Personal Questions to Ask a Guy
Personal questions to ask a guy who answers everything with a joke or a shrug, when you want to know him and not only his favorite pizza. The 100 questions are about his own life and feelings, in six groups ordered by how well you need to know him: Everyday, Family, Friends and love, Feelings, Beliefs, and Once he trusts you. The note under each one says how to ask it so it does not feel like an interview, what a joke in place of an answer usually means, or when to leave it.
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The questions
Each question, and why to ask it
Everyday
What's something about you that takes people a long time to find out?
Why ask it
He decides how big the answer is, which is why this works as the first personal question you ask. If he goes for a joke ('that I'm secretly a genius'), laugh, then ask for the second thing, the true one.
What does a really good day look like for you, from waking up to going to bed?
Why ask it
Say 'walk me through it' and let him narrate, since describing a day is easier than describing himself. Notice who is in it: a best day spent alone in a garage and a best day at a crowded table belong to two different people.
What's been taking up the most room in your head lately?
Why ask it
A softer way of asking what is on his mind, and he can answer with a car repair or a big decision. Ask it while you are both doing something else. If he says 'nothing much', take that at face value and try again next week.
What small thing gets on your nerves far more than it should?
Why ask it
Complaining is the easiest personal thing to hand over, so this lands even when he is in a joking mood. Under the rant there is usually something he cares about, like his time, his space or being listened to.
How do you wind down when the day has gone badly?
Why ask it
He might say a run, three hours of a game, a long drive or total silence. Whatever it is, remember it: the next time he disappears into that thing, he is probably having a bad day and it is not about you.
What's the most embarrassing thing that's happened to you that you can laugh about now?
Why ask it
'That you can laugh about now' keeps it on the safe shelf, so he will tell it as a story. Tell one of your own straight after. Trading embarrassments early is what makes harder questions possible later.
What's your guilty pleasure: the show, song or snack you'd deny in front of your friends?
Why ask it
Small stakes, and still a secret, so it is good practice for telling you things. Whatever he admits to, do not repeat it to his friends, even as a joke. He is finding out whether things are safe with you.
What do you own that you'd go back into the house for?
Why ask it
It is rarely the expensive thing. A watch from a grandfather, a worn-out hoodie, a box of old tickets: ask where it came from and you get a person and a story along with the object.
What do you like doing on your own that you wouldn't want company for?
Why ask it
The answer is where he goes to think, whether that is fishing, a long drive, the gym or cooking with music on. Those are also the hours not to take personally when he wants them to himself.
What habit are you trying to break, and how's it going?
Why ask it
'How's it going' lets him answer with a grin and 'badly', which is easier than a confession. Resist turning into his coach afterward. If he wants help he will say so, and reminders he did not ask for sound like nagging.
What are you proudest of from the last year or so?
Why ask it
A year is short enough that he does not have to rank his whole life. Guys who joke about everything often get quieter on this one. Let him be quiet, and when he answers say 'that's a big deal' before you move on.
What's one thing about yourself you'd keep exactly as it is?
Why ask it
A kinder way of asking what he likes about himself, which few people can answer on the spot without feeling they are bragging. He may start somewhere safe, like his hair or his memory for scores. Ask for one about the kind of person he is, and remember it: a compliment on that exact thing is one he will believe.
What do your friends give you a hard time about, and is any of it getting old?
Why ask it
The first half is funny and the second half is the personal question. If he says it is all fine, believe him for now. If he pauses before he says it, you have found something to leave out of your own jokes.
What do you wish you had more time for?
Why ask it
The answer is what he would be doing if school, work and everyone's expectations got out of the way. Ask what is eating the time instead. It is a gentle route to how he feels about his job or his classes.
What do you think people notice first about you, and what do you wish they noticed?
Why ask it
First you hear how he thinks he comes across: tall, quiet, loud, funny. The wish is the personal part, and a guy who is known as the funny one will often say he would like to be taken seriously now and then.
What's the last thing that made you really happy, not just fine?
Why ask it
'Not just fine' asks him to tell the difference, which is a small step toward talking about feelings at all. If it takes him a while, that is not a bad sign. Plenty of people do not keep track.
Are you more of a talker or a listener when it's only two people?
Why ask it
A question about the very thing you are doing, so it can clear the air. If he says listener, he has just told you why your questions get short answers, and that he may open up more when you talk first.
Family
How close are you to your family these days?
Why ask it
'These days' admits that it changes, so he can say 'closer than I was' or 'it's complicated' without explaining. If you get one flat word, move to something easier about where he grew up and leave the reason for another time.
Where did you grow up, and what was it like being a kid there?
Why ask it
Easy to ask anyone, and it opens the whole subject of childhood through streets, weather and what there was to do. If he moved around a lot, ask which place he calls home when someone asks. That choice is personal in itself.
If you could be a kid again for one day, which day would you pick?
Why ask it
This is the favorite-childhood-memory question with a choice built in, so he has to settle on one day and say why. Listen for who is in it and what he was allowed to do. If nothing comes to mind, switch to what he got in trouble for, which nearly everyone can answer.
What were you like at fourteen, and would the two of us have been friends?
Why ask it
The second half keeps it playful and lets him tease you back. Listen to how he talks about that kid, with a wince, with affection or as a stranger, because it is how he feels about where he started.
What did you get in trouble for most as a kid?
Why ask it
He will enjoy telling this one: talking in class, fighting with a brother, taking things apart, coming home late. Then ask how the adults dealt with it, because that half is often more personal than the crime.
If you had to sum up your childhood in one word, what's the word, and why?
Why ask it
One word is a small ask, and the 'why' is where he decides how much to tell you. 'Loud' and 'quiet' are both whole stories. A joke word like 'sticky' is fine too: laugh and ask what the serious word would be.
How would you describe your mom to someone who's never met her?
Why ask it
Describing her to a stranger is easier than saying how he feels about her, and the feeling comes through anyway in what he picks. If someone else raised him, he will tell you here, so follow his wording from then on.
What's your dad like, and how much of him do you see in yourself?
Why ask it
For a lot of guys this is the most loaded family question there is, so ask it only after easier ones have gone well. Not everyone has a dad in the picture. If the answer is short or sharp, say 'fair enough' and do not come back to it that day.
Who in your family are you most like, whether you like it or not?
Why ask it
Usually he knows at once, and the tail of the question lets him groan about it. The follow-up is 'which part': the temper, the stubbornness, the sense of humor. That is him describing himself with someone else's name on it.
What would your brother or sister tell me about you that you never would?
Why ask it
Playful, and it gets you the family's version of him: the bossy one, the kid who cried at cartoons, the one who talked to the dog. Notice whether he tells it fondly or with a small flinch. With an only child, make it a cousin or the friend who has known him longest.
Who looked out for you when you were a kid?
Why ask it
It could be a parent, an older sister, a grandmother, a neighbor or a coach, and the name he gives is often someone he still measures himself against. If the answer is 'I looked out for myself', leave it there until a day when he brings it up.
What do you remember best about your grandparents?
Why ask it
He may give you a smell, a phrase or a chair nobody else was allowed in. Guys who will not talk about feelings will often talk warmly about a grandparent, so this is a good one for a guarded day. If he never knew them, ask who filled that spot.
What family tradition would you keep going if it were up to you?
Why ask it
Sunday dinners, a fishing trip, the same bad movie every December. He is telling you what home felt like at its best. Having no traditions is an answer too, and he may tell you what he would start.
What was school like for you: good years, bad years, or just years?
Why ask it
The three choices let him answer without a speech. If it was bad years, ask what would have helped, not what went wrong. If he is still in school, ask which year so far he would not repeat.
Are you the same guy with your family as you are with your friends?
Why ask it
Nearly everyone says no, and the difference is the interesting part: quieter at home, funnier with friends, more careful around one parent. Ask which version is closer to the real one and let him think about it.
Did the men in your family talk about how they felt, or was that not done?
Why ask it
This often explains the joke and the shrug better than anything he could say about himself. Ask it with curiosity, never as a diagnosis. If he says 'not done', you can tell him he is already doing better than that by answering.
What did your parents get right?
Why ask it
Asking for what went right is safer than asking for what went wrong, and he will often tell you both anyway. If he struggles to name anything, do not fill the silence with guesses. Let him get there or change the subject himself.
What do you wish your family understood about you?
Why ask it
It can be small (that he is not lazy, that the music is not a phase) or it can be the center of him. Do not offer to explain him to them, and do not take sides against his family: he can criticize them and you cannot.
Friends and love
Who knows you best, and what did it take for them to get there?
Why ask it
The second half is the real question, because the answer is a recipe: years, a hard time shared, a person who simply kept asking. It tells you what it takes to get close to him.
Do you and your friends ever talk about real things, or is it mostly jokes?
Why ask it
Ask it lightly, because plenty of guys have friendships that run on jokes and are proud of them. If it is all jokes, you may be the only person he practices this kind of talk with, which is a reason to go slowly.
What kind of friend are you when someone's having a hard time?
Why ask it
Some guys show up with food, some fix the thing, some sit there, say nothing useful and stay anyway. However he helps other people is usually how he would like to be helped, so file it away.
What's the nicest thing a friend has ever done for you?
Why ask it
He gets to talk about being cared for without having to use the word. Whether it was a drive across town at midnight or a loan nobody mentioned again, the story shows you what counts as love in his book.
Do you make new friends easily, or do you stick with the ones you've got?
Why ask it
Neither answer is better. A guy with the same four friends since school lets people in slowly and keeps them, so you are being told how long this might take and that it tends to last.
Is there a friend you fell out with that you'd like to put things right with?
Why ask it
If there is, he will go quiet for a second before he answers. Ask what he would say if he ran into them, and stop short of telling him to send the message. That decision is his, and pushing makes him sorry he mentioned it.
Who was your first crush, and did they ever find out?
Why ask it
Sweet, and far enough back to be harmless. He will tell it as comedy, which is fine. If they never found out, ask what stopped him: a guy who said nothing at eleven may still be slow to say things now.
What draws you to a person that has nothing to do with looks?
Why ask it
Ruling out looks gets you past the easy answer. He will name something like being easy to talk to, being kind to waiters or being able to laugh at yourself. Resist fishing for whether it describes you. If it does, he will tell you.
What puts you off someone quickly, even if you liked them before?
Why ask it
These are his values stated backward: a guy who names rudeness to strangers or gossip is telling you what he expects of himself. If the answer is a dig at an ex, let it pass without asking for the story.
Do you know your love language, or what would you guess it is?
Why ask it
He may roll his eyes at the term, so offer plain choices: someone saying it, someone showing up, time, a hug, a small present. Then ask how he shows it himself. Guys who never say 'I care about you' are often saying it with a ride or a repair.
What was your first real relationship like, and how old were you?
Why ask it
Letting him decide what counts as 'real' is part of it. Keep your face friendly while he talks about someone else, or this is the last ex you will hear about. If he has never had one, ask what he imagines it being like and carry on.
How many times have you been in love, if you're counting honestly?
Why ask it
The number matters less than how he gets to it: who he includes, who he waves off as 'not really'. A joke number ('with pizza, daily') means he is not ready to say it out loud here. Smile and let it go.
Who was the hardest person to get over, and what finally helped?
Why ask it
This is the heartbreak question, asked so that he can give a name and a number of months and stop there. 'What finally helped' matters more than who it was: time, his friends, a move, deleting the photos. 'Nobody' may mean nobody or may mean not yet, and either is fine to leave.
How did your last relationship end, and how do you feel about it now?
Why ask it
Listen for how he talks about the other person more than for what happened. Someone who can say what he got wrong has thought about it, and someone who puts all of it on his ex may not have yet. Ask once, and leave the details alone.
What did your last relationship teach you about what you need?
Why ask it
Framed around him, so he does not have to run anyone down to answer. More space, more honesty, someone who says what is wrong instead of going silent. If you are dating him, hear it as information and not as a list of demands.
Are you still in touch with any of your exes?
Why ask it
Ask only if either answer is fine with you, because he will read your face. 'Yes, we're friendly' and 'no, never' are both ordinary. What you are learning is how he ends things, cleanly or with the door left open.
Has anyone ever broken your trust badly, and how long did it take to trust people again?
Why ask it
It may be an ex, a friend or a parent, and he does not owe you the name. The second half is the useful part: you hear whether he is still in that stretch. If he is, what he needs from you is patience and no speeches.
Feelings
What's your biggest fear, the real one and not spiders?
Why ask it
Naming the joke answer first takes it off the table, kindly. The real ones tend to be failing, being a disappointment, ending up alone or losing someone. Whichever he says, do not tell him it will never happen. 'That makes sense' is better.
What makes you angry faster than anything else?
Why ask it
Anger is often the easiest feeling for a guy to admit to, which makes this a good first question about feelings. Ask what he does with it next. Under 'being lied to' or 'being ignored' there is sometimes a hurt, and he may not be ready to call it that.
What's the last thing that made you tear up, even if you hid it?
Why ask it
'Even if you hid it' admits that he probably did, which makes it easier to own. If he says he cannot remember, he may truly not. Never tease him about the answer, then or later, or you will not get another like it.
When you say 'I'm fine', what's it usually covering?
Why ask it
Ask with a smile, because you are letting him know you have noticed. Tired, annoyed, worried about money, needing an hour alone: each one calls for something different from you. Next time he says 'I'm fine', you can ask 'which kind?'
When something's wrong, would you rather I ask, or wait until you bring it up?
Why ask it
The most practical question you can ask a quiet guy, and he can answer it without revealing a thing. Then do what he says. If he says wait, waiting is hard, but asking anyway teaches him that his answer did not count.
Do you find it hard to talk about how you feel, and where do you think that comes from?
Why ask it
For a guy who jokes and shrugs, this names the thing without blaming him for it. Many will say 'I just don't think about it much', and that can be true. If he has a theory, such as his dad, his friends or being laughed at once, listen and do not improve on it.
What do you lie awake thinking about?
Why ask it
Late-night thoughts are the ones he does not edit. Money, a parent's health, whether he picked the right path, something dumb he said years ago. If he says he sleeps like a log, laugh and ask what would keep him up if anything could.
What hurts your feelings that you'd never admit to in the moment?
Why ask it
It might be getting left out of a plan, a joke about his height or a parent comparing him to a brother. He is handing you a map of where not to step. Use it to be careful, and never as ammunition when you are arguing.
What's something you're insecure about that nobody would guess?
Why ask it
Hold back 'but you're great at that', which tells him you were not listening. Ask how long it has been there instead. Weeks later, unprompted, mention something you admire about exactly that.
Do you ever feel lonely even when there are people around?
Why ask it
A yes or no he can leave at one word. If it is yes, ask when it happens most: at parties, at home or with certain friends. Do not take it as a comment on you, since it has usually been there longer than you have.
Who expects the most from you, and is it ever too much?
Why ask it
The second half gives him permission to say it is heavy without sounding ungrateful to a parent, a coach or a boss. Sometimes the answer is himself. Either way he is not asking you to fix it, so skip the advice.
What makes you feel needed?
Why ask it
Plenty of guys feel cared about when they are useful: asked to fix, carry, drive, explain. If that is him, asking for his help now and then is a kindness and not a burden. If he says 'nothing really', ask when he last felt it.
What do you worry people think of you?
Why ask it
A joker often worries that people see only the jokes, or that he is boring once they stop. Whatever is on his list, tell him one true thing you think of him that is not on it.
What's a dream of yours that you think people would laugh at?
Why ask it
Whatever it is, do not laugh, and do not say 'you should totally do it' in the first breath either. Ask what the first step would be if it were not ridiculous. He will remember for a long time that you took it seriously.
When you picture yourself ten years from now, what's the part you most want to come true?
Why ask it
Ten years is far enough off that he can say it without defending a plan. Notice whether he starts with work, a place or the people around him. If he says he never thinks that far ahead, ask about next year: some people plan in months.
When do you feel most at peace?
Why ask it
Ask it after a heavy answer, because this one is calm: early mornings, driving at night, the minute after a game. Offer to do that thing with him sometime, or to stay out of it if it is something he does alone.
Beliefs
What are the three things that matter most to you, in order?
Why ask it
'In order' is what makes him think. Family, friends, work, faith, freedom, his team: the ranking is more personal than the list. Give yours afterward and compare without scoring.
Is there a rule you try to live by?
Why ask it
He may quote a coach, a grandfather or a movie, and may be a little embarrassed that he has one. Ask when it was last tested. A rule with a story attached is one he lives by and not one he read somewhere.
Who do you look up to, and have you ever told them?
Why ask it
You hear what kind of man he is trying to be, described as somebody else: an uncle who never raises his voice, a coach, an older brother. The second half usually gets a no and a laugh. Leave it at that unless he says he wishes he had.
What were you taught about how a man should act, and how much of it do you still believe?
Why ask it
Do not argue with the list, even where you disagree. 'Don't complain, handle it yourself' may be the reason he shrugs at your questions, and it is his to decide what he keeps. Ask who taught it to him.
Do you believe in God, or are you still working that out?
Why ask it
Ask because you want to know, with no answer you are hoping for. If faith matters a lot to one of you, sooner is better than later. A one-word reply usually means private, so say 'fair enough' and move on.
What makes someone a good person, in your book?
Why ask it
Watch whether he describes things people do or things they are. The follow-up is 'who do you know who is like that', and the person he names tells you what he is aiming at.
What's a line you won't cross, whoever is asking?
Why ask it
He may tell you about the time he was asked to lie for someone or turn on a friend. If it comes out as a joke ('pineapple on pizza'), he is telling you he would rather stay light today.
Would you rather be told a hard truth or be spared it?
Why ask it
Most people say truth, so follow with 'even about yourself?' His answer tells you how to bring up a problem with him later: straight out, or gently and with warning.
Do you forgive and forget, or forgive and remember?
Why ask it
A choice of two keeps it quick. 'Remember' is an honest answer and nothing to be alarmed by. Ask what somebody would need to do for him to drop it completely.
What do two people in a relationship owe each other?
Why ask it
Honesty, time, loyalty, telling the other one when something is wrong. If you are dating him, resist turning each item into 'so do we have that?' Let it stay a belief tonight. You can come back to it.
Do you believe in love at first sight, or does it take a while for you?
Why ask it
Lighter than it sounds, and a fair one to ask early. The second half is where he tells you his own pace. A guy who says it takes a while is asking, in a way, not to be hurried.
What's your honest opinion of marriage?
Why ask it
An opinion, not a proposal, and say so if he looks alarmed. It usually leads straight to his parents' marriage, which is where the opinion was formed. If they split up, let him set how much of that he tells.
How do you feel about having kids someday: yes, no, or ask me later?
Why ask it
'Ask me later' is on the menu so that a teenager or a guy who has not thought about it has an honest answer. Whatever he says, do not negotiate. With someone you are serious about, a firm no or a firm yes is worth knowing early.
What do you believe that most of your friends don't?
Why ask it
This is the opinion he keeps out of the group chat, whether it is about politics, faith or whether college is worth it. He is trusting you not to laugh, so ask how he came to it before you say what you think.
What do you think you're here to do, if anything?
Why ask it
'If anything' lets a skeptic answer too. Some guys have a clear answer (look after my family, build things) and many have never been asked. A long pause is a good sign, and 'no idea, you?' deserves a real answer from you.
Once he trusts you
Is there something you've never told anyone that you'd tell me?
Why ask it
The question everyone wants to ask first and should ask last. Keep it for a guy who already tells you things unprompted, and expect 'not tonight' as often as an answer. If he does tell you, it goes no further, whatever happens between you.
Why do you think you joke when things get serious?
Why ask it
It only works said with affection, by someone he trusts, at a calm moment. Asked during an argument, it is an accusation. He may say it is how his family did it, or that it keeps people comfortable. If he answers this with a joke too, laugh. He heard you.
What part of yourself do you hide from most people?
Why ask it
He might say the worrier, the nerd, the guy who cares too much what his dad thinks. Thank him for showing you. Then treat that part gently in front of others, because he will be watching what you do with it.
Which year of your life would you hand back if you could?
Why ask it
He can give you the year and nothing else, and that is a full answer. If he tells you why, listen without comparing it to a hard year of your own. Ask who knew at the time.
Has there been a time you weren't okay for a long while, and did anyone know?
Why ask it
Ask in private, with time to spare, and be ready for yes. You are not his counselor and you do not need to solve it: 'I'm glad you told me' is enough. If it sounds like it is still going on, encourage him to talk to a doctor, a counselor or an adult he trusts, and do not promise to keep that secret.
Who has hurt you the most, and do they know?
Why ask it
Whoever he names, a parent, an ex or a friend who vanished, say nothing against them, since he may still love them. 'Do they know' usually gets a no, and he is not asking you to change that.
Who do you miss that you can't see anymore?
Why ask it
It may be someone who died or someone who simply left his life. Ask what they were like and let him tell stories, which is nearly always easier than describing the missing. Skip it if he has had a recent loss, unless he raises it.
What's the biggest mistake you've made, and what did it cost you?
Why ask it
He is trusting you with the version of himself he likes least. Do not rush to excuse it and do not look shocked. Ask what he does differently now, which lets him end on who he has become.
Is there something you still feel ashamed of, even though you know better?
Why ask it
A yes can be the whole answer, and 'what is it' should never be asked twice. If what he tells you is something that was done to him, believe him, thank him for telling you and ask whether he has someone to talk to about it.
What would you say to one of your parents if you knew they'd really listen?
Why ask it
Sometimes it is thanks he has never managed to say, and sometimes it is something much harder. Do not suggest he go and say it. Hearing himself say it to you may be all he wanted.
What are you still waiting for an apology for?
Why ask it
This shows you what he has not put down. He may shrug and say it does not matter, and the shrug counts for less than the fact that he remembered at once. You cannot give him that apology. You can say you understand why he is still waiting.
Have you ever felt like you weren't enough for someone?
Why ask it
Ask who it was, a parent, an ex, a team, and how old he was. Reassurance tends to bounce off in the moment, so the kind thing is to listen and not argue with the feeling.
What's the thing you like least about yourself?
Why ask it
Ask it only if you can hear the answer without correcting it. 'My temper' or 'I give up too easily' is him being honest, and 'no you don't' closes the door. Ask whether it is getting better or worse, and leave it there.
What are you afraid I'd think if I knew everything about you?
Why ask it
For a boyfriend or a very close friend, late in a long talk. He may not answer, and asking still tells him you expect to stay. If he does, the only good reply is that you are still here.
Is there anything you need from me that you find hard to ask for?
Why ask it
For a boyfriend or a close friend, and he may want a day to think about it. The answer tends to be small and practical: more warning before plans change, less teasing in front of his friends, an hour to himself after work. Whatever he asks for, try it before you discuss it.
Do you feel like you can be yourself with me, and when can't you?
Why ask it
Brace for the second half, because a useful answer may sting: when your friends are around, when you ask too many questions, when he thinks you are disappointed. Say thank you first. Defend yourself later, if you still want to.
What was it like telling me all of this?
Why ask it
For the end of any talk where he told you something hard. 'Weird' and 'kind of good' are both normal. It lets him say if it was too much, and it tells him that how he feels about talking matters as much as what he said.
How to ask a guy personal questions without it feeling like an interview
Practical guidance for the conversation itself
Asking so it feels like talking
Trade, do not collect
Answer every question you ask, and on the harder ones answer first. A guy who hears three questions in a row with nothing coming back starts to feel examined. Keep your own answer about the size you are hoping for from him: a few honest sentences, not a speech.
Ask while you are both doing something
Driving, cooking, walking the dog, waiting for food, playing a game on the couch. With his eyes on something else, a personal question sounds like a passing thought, and he can take his time without a silence to fill. Sitting him down for 'a talk' is what produces the shrug.
Ask what happened before you ask how it felt
'What did you do when you found out?' gets a story. 'How did that make you feel?' gets 'fine'. Many of the questions here are built the first way on purpose. Once he has told the story, the feeling is usually in it, and you can say it back to him: 'that sounds like it was scary'.
One question, then follow his answer
The list is somewhere to pick one question from, not a script. Ask it, then let your next three questions come from what he said. If you never get to a second question from the page, the first one worked.
Keep the page out of sight
Do not read these off your phone across a table. Pick two beforehand, remember them roughly and put them in your own words. A question that sounds like you gets a more honest answer than one that sounds like a quiz.
When he answers with a joke or a shrug
The joke with the answer inside it
Listen to what the joke is about. A guy who answers the biggest-fear question with 'dying alone surrounded by cats, obviously' has told you something and wrapped it so that he can deny it. Laugh, and take the inside seriously without unwrapping it in front of him.
The joke that closes the subject
This one is quicker and flatter, and a change of topic comes right behind it. It means not now, or not here. Go with the new topic. 'No, seriously' turns a question into pressure, and he will remember the pressure longer than the question.
The shrug and 'I don't know'
A shrug usually means the question was too big to answer on the spot. Make it smaller: 'this month' in place of 'ever', or 'what would your brother say?' in place of 'what do you think?'. If the smaller one gets a shrug too, give your own answer and move on. He has heard the question, and it sometimes comes back from him days later without your asking again.
When he turns it back on you
'I don't know, what's yours?' is not a dodge. He wants to see what an answer looks like and whether it is safe to give one. Answer properly. He will often follow with his own before you have finished.
When the jokes never stop
If the lighter groups get real answers and only the hard ones get jokes, nothing is wrong: that is where he is, and the order of this page is built for it. If even the Everyday questions still get punchlines after months, say so once, on a calm day: 'I like the jokes, and I would like to know you too.' Then see what he does with it. If nothing changes, a longer list of questions will not help, and what you do next is yours to decide.
Which group for which guy
A guy you have just started talking to
Everyday, and the lighter half of Family: where he grew up, what he was like at fourteen, what he got in trouble for. In Friends and love, the first-crush question and the two about what draws him to someone and what puts him off are fine once you are both laughing. Leave his last relationship alone until he mentions it himself.
A guy you are dating
Friends and love and the first half of Feelings suit this stage. Ask about exes only as much as you would want to be asked. Beliefs is fair once you have been seeing each other for a few weeks, and the questions about marriage and kids ask for his opinions, not for a promise.
Your boyfriend
The practical ones pay off most: whether he wants you to ask or wait when something is wrong, what 'I'm fine' covers, what he needs from you and finds hard to ask for. Ask them on an ordinary good day. Once he trusts you is for him as well, but as a few questions a year and never an evening's worth.
A friend or a brother
The same order holds. Skip the questions about the two of you as a couple and lean on Family, Feelings and Beliefs, ideally in a car. With a brother you already know the family answers, so ask the ones where his version might differ from yours.
Over text
Everyday and the either-or questions in Beliefs travel well by message, and some guys will type what they would never say. Keep Feelings and Once he trusts you for when you are together, or at least on a call. Never screenshot an answer for your friends.
When to leave it, and what to do with what he tells you
Signs he is done for today
Answers getting shorter, a look at his phone, a stretch, a joke after a run of real answers. Stop one question before he wants you to. Ending while it still feels good is what gets you another conversation.
Say thank you, not 'and?'
When he tells you something that cost him, keep the reply short: 'thanks for telling me' or 'I didn't know that'. A follow-up question straight away can feel as if the answer was not enough. Leave a pause and see whether he adds to it on his own.
Do not fix, argue or diagnose
He told you how it is for him. He did not ask for a plan, a counterargument or a theory about his childhood. If you have advice, ask whether he wants it first, and accept a no.
What he tells you stays with you
Not to your friends, not to his, not to his mother, and never thrown back at him in an argument. One answer repeated or used against him can end this kind of talk between you. That holds after a breakup too.
If it is more than you can carry
Now and then a personal question brings up something serious: trouble at home, a very low stretch, something that was done to him. You can care about him without being the only one who knows. Encourage him to talk to a counselor, a doctor or an adult he trusts, and if you think he is in danger, tell an adult yourself even if he asked you not to.