Interesting Questions to Ask a Guy
Interesting questions to ask a guy when you want more than 'fine' and 'not much' back, whether he is a date, a boyfriend or a new friend, and whether you are talking in person or over text. The 88 questions are in six groups, in the order you would use them: Stories, Obsessions, Opinions, What if, Changed his mind and People. The note under each one says what kind of answer to expect and gives the follow-up that gets you past the first short one.
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The questions
Each question, and why to ask it
Stories
What's the wildest thing you've ever done that you'd happily do again?
Why ask it
The first answer is usually a headline: a cliff jump into a lake, a road trip decided on at midnight. 'Would do again' screens out the ones he regrets, so ask whose idea it was and who else was there, and the headline turns into a story.
What's the worst job you've ever had, and what's the best story from it?
Why ask it
Bad jobs make good stories, and he has had time to polish this one. A guy still in school can answer with a chore, a volunteer shift or a group project. Ask about the worst customer or the worst boss and he will do the voices.
Where have you been that you keep wanting to go back to?
Why ask it
This is the travel question with a pull in it: he has to pick the place that stayed with him, which may be a lake two hours away and not the big trip. Ask what he would do on the first morning back.
What can you do that would surprise people who think they know you?
Why ask it
Hidden talents come out here: juggling, a decent singing voice, backing a trailer into a tight spot. Asking for a demonstration is the obvious next step. If he says 'nothing', ask what his friends would volunteer on his behalf.
What did you do as a kid that your parents still don't know about?
Why ask it
Nearly everyone has one, and enough years have passed that it is safe to tell. Expect a broken window, a secret pet or a bike ride much farther than allowed. 'How close did you come to getting caught' keeps it going.
What's the most trouble you ever got into at school?
Why ask it
A quiet guy's answer can be the surprise of the evening. The crime tends to be small and the punishment out of proportion, which is why he remembers it. Find out whether he would do it again, knowing the price.
What's the luckiest thing that's ever happened to you?
Why ask it
Good luck is easier to talk about than achievement because he does not have to brag. You may get a found wallet, a missed flight that turned out well, or how he met his best friend. Listen for whether he thinks of himself as a lucky person in general.
What's the closest call you've ever had?
Why ask it
He picks the size: a near miss on a bike, a class passed by a single point, a deer on the road. If the story is a serious one, drop the jokes and let him finish it at his own speed.
What's the best night you've had that nobody planned?
Why ask it
Unplanned nights get retold for years, so this one arrives with its details already attached. 'When did you know it was going to be a good one' gets you the turning point. It also gives you his idea of fun, which is handy if you are the one planning next time.
What's the best meal you've ever eaten, and where were you?
Why ask it
The answer is rarely about the food alone. A burger after a long hike or his grandmother's Sunday dinner comes with a place and people, so ask who was at the table.
What's the most out-of-character thing you've ever done?
Why ask it
To answer he first has to say what his character is, so you get his own description of himself for free. The careful guy who once quit on the spot, the loud one who spent a week alone in a cabin: what got into him?
What's the most beautiful thing you've seen with your own eyes?
Why ask it
Give him a moment: it is not a question he gets asked much. It might be a night sky far from any town, a stadium at full volume or a goal he watched from behind the net. Whatever he picks, ask whether he took a photo or just stood there.
What's the farthest you've ever been from home, and what took you there?
Why ask it
Simple to answer, and the second half is where the story is: a school trip, a relative's wedding, a job, a dare. If he has not traveled much, ask where he would point the car with two free weeks.
What's the best present you've ever been given, and who knew you that well?
Why ask it
The gift itself may be modest. What you are after is the person who chose it and what they had noticed about him. It doubles as a hint if his birthday is coming up.
What's the story you always end up telling when you meet new people?
Why ask it
He knows exactly which one it is. Hearing it shows how he likes to be seen: the funny one, the one things happen to, the one who got away with it. Then ask what the story leaves out.
Obsessions
What could you talk about for an hour with no notes?
Why ask it
Only ask when you have time to hear the answer, because a real one runs long. Car engines, one team's trades going back twenty years, how a certain game got made. Your job is to ask the beginner questions he secretly enjoys answering.
What's the last rabbit hole you fell down at one in the morning?
Why ask it
Shipwrecks, how elevators work, the full history of a band he does not even like. The topic matters less than how he tells it. What he was looking up in the first place is worth knowing, since the path from there to the shipwreck is usually the funny part.
Which movie have you seen more times than any other, and what keeps you going back?
Why ask it
Different from his favorite, and more revealing: this is the one he puts on when he is sick or cannot sleep. Have him quote a line. If you have not seen it, you now have a plan for an evening.
What game, of any kind, have you put the most hours into?
Why ask it
'Of any kind' lets in chess, darts, pickup basketball and a board game his family takes too seriously, as well as anything with a controller. 'What are you like when you lose' is the follow-up, and his account of that is usually honest and funny.
What do you know a strange amount about for no good reason?
Why ask it
Everybody has a subject like this, whether it is sharks, Roman roads, sneaker releases or one particular war. Ask for the single best fact. If he hesitates, he is deciding whether you want the short version, so say you want the long one.
Whose career do you follow closely: an athlete, a musician, a director, anyone?
Why ask it
A guy who tracks one person's every move has picked them for a reason. Find out when he started following them and what he would say if they met. It works just as well when the answer is a chef or a streamer.
What's the best thing you've ever built, made or fixed?
Why ask it
A bookshelf, a computer, a song, a go-kart that lasted one afternoon. Guys who say little about themselves will often talk at length about a thing they made. Ask what went wrong along the way and whether it still exists.
If you had to teach a class tomorrow, what would it be on?
Why ask it
A way of asking what he is good at that does not sound like an interview. Follow with 'what would the first lesson be', and if he likes the idea, let him teach you five minutes of it on the spot.
What album would you make me listen to from start to finish?
Why ask it
Music taste is personal, so treat the answer with some care even if it is not your thing. Ask which track he would be nervous about you hearing. Then go and listen, because reporting back is a ready-made next conversation.
What did you collect as a kid, and where is it all now?
Why ask it
The collection is probably in a box at a parent's house, and he can still tell you which card, coin or rock was the prize of it. Follow it with 'what do you collect now', where ticket stubs, sneakers and saved playlists all count.
What would you spend a ridiculous amount of money on without feeling bad about it?
Why ask it
Not the sensible answer about a house. This is concert tickets, a particular car, kitchen knives, sneakers, the best seat at one game. You learn what he values over saving, and how long he has been pricing it out.
What's the best thing you've watched, read or played this year, and what made it that good?
Why ask it
The second half is the question. 'It was just good' is a first answer, so ask for the scene or the level he would show someone to convince them. It works well over text, since he can send you a link.
What part of your job, your course or your sport is fascinating and never gets asked about?
Why ask it
People ask what he does and stop there. This asks for the odd inside detail: how the schedule gets made, what the referee says to the players, what happens to returned stock. He will probably start with 'well, this is boring, but', and it rarely is.
What's the best thing you've ever seen live: a game, a concert, anything?
Why ask it
A story about being there comes with the seats, the weather and who drove before it gets to the score or the set list. Find out what he kept from it, a ticket, a shirt, a blurry video, and which live thing is next on his list.
Opinions
What's your most unpopular opinion, the one you'll still argue for?
Why ask it
He chooses how serious this gets, and most guys begin with a band or a film that everyone loves and he does not. Argue back for fun if you disagree, and stop the moment it stops being fun.
What's the most overrated thing right now, and what deserves the attention instead?
Why ask it
A complaint with a recommendation built in, so the mood stays up. He might name a show, a restaurant, a player, a whole city. The 'instead' half is the one to follow, since that is him telling you what he loves.
Ghosts, aliens, luck: which do you believe in, even a little?
Why ask it
'Even a little' lets a skeptic admit to knocking on wood. If he believes in one, ask what convinced him, and there is nearly always a story about a house or a night. If he believes in none, ask what it would take.
Which conspiracy theory do you think is nonsense but love hearing about anyway?
Why ask it
Calling it nonsense up front keeps this light and away from politics. He gets to lay out the whole theory with enthusiasm and no risk of sounding like he buys it. If it starts heading somewhere tense, the moon landing is always there to change the subject.
Which decade had the best music, and can you make the case in three songs?
Why ask it
Three songs turn a shrug into a short playlist and a debate. It goes well in a car or over text, where he can send them. If his decade ended before he was born, ask who played it in the house when he was small.
Who's the greatest of all time at anything, where you think it isn't even close?
Why ask it
Sport is the usual territory, but drummers, chess players and chefs all count. Expect numbers. You do not need to know the field: 'who do people wrongly say instead' is enough to keep him going for ten minutes.
What's the best movie ever made, and is it also your favorite?
Why ask it
Many people give two different answers, and the gap is interesting. The 'best' is what he thinks he ought to admire and the favorite is what he loves. Which of the two he would put on tonight settles it.
Is a kind lie ever better than the truth?
Why ask it
Almost everyone says 'depends', so have a case ready: the bad haircut, the gift he will never use, the friend's terrible band. Where he draws the line shows how blunt he is likely to be with you.
How much money would be enough for you, as an actual number?
Why ask it
Asking for a number makes him work out what the money is for: a salary, a paid-off house, a boat. 'What would you stop doing the day you got there' is the follow-up. Money talk lands oddly on a first date, so keep this for someone you already know.
A job you love that pays badly or one you can stand that pays well: which is the better deal?
Why ask it
A real disagreement between sensible people, so it holds up at a dinner table or on a long drive. A teenager answers on principle and someone with rent answers from experience. Ask whether anyone he knows has made the trade and how it went.
What's the smallest hill you're willing to die on?
Why ask it
This is where you hear about the correct way to load a dishwasher or why a certain sequel should not exist. Take the opposite side whether you believe it or not. The more seriously he defends it, the better the conversation.
What should everybody have to do at least once?
Why ask it
Wait tables, travel alone, lose badly at something, sleep outdoors. The answer is nearly always something he did that changed him a bit, so the follow-up is simply 'when did you do it?'
City, suburb or middle of nowhere: where's the best place to grow up?
Why ask it
He will defend where he grew up or argue against it, and either way you hear what his childhood was like without asking directly. Ask where he would raise a kid only if you know him well. For anyone newer, 'where would you live now' is plenty.
Would life be better or worse if phones had never gotten smart?
Why ask it
Good for a guy who likes to think out loud. Push past 'both' by asking what he would miss in the first week and what he would be glad to lose. His own screen habits will come up without your having to ask.
No plan at all or every hour booked: which makes the better trip?
Why ask it
A travel opinion that is really about how he likes to live. Ask for the trip that proved his side. Worth knowing before the two of you go anywhere together, even for a day.
What if
If you could travel in time exactly once, would you go back or forward, and how far?
Why ask it
Back is usually to see something or fix something, and forward is curiosity about how things turn out. Either is a clue to what he thinks about. Ask whether he would be allowed to change anything, and let him set the rules.
Flying or invisibility, and what's the first thing you'd do with it?
Why ask it
The superpower question at its sharpest, because a choice of two gets an instant answer. The first use is the entertaining part. Anyone who picks invisibility then has to defend the plan that came with it.
Which three people, living or dead, would you put around one dinner table?
Why ask it
Asking for three instead of one makes him think about the mix: who would get along, who would argue. If a grandparent or someone he has lost is on the list, ask what he would want to hear from them and keep the rest for later.
If you won the lottery, what's the one thing about your life you wouldn't change?
Why ask it
The usual lottery answers are a car and a beach. Asking what stays put gets you what he already likes about his life: a Sunday game with the same guys, his street, his dog. If he says nothing would stay, ask what goes first.
If tomorrow could go exactly the way you wanted, what happens from breakfast on?
Why ask it
The perfect-day question, pinned to tomorrow so that he plans it with the people and places he really has. Notice how much of the day is spent alone and how much with company, and whether the plan is busy or mostly a couch. Any part of it you could arrange is worth remembering.
If you had to cross one thing off your bucket list before the year is out, which would it be?
Why ask it
A bucket list is easy to recite and never act on, so the deadline makes him choose the one he could really do: the race, the license, the trip to watch a team play at home. 'What's stopping you' is fair to ask once. If it is something two people can do, offer to come.
If every job paid the same, what would you do all day?
Why ask it
Pay drops out, so does status, and what remains is what he likes doing: coaching, fixing engines, cooking, being outdoors. The gap between this and his current plan is worth a gentle question, not a lecture.
If you were stuck on an island for a year, which album, which film and which person would you bring?
Why ask it
Three small decisions, each one arguable. The person is the telling one: note whether he goes for someone useful or someone he would not get sick of. Do not sulk if it is not you, since his best friend can build a fire.
If you could wake up tomorrow brilliant at one thing, what would you pick?
Why ask it
Instant skill, no practice: guitar, a language, a martial art, cooking, talking to anyone. How he would use it in week one tells you whether he wants the skill or the applause.
If you could live inside any movie, show or game for a month, which world are you choosing?
Why ask it
He will pick somewhere he has thought about more than he would admit. Ask what his job would be there. Someone who has read or played the thing will have a detailed answer, and you get to tease him for choosing a world with dragons.
If you could swap lives with anyone for one week, who would it be?
Why ask it
A week is short enough that he can choose out of curiosity instead of envy: an astronaut, a touring musician, his own dog. The follow-up is what he is hoping to find out. If he names someone he knows, that is more interesting than any celebrity.
If you had to move to another country next month, where would you start over?
Why ask it
'Had to' takes away the dreaming and makes him practical: the language, the weather, what he would do for work. Ask what he would miss within a week. That answer is a short list of what holds his life together.
When the world ends, who from your real life is on your team and what's each one's job?
Why ask it
The apocalypse question, made personal. He will assign roles with total seriousness: the cousin who can fix engines, the friend who would be no help but good for morale. Ask what your job would be, and brace for it.
If you could have the true explanation of one unsolved mystery, which would you pick?
Why ask it
A vanished plane, a lost city, what his dog is thinking. You learn what kind of curiosity he has, the documentary kind or the everyday kind. Get his own theory before you move on.
If you could pass one law tomorrow, serious or petty, what would it be?
Why ask it
Offering 'petty' is the trick, since that is where the good ones are: a fine for reclining an airplane seat, a ban on reply-all. A serious answer is fine too. Hear it out without turning it into a debate, unless he clearly wants one.
If you could restart at ten years old knowing everything you know now, would you?
Why ask it
Sounds like an easy yes until he thinks about sitting through school again. The reasons on each side are the interesting part: what he would fix, and what he would be afraid of losing by changing it.
Would you want to be famous, and for what?
Why ask it
Plenty of guys want the achievement and not the attention, and saying so tells you something. Ask how famous: recognized at the grocery store, or known only to people in his field. A flat 'no' deserves a 'why not'.
Changed his mind
What have you changed your mind about in the last year or two?
Why ask it
Offer something small if he stalls: a band, a neighborhood, a sport he used to mock. A guy who can name one without squirming is usually easy to disagree with. Then ask what did it, a person or an experience.
What did you want to be when you were seven, and what changed the plan?
Why ask it
The job itself gets a laugh, whether it was astronaut, garbage truck driver or striker for one particular team. Stay on the second half: the plan may have ended with a math grade, a growth spurt that never came or a better idea, and some of it is often still alive in what he does on weekends.
What did you refuse to eat as a kid that you'd now order on purpose?
Why ask it
About as low-stakes as a change of heart gets, and nearly everyone has an answer. Mushrooms, olives, spicy anything. Ask who or what converted him, and whether anything from the old list is still banned.
What were you most confidently wrong about?
Why ask it
The word 'confidently' is what makes it a story: he bet on it, told people, maybe argued with a teacher. Laugh with him. If the telling comes easily, he can be wrong in front of you without it stinging.
What did you think was cool at fifteen that makes you wince now?
Why ask it
He will go for the clothes, a catchphrase, an old username or a haircut copied from a singer. 'Is there photographic evidence?' is the only follow-up you need. For a guy who is fifteen or close to it, change the age to eleven.
What advice did you ignore that turned out to be right?
Why ask it
He will know who gave it, and the telling usually includes an impression of them. Wear the helmet, do not lend that friend money, start the essay earlier. Did he ever admit it to the person?
Who did you look up to at twelve, and how do they look to you now?
Why ask it
At twelve it is an older cousin, a coach or a player whose poster was on the wall. Some of them hold up and some do not, and the way he tells it shows what he admires these days. If the person let him down badly he may keep it short, and that is his call.
What were you a huge fan of that you've lost all interest in, and what killed it?
Why ask it
The reason is the part worth hearing, and it may be one moment he can describe exactly: a trade, a bad final season, the album where the band changed. See whether he would come back if it got good again.
What do you enjoy now that your younger self would have called boring?
Why ask it
He will sound a little embarrassed and a little pleased to admit to early nights, long walks, cooking or watching the news. It shows you what he is growing into, which a list of his hobbies will not. Ask what the fifteen-year-old version of him would say about it.
What did you badly want a few years ago that you're glad you didn't get?
Why ask it
It takes some distance to answer, so give him time. He may land on a spot on a team, a job or a move, and if it is a relationship, let him say as much or as little as he likes and do not ask for names.
What did you believe about dating at fifteen that turned out to be nonsense?
Why ask it
Usually funny: rules from older brothers, advice from movies, a theory about waiting three days to text. It is a relaxed way to hear how he thinks about relationships now. With a friend, it is simply a good story.
What's the best thing anyone ever talked you out of?
Why ask it
You find out whose opinion can stop him, and what he looks like with a bad idea: the tattoo, the purchase, quitting a week before it got good. He was probably not grateful at the time, so ask when that changed.
People
Who's the most interesting person you've ever met?
Why ask it
It could be a famous name, but more often it is a neighbor, an old boss or a stranger on a long bus ride. Ask what made them interesting, because his answer is his definition of the word. Then you know what he hopes to find in people.
What's the first thing you notice about someone, and what do you think people notice about you?
Why ask it
The first half gets a quick answer: shoes, a handshake, whether they look up from their phone. The second half slows him down, and it is the one to wait for. Tell him what you noticed first, as long as it is something kind.
What do the people you like most have in common?
Why ask it
He may never have thought about it, so expect a pause and then something specific: they are all a bit sarcastic, they all show up on time. On a date, you are allowed to check yourself against the list quietly.
Who's the funniest person you know, and what's their best line?
Why ask it
The line will not be as funny secondhand, and that is fine. Watching him try to tell it is the point. You hear what makes him laugh, and you get a name to ask about later.
Which friend would you put in charge in an emergency, and which one would you keep well away from the plan?
Why ask it
He will answer both halves at once, with real affection for the second friend. Ask for the incident that settled it. This is a quick way to learn his friends' names and roles before you meet them.
Which famous person do you think would be a good friend in real life?
Why ask it
Not the one he admires most, which is a different list. He is describing what he wants from a friend: someone funny, someone low-key, someone who would help him move. Ask who he thinks would be exhausting.
What's the best thing a stranger has ever done for you?
Why ask it
The story is usually short: a tow out of a ditch, a fare paid when his card failed, twenty minutes of someone's day spent on directions. So ask whether he has passed it on. Often he has, and would not mention it unasked.
What do other people do in public that drives you up the wall?
Why ask it
The pet peeve question, pointed at strangers so that nobody at the table is the target. Loud phone calls, stopping at the top of an escalator, walking slowly three across. Notice whether he rants or laughs, since that is how he handles being irritated.
Where's the line between confident and cocky?
Why ask it
Guys tend to have thought about this, having been on both sides of it. Have him name someone who gets it right. A person he knows is a better answer than a celebrity, because he can tell you what they do.
Do people really change, or do they just get better at hiding it?
Why ask it
He will answer from one case, usually someone close. Ask who he is thinking of, and accept 'someone I know' if that is all he offers. It is a big opinion inside a small question, so keep it for when the talk is already going well.
Who in your family are you most like, and do you take that as a compliment?
Why ask it
The second half gets the laugh and the real answer. 'My dad, unfortunately' said with a grin is different from the same words said flat. The shared habit, a laugh, a temper, a way of telling a story too slowly, is what to go after next.
What can someone do that earns your respect right away?
Why ask it
Whatever he lists is what he is trying to be himself, whether that is owning up to a mistake, being decent to a waiter or staying calm when a plan collapses. 'Who did you last see do it' turns the principle into a person.
Which fictional character is most like you, and which one would your friends pick?
Why ask it
Two answers, and the distance between them is the fun. He says the quiet hero and admits his friends would say the comic relief. If you have met his friends, say which side you would vote with.
Are you the same person with every group you hang out with, or does it shift?
Why ask it
Most people shift and few have said so out loud. Ask which group gets the version closest to the real one. If you are dating him or close to him, you will recognize some of this, and can tell him which version you get.
What do people assume about guys that you think is mostly wrong?
Why ask it
It asks him to speak for himself against a stereotype: that guys do not notice things, do not want to talk, only care about sports. Listen without correcting him, and ask which one gets pinned on him most.
How to ask so you get a story back
Practical guidance for the conversation itself
Choosing the question
Ask for a story or an opinion
A question is interesting when its answer cannot be one word. 'Do you like your job' gets 'it's fine'. 'What's the worst job you've ever had' gets a manager, a uniform and a Saturday that went wrong. Every question here is built that way, so if you change the wording, keep the part that asks for one particular time, person or reason.
Take the groups in order
Stories and Obsessions ask about things he already knows and likes telling, so they work with someone you met an hour ago. Opinions and What if need a little ease between you, because half the fun is disagreeing. Changed his mind and People ask him to think about himself, and go best once he has been talking for a while.
Choose for him, not from the top
Scan a group and pick the one you are curious about for this particular guy. If he has mentioned a team, a game or a job, go where that is. A question you want the answer to sounds different from one you are reading out, and he can tell.
One, then stay with it
A single question that runs for twenty minutes beats ten that get a sentence each. Do not reach for the next one while he is still warming up to this one.
Getting past the first short answer
Ask for the scene
The first answer is often a label: 'a road trip', 'my uncle', 'probably Italy'. Ask where he was standing, who else was there or what happened right before, and the label opens into the story. The note under each question suggests a follow-up for exactly this.
Guess, and be wrong
If he says he does not know, make a guess for him: 'I bet it's something to do with cars.' Correcting you is easier than starting from nothing, and the true answer often arrives inside the correction.
Make it smaller
'I don't know' is often about the size of the question. Shrink it: the best meal this year instead of ever, a rabbit hole from this week, an opinion about one team. Once he has answered the small one, the big one is easier.
Give your own answer
Answer the question yourself, briefly, and hand it back. It shows him how long an answer you are hoping for and keeps things even, so he is not the only one on the spot. Keep yours shorter than you hope his will be.
Know when to drop it
Tired, hungry or halfway through a game, nobody tells a good story. Two short answers in a row is your sign to talk about something else and try again another day. One flat conversation says nothing about him.
A date, a boyfriend, a new friend
A first or second date
Stay in Stories, Obsessions and What if. They let him be good company without having to explain his life, and they give you things to do next: the movie he has seen eleven times, the place he keeps wanting to go back to. Leave anything about past relationships until he brings one up.
A boyfriend you know well
You have heard his stories, so go to Changed his mind and People, or to the opinions you have never thought to ask about. The aim is an answer you could not have predicted. Guess out loud before he speaks and see how close you were.
A new friend, a classmate, a coworker
Obsessions and Opinions are the safest, because none of them reads as flirting. Ask in passing, while you are both doing something else. A running argument about something that does not matter is a fine thing to build a friendship on.
With other people around
Opinions and What if work at a table, since everyone can weigh in. Save the questions about advice he ignored, what he is glad he never got and what he is like with different groups for when it is the two of you.
Asking over text
Pick the ones that fit in a message
Either-or opinions, what-ifs and anything he can answer with a link, a song or a photo do well typed. Long stories do not: he will shorten them to a line, and you will have spent a good question. Keep those to ask out loud.
One question per message
Send it alone, without three more stacked beneath it and without 'random question but' in front. When he answers, react to his reply first and send your own answer second.
Ask for the evidence
Text has one advantage over talking: he can send the song, the photo of the thing he built, the clip of the play he says was the greatest ever. Ask for it. Then watch or listen before you reply, because he will know if you did not.
Bring it up in person
The best use of a text answer is as the start of the next conversation face to face. 'You never finished telling me about that job' shows you were paying attention, and gets you the long version.