across a mixed table. Do they think the change is an improvement?
Which matters more in the long run: talent or stubbornness?
Why ask it
Whichever side they take, the proof is a person: the gifted friend who went nowhere, or the plodder who ended up running the place. Ask which of the two they have more of. The answer can be a quiet verdict on their own career, so let them say that part themselves.
Which famous place let you down, and which one turned out better than its reputation?
Why ask it
Naming a letdown takes a little nerve, since somebody present may love the place. Asking for a pleasant surprise as well keeps the answer from becoming a list of complaints. What they had pictured before they arrived is often funnier than what they found.
A friend shows you a plan you think will fail. Do you say so?
Why ask it
The scenario forces a choice between honesty and loyalty that abstract questions about honesty let people dodge. Change the facts and ask again: what if the friend has already quit the job or paid the deposit? Then turn it around and ask what they would want from a friend.
What technology do you refuse to use, and what would change your mind?
Why ask it
The refusal usually rests on one principle or one bad experience, and it is worth finding out which. It could be a smart speaker, a certain social app, a fitness tracker or a robot vacuum. What it would take to change their mind tells you whether the position is firm or just a habit.
Which compliment do you think is secretly an insult?
Why ask it
'You look well', 'that is so brave', 'you are so organized'. The answer often traces back to a remark that was once made to them and stung. It doubles as a warning about what not to say to this person.
Would you rather live somewhere beautiful and far from your people, or somewhere dull and close to them?
Why ask it
Plenty of people have faced a version of this for real, so answers come from experience and not from daydreams. Would they have said the same ten years ago? Tread lightly with anyone who lives far from family and did not choose to.
What custom from another country, family or era should the rest of us adopt?
Why ask it
An afternoon nap, shoes off at the door, long Sunday lunches, handwritten thank-you notes. People pick something they have seen work up close. The obvious follow-up is what stops them from doing it already.
What do people get wrong about your generation, and what do they get right?
Why ask it
They get to push back and then concede something, and the concession is where the honesty is. It works best with more than one generation at the table, each answering in turn. Keep it good-humored, since it tips into grievance easily.
What is the best age to be, from what you have seen so far?
Why ask it
Some name an age they have passed, some the one they are, and a few name one still ahead. Each of those is a different outlook on their own life. What did that age have, or what will it have, that the others lack?
Changed minds
What would you tell your younger self if you had one minute with them?
Why ask it
One minute forces a single message, and it tends to be about a worry, a person or a decision they took too long over. Ask which age they pictured, because people choose very different ones. A good last question is whether the younger version would have listened.
Who has changed the way you think more than anyone else?
Why ask it
A parent or a teacher is the common answer, but it can be a friend who argued with them for ten years or a writer they never met. Ask for the one sentence or habit they took from that person. If the person has died, let them talk as long as they like and do not hurry to the next question.
What did you swear you would never do that you now do without thinking?
Why ask it
The answer is usually funny and a little rueful: bed at nine, a minivan, saying 'because I said so', a sudden interest in gardening. When they first caught themselves doing it is the moment to ask for.
What did you roll your eyes at until you actually tried it?
Why ask it
Yoga, audiobooks, birdwatching, journaling, an air fryer. Admitting it costs a little pride, so pay with one of your own. Somebody usually talked them into it, and that person deserves a mention.
What did you believe for an embarrassingly long time because someone told you once when you were small?
Why ask it
That swallowed gum stays inside you for seven years, that the ice cream truck plays music only when it has sold out, that an uncle was a spy. How old they were when they found out, and who was in the room, is the story. Go around the table with this one.
Who did you dislike on first meeting and end up liking a great deal?
Why ask it
The story shows what puts them off quickly and what wins them over slowly. Some of the best versions are about a person who is now a close friend or a spouse. If that person is at the table, let them give their side.
What did you once take as a sign of intelligence that you no longer do?
Why ask it
A big vocabulary, quick comebacks, good grades, a taste for difficult films, cynicism. What replaced it is the real answer, so ask what they look for now. They may be describing a specific person without naming them, and you can leave it that way.
What album, novel or movie did you dismiss the first time and come around to later?
Why ask it
Taste shifts with age and circumstance, and people can often say exactly what shifted: a breakup, a move, having children. What made them give it a second try? It pairs well with asking what they once loved and can no longer stand.
What word or phrase did you once hate that you now catch yourself saying?
Why ask it
A small, safe confession, whether it is office jargon, a parent's catchphrase or slang from someone much younger. The source is usually a person they spend a lot of time with, so ask who.
What did you think was boring until someone explained it properly?
Why ask it
The credit usually goes to one teacher, friend or presenter, and what that person did differently is the thing to ask about. It works for history, baseball, wine, statistics or opera. The answer is also a hint about how this person likes to be taught.
What were you once embarrassed by that you are now a little proud of?
Why ask it
An accent, a hometown, a middle name, a parent's old car, being the kid who liked math. The turn often came when they left the place where it was embarrassing. Go gently, because some of the old feeling may still be there.
What did a trip, a job or a roommate change your mind about?
Why ask it
Each of the three puts a person up close to a way of living they had only held opinions about: sharing a kitchen with someone tidy, working nights, a month where dinner is at ten. Let them choose which one to answer, and ask for the before if they skip straight to the after.
Which teacher or boss seemed unreasonable at the time and makes sense to you now?
Why ask it
This one tends to arrive once people have had to manage or teach someone themselves. What would they say to that person today? If the verdict is that the person really was unreasonable, that is a fair answer too.
What did you once spend real money on that you would not pay for today?
Why ask it
The shift shows how their priorities have moved without anyone giving a speech about values. It might be concert tickets, sneakers, nights out or a gym they never visited. Where the money goes now is the second half of the answer.
What did you believe about money growing up that you have since revised?
Why ask it
That all debt is shameful, that talking about pay is rude, that a house is always the safe choice. The first belief came from home, so this touches family as well as money. Keep it to ideas: do not ask for figures, and do not treat their conclusion as advice.
What have you become stricter about as you have gotten older, and what have you relaxed about?
Why ask it
Asking for both keeps it from sounding like a complaint about aging. You might hear that bedtime and punctuality have tightened while clothes and other people's opinions have loosened, or the exact reverse. People in their twenties have answers too.
What were you overruled on that turned out better than your own plan would have?
Why ask it
A house, a vacation, a baby's name, a hire: they argued, lost, and then had to watch the other choice work. It takes some grace to tell, which says something about the teller. Did they ever admit it to the person who won?
What is the last opinion someone argued you out of, and what did the trick?
Why ask it
What did the trick is the interesting part: evidence, patience, a joke, or simply being someone they trust. It tells you what kind of persuasion works on this person. Thinking of one takes a moment, so wait.
What is the best case you have heard for something you still disagree with?
Why ask it
Stating the other side well is rarer than having an opinion. A thoughtful answer comes from someone who has listened as well as argued. If they cannot think of one, notice it and do not point it out.
Which of your opinions do you hold less firmly than you sound when you say it?
Why ask it
This is for the view someone states loudly out of habit and privately doubts. Admitting it is disarming and makes the rest of the conversation more honest. Offer yours first to show it is safe.
What are you sure about, and what evidence would actually change your mind?
Why ask it
Naming the certainty is easy. Naming the evidence is where people have to stop and think, and 'nothing would' is informative too. Pick this for someone who enjoys ideas, and skip it if the mood is light.
What rule at work or school did you think was pointless until you saw what happens without it?
Why ask it
Sign-in sheets, checklists, uniforms, the meeting nobody wanted. The story is usually about the day the rule was skipped and something went wrong. It is a good one among colleagues, who will each have a candidate.
Know-how
What is your most useless talent?
Why ask it
Saying the alphabet backwards, naming a song from its first second, folding a fitted sheet properly. 'Useless' takes the pressure off, and most of these can be demonstrated on the spot, so ask for a demonstration. Then ask how they discovered it, since nobody sets out to learn one.
What does your job let you see that most people never get to?
Why ask it
Every job has a back room: the kitchen during service, the inside of other people's houses, the numbers behind a price. It beats 'what do you do' because it asks for the interesting part directly. For students, parents at home and retired people, say 'your days' in place of 'your job'.
What does everyone assume about your line of work that is not true?
Why ask it
Nurses, teachers, programmers and real estate agents all have a ready answer, usually with some heat behind it. You come away knowing what not to say to them. Where they think the mistaken idea comes from is a good second question.
What trick from your work or hobby would be useful to anyone?
Why ask it
How a chef holds a knife, how a mover lifts, how an editor cuts a sentence. Being asked for expertise is flattering, and you leave with something you can use. If the setting allows, get them to show you.
What are you the first call for among the people you know?
Why ask it
Fixing phones, reading contracts, advice after a breakup, a ride to the airport. The answer is the role they play among their own people, and their tone tells you whether they enjoy it or have had enough. Then ask what they wish people called them about.
What looks easy from the outside and is actually very hard?
Why ask it
They will answer from experience: parallel parking a van, making a good omelet, keeping a small shop open. The hidden difficulty is what you want them to explain. It may double as a complaint about people who assume it is simple, and that is fine.
What looks intimidating and turns out to be easy once someone shows you?
Why ask it
Changing a tire, baking bread, reading a train timetable in another language, asking for a bill to be lowered. It is an encouraging question and can end with an offer to teach you. Who showed them is worth a sentence too.
What do you notice right away, because of your job or hobby, that other people walk past?
Why ask it
A typographer sees bad spacing on every menu, a builder sees the crack above the door, a musician hears the flat note in the grocery store. Can they ever switch it off? Look around the room together and have them tell you what they see.
What is the most common mistake beginners make at the thing you know best?
Why ask it
People who know a subject well answer this instantly and with feeling. Listen for whether the mistake is about technique or about patience. If you are a beginner at that thing, you have just had a free lesson.
What tool do you rely on for your work or hobby that most people have never heard of?
Why ask it
A bone folder, a seam ripper, a torque wrench, one obscure spreadsheet function. Have them explain what it does and what the job was like before they had it. Expect real affection: a good tool gets talked about like a good colleague.
What is the most expensive mistake you have seen made in your line of work?
Why ask it
Told about someone else, it comes without embarrassment: the wrong tile ordered for a whole floor, a misplaced decimal point, a deleted folder. How it was caught and who had to make the phone call are the details to ask for. Do not push for names or for the employer.
What do you avoid buying or ordering because you know how it is made or run?
Why ask it
Anyone who has worked in a kitchen, a store, a hotel or a call center carries a private list. Take it as one person's experience and not as a rule about every business. Balance it by asking what they would buy or order with confidence.
What word from your work or hobby should the rest of us borrow?
Why ask it
Trades and hobbies have words for things everybody experiences and nobody else can name. Sailors, climbers, bakers and coders are good sources. Use the word back to them before the conversation ends.
What is something about your hometown that only locals know?
Why ask it
The shortcut, the real name for a place, the store that is never open, the thing visitors always get wrong. It works whether the town is famous or tiny. Where would they send you if you had one afternoon there?
What is about to change in your kind of work that outsiders will not notice for years?
Why ask it
People inside a trade often see a shift before it reaches the news. Ask whether they think the change is good, and for whom. With someone who is retired, ask what changed most between their first day and their last.
Who is the best you have ever watched up close at what they do, and what were they doing differently?
Why ask it
A surgeon, a bricklayer, a waiter handling ten tables, a grandmother with dough. The details they noticed are the answer, because they show what this person counts as good work. A nice last question is whether the expert knew how good they were.
How did you learn the thing you are best at: taught, self-taught or thrown in?
Why ask it
The route matters as much as the skill. 'Thrown in' tends to come with a first day that went badly, which is the story to ask for. Given the choice, how would they teach it to someone else?
What can you do that your grandparents would find baffling, and what could they do that you cannot?
Why ask it
What the grandparents could do is the richer part: darning, canning fruit, finding the way by landmarks, getting by in three languages. It opens family history without asking for it outright. Find out whether anyone in the family still knows how.
What do you know enough about to bore a dinner table, and what is the one part that is not boring?
Why ask it
The first half lets them name the subject with a laugh, and the second makes them pick its single best fact, which spares you the other fifty minutes. Tax law, tram routes, sourdough, one football club's history. If the best part really is good, ask for the second best.
What if
If you could have dinner with anyone, living or dead, who would you choose?
Why ask it
The best-known question of its kind, and still good if you ask the second half: what would they want to have found out by dessert? Some pick a hero and some pick a grandparent they never met, and those are very different dinners. If they choose someone they have lost, slow down and let them tell you about that person.
If you could have any superpower, which would you pick?
Why ask it
Flying and invisibility are the stock answers, and the reason is what tells people apart: one wants to skip traffic, another wants to hear what is said after they leave the room. Ask what they would do with it in the first hour. In a group, let the others point out the drawbacks.
If you won the lottery tomorrow, what is the first thing you would do?
Why ask it
'The first thing' keeps it from becoming a shopping list. Some people would call a relative, some would clear a debt, some would tell nobody for a month. Ask whether they would keep working. It pairs well with the question further down about giving a million dollars away, because the two answers rarely match.
If you could live anywhere in the world, where would it be?
Why ask it
Listen for whether they name somewhere they have been or somewhere they have only pictured. Then make it real: which neighborhood, what work, who comes along? Quite often the answer turns into home with one thing changed, and that one thing is worth knowing.
If you were stranded on a desert island, what three things would you want with you?
Why ask it
Rule out a boat and a working phone before they start. Practical people take a knife, a pot and a tarp, and others take a guitar, a photo album and the dog. Ask what the third item is for, because that is usually where survival gives way to comfort.
If your life were made into a film, who would play you?
Why ask it
The casting says how they see themselves, or how they hope to be seen, and friends at the table will have firm views on the gap. Ask what kind of film it is and which year of their life gets the most screen time. Keep any alternative casting kind.
What would you try if you knew you could not fail?
Why ask it
It takes away the usual excuse, so the answer is often something they could in fact begin: a business, a novel, a difficult conversation with a relative. Ask what the smallest version of it would look like. If they laugh it off with 'rob a bank', smile and ask again for the real one.
What would your perfect day look like, from the time you wake up?
Why ask it
Have them go through it hour by hour: where they wake, who is at breakfast, what happens after lunch. Perfect days are often more modest than you would expect, with good weather and no clock. Notice who is in it. It suits someone you like, because you come away knowing what to plan.
If you could know one true fact about the world fifty years from now, what would you ask for?
Why ask it
One fact is a tight limit, so people have to decide what they most want to know: the climate, their grandchildren, their team. The choice is a map of what they are hopeful or worried about. Would knowing change anything they do now?
If you could be a fly on the wall for one conversation in history, which would it be?
Why ask it
History fans go for a treaty or a trial, and others pick the day their parents met or the rehearsal where a favorite band wrote its best song. Both kinds are good. Ask what they expect they would hear.
If you had to live in a different century, which one would you pick and what would you do for a living?
Why ask it
The job is what makes people think, because they have to place themselves somewhere ordinary and not on a throne. Someone will bring up dentistry. What would they miss within the first week?
If you could have one question answered truthfully by anyone alive, who would you ask and what?
Why ask it
Some choose a politician or a chief executive, and some choose their mother. Either way you learn what they think is being kept from them. Do not press if the person they name is close to home.
If you could send one object from today back to yourself at fifteen, with no note, what would you send?
Why ask it
With no note allowed, the object has to do the explaining, which is harder than it sounds. A set of house keys, a photo, a concert ticket and a paid-off bill each carry a different message. Ask what the fifteen-year-old would have made of it.
If you were dropped in a city where you knew nobody and had a month to build a life, what would you do in the first week?
Why ask it
The first move is the tell: a gym, a choir, a five-a-side game, a place of worship, a cafe to become a regular at. It is how they would go about making a home anywhere. Anyone who has moved for work or school will answer from memory.
If you ran your town for a year with a real budget, what would you fix first?
Why ask it
A pothole, a dangerous intersection, a library with short hours: the answer is local and concrete. It is a civic opinion without party politics, which keeps it safe across a mixed table. Get the second fix as well, because the first is often one the whole table shares.
If you had to give away a million dollars by Friday, with none of it going to people you know, where would it go?
Why ask it
The deadline and the ban on friends force a real decision about causes, places and strangers. Not knowing where to start is a common first reaction, and worth talking about in itself. One place, or split between several?
If you had to bet your savings on one prediction about the next ten years, what would it be?
Why ask it
Savings on the line separates what people say they expect from what they actually believe. Answers run from house prices to which sport will fade. Ask how sure they are in rough odds, and keep it a game: nobody here is giving a tip.
Would you take a seat on a one-way trip to Mars? What about a return trip that took ten years?
Why ask it
The first question divides a room in seconds. The second is harder, because it prices adventure in missed birthdays. Ask who they would need permission from.
Would you rather be famous now and forgotten later, or unknown now and remembered in a hundred years?
Why ask it
It asks what recognition is for: enjoying it or leaving something behind. Anyone who writes, builds or makes things may take longer over it. If they choose the second, ask what they would want to be remembered for.
If you had to spend a year with no internet, what would you do with the time, and what would be the hard part?
Why ask it
Books, a garden, an instrument: the plan for the time is the fantasy. The hard part is the honest bit, and it tends to be about work, maps or keeping up with one particular person. Would they take the year if it were offered?
If you could keep only three apps on your phone, which would survive?
Why ask it
Quick, concrete and more telling than it looks. If maps and messages take two of the slots, the third is the one to ask about. Someone who keeps the camera and someone who keeps the banking app want different things from a phone.
If you had to change your first name tomorrow, what would you choose?
Why ask it
Some have had a name in reserve since childhood and others are horrified by the idea. It leads naturally to what their parents nearly called them. Skip it with anyone who has changed their name for reasons they may not want to go into.
If you had to live on a boat, in a van or in a lighthouse for a year, which would you pick?
Why ask it
Three kinds of solitude: moving on water, moving on land, or staying put. The reasoning matters more than the choice, so ask what an ordinary Tuesday would look like. Two people who live together may be surprised by each other's answer.
If you were given one room in a museum to fill with anything you liked, what would the exhibit be?
Why ask it
The answer is whatever they think deserves more attention than it gets: old radios, their grandmother's recipes, the history of a local team. Ask what the centerpiece would be. If the mood is light, ask what the gift shop would sell.
If you could put one thing back the way it was when you were a kid, what would you restore?
Why ask it
A store that closed, Saturday morning cartoons, a field that is now a parking lot, the way a certain candy bar used to taste. It is nostalgia with a decision in it. Would today's kids thank them for it?
If an expert in anything gave you an hour to explain one thing until you truly understood it, what would you pick?
Why ask it
Admitting what you do not understand takes more confidence than listing what you do. Answers range from how planes stay up to how their own retirement account works. If someone at the table can explain it, let them try.
Getting an answer worth hearing
Practical guidance for the conversation itself
What makes a question interesting
Start with one everybody knows
The dinner guest, the superpower and the bucket list are familiar because they work: nobody needs them explained and almost anyone can answer. Each group on this page opens with a few of those. The first answer to a familiar question is often one the person has given before, so the notes on them mostly tell you what to ask second: what they would want to find out by dessert, or what the first step toward the bucket list would be.
Ask for one, not a favorite
'What music do you like' gets a category and a shrug. The questions here ask for a single exact thing: the last search, the first live show, the longest line. One real example is easier to produce than a ranking, and it comes with a story attached.
Give the question a cost
An opinion is only interesting when something is at stake. That is why the Opinions group asks what you would cut from school to make room, which of your views would lose a vote among your friends, and whether you would tell a friend their plan will fail. If everyone at the table would give the same answer, the question was too easy.
Ask for the before and the after
Changed minds works because a change has two ends. When someone tells you what they think now, ask what they thought before and what moved them. The cause tends to be a person, a job or a place, and that is the part worth hearing.
Pick for the person, not from the top
Choose two or three questions you would honestly like to hear this particular person answer. Starters, Odd specifics and Know-how are safe within minutes of meeting someone. Opinions and What if go better once you have laughed together, and the later Changed minds questions suit one person at a time.
Asking a girl, a guy or a whole table
Someone you like
There is no separate list of interesting questions to ask a guy and another for a girl: the same ones work for both. What should change your choice is how well you know them and where you are. Early on, draw from Starters and Odd specifics, where every answer is a small story about them. Hold the Opinions until you can both enjoy disagreeing, and when you do disagree, treat it as a good sign and not as something to smooth over.
Over text
Short, concrete questions travel best in a message: the strangest thing they have won, what they own too many of, the most recent photo on their phone that is not of a person. Send one at a time with your own answer attached, so it reads as a trade and not a quiz. Questions with two halves, and most of Changed minds, are better saved for when you can hear each other.
A table of friends or family
Ask one question and go around, starting with whoever will enjoy it most. Opinions and What if are made for this, since half the fun is other people objecting. The first news event and the generation question are best with several ages present. Let anyone pass without comment.
Colleagues and people you have just met
Know-how is the group for this. Asking what someone's job lets them see, or what beginners get wrong, is flattering and stays professional. Leave out the money questions, and do not ask about the most expensive mistake at their own workplace, where the answer may be about someone in the room.
After they answer
Get the example
First answers are often general. 'When was that?' or 'what happened the last time?' turns an opinion into a story. Many of the notes on this page name the detail to go after, such as how a streak ended or who was in the room when a childhood belief fell apart.
Disagree and stay curious
When you think they are wrong, say so lightly and ask what you are missing. An opinion everybody agrees with is over in a sentence. Stop well before either of you is trying to win.
When the answer is 'I do not know'
Some of these need a minute: the smallest decision that changed a lot, the last opinion someone argued them out of. Say 'take your time' and mean it, or answer first yourself so they have an example to work from. If nothing comes, drop it without comment and try a Starter.
Have your own answer ready
Before you ask, check that you could answer in a sentence or two. If you cannot, the question may be too hard to spring on someone. When they turn it around on you, keep your version brief and hand the conversation back.
How a good question goes flat
Several in a row
Three questions with no comment in between feels like a survey. Stay with one answer until it runs out. Two questions from this page, followed up properly, are enough for a long dinner.
Setting up your own speech
If you ask which piece of advice is wrong only so you can give your own answer, they will hear it. The same goes for asking which opinion they were last argued out of while hoping to be named. Ask when you are ready to be surprised.
Letting it turn heavy
These questions are meant to be interesting, not searching. A few can brush against something painful: a first news memory, living far from family, a name someone had reasons to change. When that happens, listen, do not dig, and move to a What if once the moment has passed.
Reading from the screen
A question chosen for the person sounds different from one read off a phone. Pick yours beforehand and put the page away. Once they are telling you about a mascot suit or the town they grew up in, the list has done its work.