Questions to Ask a Guy to Get to Know Him
Questions to ask a guy to get to know him, for the stage after hello: a guy you like, one you just met, or one you have been texting and want to know past his profile. The 96 questions start with what he can answer without thinking and end with ones that need some trust, in six groups: Everyday life, Favorites, Family and friends, What he is like, Hopes and plans, and Deeper. The note under each one says what to listen for in his answer and what to tell him about yourself in return, and everything here is about who he is, not what he wants from you.
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The questions
Each question, and why to ask it
Everyday life
Where's home for you: here, or somewhere you'd have to show me on a map?
Why ask it
He gets to decide whether home is the town he was raised in or the place he sleeps now, and a guy who names the first while living in the second is often a little homesick. Answer with yours and one thing only a local would know about it, like the best bad pizza or the hill everyone learned to drive on.
What keeps you busy during the week: school, work or a bit of both?
Why ask it
Asking it this way saves you from guessing his situation and getting it wrong. Listen past the job title or the class list for the one part he talks about longest, and ask about that part next.
What's your idea of a weekend well spent?
Why ask it
'Well spent' gets you the weekend he would choose, not the one he usually has. Listen for whether it is crowded, built around one hobby or mostly sleep, then describe your own so he can hear where the two would overlap.
What are your hobbies, including the ones you'd be slightly embarrassed to list?
Why ask it
The second half is where the good answers are: the model trains, the fantasy league spreadsheet, the bread. Trade one of your own embarrassing ones straight away so he is not out there alone.
Dogs, cats, both or neither?
Why ask it
Four possible answers and every one starts a conversation, usually about a specific animal with a specific name. Ask to see a photo. A guy with forty pictures of his dog ready will be happy for the next ten minutes.
Who do you know here, or did somebody drag you along?
Why ask it
This is for a guy you met ten minutes ago at a party, a game or a friend's house, and it is no use over text. Whoever he names, ask how the two of them met. You learn how long he keeps his friends, and the 'dragged along' half lets him admit he did not want to come either.
Are you a morning person, or is it safer not to talk to you before ten?
Why ask it
He can admit to being a bear before noon because you have already made the joke for him. It also tells you when to text: a cheerful message at seven lands very differently on a guy who is at the gym by then and one who is face down until ten.
Do you live with family, with roommates or on your own?
Why ask it
A plain fact that explains a lot about his week: who he eats with, how much say he has over his evenings, whether there is a little brother listening at the door. If he lives at home, ask who else is in the house, not when he plans to leave.
What do you do with the first half hour after you get home?
Why ask it
You are asking how he resets. Some guys go straight to the fridge, some put on a game for an hour, some run before they can talk themselves out of it, and the answer tells you whether he wants quiet first or company right away.
Do you play a sport or work out, or is that more of a plan than a habit?
Why ask it
The joke at the end lets him be honest instead of inventing a gym routine. If he does play, ask what position or what he is training for, since guys who love a sport can explain their role in it for a long time.
What app do you open without even deciding to?
Why ask it
He can answer in one word, and the word is where his attention drifts when nothing is asking for it: chess, a scores app, a map of the flights overhead. Have your own ready, because he will turn the question around, and 'the weather, for no reason' is a perfectly good answer.
What's your favorite part of an ordinary day?
Why ask it
Not the highlight of his year, the highlight of a Tuesday: the drive home with the music up, practice, the first quiet half hour. Small answers like these are the ones you can join in on later.
How did you get into the work or the subject you're doing now?
Why ask it
There is often one teacher, one uncle or one summer job behind it, and that story beats the job description. Listen for whether he sounds like he chose it or is still deciding, and do not push if it is the second.
What are you in the middle of right now: a season, a project, exams, a move?
Why ask it
Whatever is eating his weeks, knowing it early keeps you from reading a slow reply as a lack of interest, and it gives you something to ask about next week: 'How did it go?'
What's worth spending good money on, in your opinion?
Why ask it
What he will pay full price for is a shortcut to what he values, whether that is concert tickets, good shoes, parts for the car or a decent mattress. It is also a friendlier way in than asking what he does with his paycheck.
What's something you do every week no matter what?
Why ask it
Sunday dinner at his grandmother's, pickup basketball, a call to his brother. A standing commitment shows what he protects when life gets busy. If he cannot think of one, ask what he wishes he had time for every week.
Favorites
What kind of music do you like, and who would you pay to see live?
Why ask it
A genre is small talk, but the artist he would buy a ticket for is a real answer. If you know them, name your favorite song. If you do not, ask where to start and listen before you next talk, because coming back with an opinion is hard to beat.
What's your fallback movie, the one that wins when nobody can agree on anything else?
Why ask it
The fallback is more honest than the official favorite. It is often something from when he was about twelve, so ask who he first watched it with, then name yours and see whether he approves.
What's the last show you finished faster than you meant to?
Why ask it
A season gone in one weekend is a strong review. If you have seen it too, you have an hour of conversation ready. If not, let him pitch it to you in three sentences and see how he sells.
If you could only eat one cuisine for a year, which one are you picking?
Why ask it
More fun than asking for a favorite food because it forces a trade-off, and he will argue his case. File the answer away: it tells you where to suggest eating, and what never to suggest.
What's your order at a coffee shop, or are you not a coffee person at all?
Why ask it
Black coffee, something with four modifications, hot chocolate, 'just water'. It is a tiny thing to know about someone, and remembering it the next time you are in a line together lands better than a big gesture.
Sweet or salty, and what's the snack you can't be trusted around?
Why ask it
Two seconds for the first half, then a confession. Plenty of people have one item they cannot keep in the house, and he will name the brand. Admit yours, and you both know what to bring to a movie.
How spicy can you go before you regret it?
Why ask it
Save it for when the food arrives. He will either brag or admit that mild is his limit, and both are endearing. It also settles who gets to order for the table.
Do you play video games, and what's your game right now?
Why ask it
If the answer is yes, ask what he likes about that particular game: the competition, the story, or the friends he plays with. You do not have to play to follow along, and letting him explain it badly at first is part of the fun.
What's the best game, match or race you've ever watched?
Why ask it
A fan will have this ready, with the score and where he was sitting. Someone who does not follow sports can answer with a school final or a video game tournament, so nobody is left out. Listen for who he watched it with.
Beach, mountains or a big city: where would you spend a week off?
Why ask it
Three choices make it quick, and the reason is the part worth hearing: rest, something to climb, or twelve places to eat within a block. Pick one yourself and you will both find out early whether a shared trip would be easy or a negotiation.
Where's the farthest you've ever been from home?
Why ask it
Works for the guy who has backpacked across a continent and the one whose answer is a school trip three states over. Ask what surprised him there. If the answer is short, ask where he would go first.
What's something you keep recommending to people: a podcast, a book, a channel?
Why ask it
Whatever a person keeps recommending is a small self-portrait, since it is the thing he is happy to be linked with. Try it, even one episode or one chapter. Telling him what you thought is a ready-made reason to talk again.
What's a movie or show everyone loves that you just don't get?
Why ask it
A harmless disagreement is one of the faster ways to feel comfortable with someone. Let him make his case, defend the thing if you love it, and notice whether he can argue without needing to win.
What cartoon, game or toy was basically your whole childhood?
Why ask it
Nostalgia is safe ground, and you will see his face change when he names it. If you grew up on the same thing, you will both be quoting it within a minute. If he is still a teenager, it works just as well about age eight.
What song do you know every single word to?
Why ask it
The song he knows by heart is often not the one he would call his favorite: a cartoon theme, something his mom played on every car ride, a hit from the year he turned thirteen. He will ask for yours, so decide in advance whether you are willing to prove it.
What's a gift you still have years after you got it?
Why ask it
The one he kept is hardly ever the most expensive. A watch from a grandfather, a letter, a jersey somebody remembered he wanted: you find out what a thoughtful gift means to him, and who in his life pays that kind of attention.
What would your perfect birthday look like?
Why ask it
Ask when it is while you are on the subject. A big party, a quiet dinner and pretending the day is not happening are three different ways of wanting to be celebrated, and if you are still talking when the date comes around you will know what to do and what to avoid.
Family and friends
Do you have siblings, and where do you fall: oldest, youngest or stuck in the middle?
Why ask it
He will have opinions about what his spot did to him, and an only child will have a few about that too. Say where you fall, since two oldest children comparing notes, or an oldest and a youngest arguing about who had it easier, can fill a whole lunch.
Who are your closest friends, and how would you sum up each one in a sentence?
Why ask it
One sentence each keeps it moving and makes him pick what matters about them. You will hear what he admires in people, and you will recognize the names when they come up later.
What kind of kid were you: the quiet one, the loud one or the one always in trouble?
Why ask it
The three options are only there to get him started, and plenty of guys pick a fourth. Ask for the story that proves it, like the note sent home or the tree he fell out of, and offer the one your own family still tells about you.
What did your family do for fun when you were growing up?
Why ask it
You hear what an ordinary good time looked like in his house: camping trips, card games, long drives to see relatives, every weekend at a ball field. It often explains the hobbies he has now, so ask which of those he would still sign up for.
What's the best day you remember from being a kid?
Why ask it
Give him a second with this one. The first thing that comes to mind is often a big trip, and the better answer tends to be small: a snow day, a grandfather's workbench, the summer the street flooded. Ask who else was there, because that person usually still matters to him.
Where do most of your friends come from: school, work, a team, somewhere else?
Why ask it
You learn which part of his life produces his people, and whether he has kept friends across more than one chapter. One tight group and a dozen loose circles are simply two different social lives, and it helps to know which you would be meeting.
Which of your friends is the funniest, and what's the proof?
Why ask it
He will answer fast and then have to back it up with a story, which is the real reason to ask. Pay attention to the kind of funny he admires: quick, absurd, quietly savage. It is often the kind he is trying to be.
What are the people who raised you like?
Why ask it
Worded so it fits a mom and dad, a single parent, grandparents or anyone else. Notice the tone as much as the facts: fond, careful, joking. If he keeps it brief, take the hint and move to an easier one.
What did dinner look like at your house growing up?
Why ask it
A dinner table is easier to describe than a family, and you learn much the same things: everyone seated at six, plates in front of the television, or whoever was home fending for themselves. Tell him which of those was your house.
Whose house felt like a second home when you were growing up?
Why ask it
Plenty of kids had one: the friend whose mom fed everybody, the basement with the good couch. You hear who took him in and what kind of house he found easy to be in, and if that friend is still around you have learned a name that will come up again.
Who was your favorite teacher or coach, and what did they do differently?
Why ask it
The adults he respected outside his own house say a lot about how he likes to be treated. 'He never yelled' and 'she pushed me harder than anyone' point to two different guys. If he is still in school, ask it in the present tense.
Which grandparent, aunt or uncle did you spend the most time with as a kid?
Why ask it
Extended family often gets the warmest stories: the fishing trips, the kitchen he was always allowed into. If that person has died, he may go quiet for a second. Let him, and ask what they were like instead of changing the subject.
Are there little kids in your life, like cousins, nieces or nephews, and how are you with them?
Why ask it
It asks about now, not about whether he wants children, so there is no pressure in it. The guy who gets climbed on at every family party will say so with some pride. 'They scare me' is an honest answer too.
When your whole family gets together, what happens in the first hour?
Why ask it
The first hour has the whole family in it: who cooks, who is late, who restarts the old argument about directions. Listen for the volume, and for where he puts himself, whether that is the kitchen, the floor with the little cousins or out in the driveway with the uncles.
Which friend would you call at two in the morning, and which one would call you?
Why ask it
Two names, and they are not always the same person. The first is who he leans on. The second is who leans on him, and the way he talks about that friend shows whether he likes being needed.
How would your mom, or whoever knows you best at home, describe you to a stranger?
Why ask it
He has to see himself through the eyes of someone who knew him before he was cool. You tend to get the flattering version and the true version in the same breath: 'She'd say I'm sweet and that I never call.'
What he is like
How would you describe yourself in three words?
Why ask it
A classic because the limit forces a choice. The first word is usually the one he is sure of, and the third is where it gets interesting. Offer three for yourself, then ask which of his a friend would swap out.
Do you plan things out ahead of time, or trust that it'll work out on the day?
Why ask it
The proof is in how he packs for a trip or what the morning of a deadline looks like, so ask for one of those. Two planners or two improvisers will get along fine. A planner and an improviser should find out before the first time they try to choose a restaurant together.
Do you tease the people you like, or are you the one who gets teased?
Why ask it
Knowing his style early saves you from taking deadpan teasing as an insult. If he says he dishes it out, ask what is off limits for him in return, since most teasers have one thing they cannot take a joke about.
Neat, messy, or neat in a way only you understand?
Why ask it
The third option is the one most people take, and it comes with a description of a chair covered in clothes that is apparently a system. A low-stakes look at how he lives, and a cheerful thing to disagree about.
What's a pet peeve of yours that I should probably know about?
Why ask it
Funny on the surface and useful underneath, because a peeve tends to point at something he cares about: lateness at time, loud chewing at manners. Confess yours as well, ideally before you find out whether you have been doing his.
Are you a good loser?
Why ask it
Five words, and almost nobody says a flat yes. Expect a story about a board flipped at fourteen or a rematch demanded at midnight. If he claims to be gracious, suggest a game sometime and find out.
What's something you know a ridiculous amount about?
Why ask it
It does not have to be impressive. Grilling, one video game's map, engines, the complete history of one band. He gets to be the expert for a minute, and asking for the beginner's version is a natural next step.
After a whole day around people, are you charged up or completely done?
Why ask it
This gets at the introvert question without the label, which plenty of guys dodge. It tells you whether a quiet Sunday after a party is him losing interest or simply recovering. Let him know which one you are so he can read you too.
How long does it take you to order off a menu?
Why ask it
A silly question, and a handy one to settle before you ask him to pick a movie. There are guys who order in ten seconds and guys still reading when the waiter comes back for the third time. If you are the opposite kind, admit it now and agree on who chooses when you are both hungry.
What's your worst habit, by your own admission?
Why ask it
'By your own admission' keeps it playful and lets him pick something small, like snoozing five alarms. What you are really hearing is whether he can name a flaw with a laugh. Answer it yourself before he has to ask.
What's one thing most people don't know about you?
Why ask it
He chooses how big the secret is, and early on it is usually a harmless surprise: he sings in a choir, he has a twin, he has never seen the ocean. Take the size of his answer as the size to match with yours, and do not fish for a bigger one.
What's a hill you will die on, however small?
Why ask it
The right way to load a dishwasher, the best route across town, whether a hot dog is a sandwich. A guy who can defend his with a grin is easier to disagree with than one who claims he has no strong opinions at all.
When you're annoyed with someone, do you say so or go quiet?
Why ask it
One of the more useful things to know about anyone you might spend time with. There is no right answer, but say which you do, because a talker and a go-quiet person will misread each other until they have compared notes.
After a rough day, do you want company or space?
Why ask it
This tells you what to do the first time he has one. Some people want to be distracted, some want to vent, and some want to be left alone for an hour and then fed. Believe the answer, even if you are the opposite.
What's the fastest way for someone to lose your respect?
Why ask it
Asking from the negative side gets a quicker answer than asking what he values. Lying, being rude to a waiter, bailing on plans: whatever he names is usually a standard he is trying to hold himself to as well. Then ask whether anyone has ever won it back, which tells you if he gives second chances.
What do people thank you for most often?
Why ask it
You find out what he gives without asking him to brag: fixing things, showing up on moving day, making an awkward room laugh. He may need a moment, since plenty of guys have never been asked, and that pause is worth waiting through.
Hopes and plans
What did you want to be when you were a little kid?
Why ask it
Astronaut, pro athlete, garbage truck driver. Ask when it changed, because that is the story of who or what redirected him, and sometimes you find the old dream never fully left.
If you won the lottery tomorrow, what's the first thing you'd do?
Why ask it
The first move is the revealing part: pay off his mom's house, buy a truck, quit by lunchtime, tell nobody. Follow it with month two, once the shopping is over, which is where the real answer tends to be.
Where in the world do you most want to go, and what put it in your head?
Why ask it
The reason matters more than the place. Food, a soccer stadium, the town his grandparents left, a mountain he saw in a documentary. If it is somewhere you have been, resist telling him all about it and ask what he pictures.
What are three things on your bucket list?
Why ask it
Asking for three gets you past the obvious first answer to one he has not said out loud much. Notice the mix of thrills, places and quiet goals. Give him yours and check whether any overlap, which is as good an excuse for a plan as you will get.
What's something you'd love to own one day, however unrealistic?
Why ask it
He is describing the life he imagines as much as the thing: a boat means free weekends, a home studio means time to make something, a field with three dogs means quiet. Ask where he would put it and who gets invited.
What's the dream job, if you let yourself say it out loud?
Why ask it
The wording gives him permission to name the unrealistic one. Do not laugh and do not turn practical on him. Ask what part of it appeals, since 'sports commentator' might really mean he wants to talk about what he loves all day.
Is there an instrument, a language or a sport you wish you'd started as a kid?
Why ask it
This regret is small enough to laugh about, and it often comes with 'I still might'. If he says guitar or Spanish, ask what is stopping him now, and offer to be the audience for the first terrible song.
What do you want to have done by this time next year?
Why ask it
Twelve months is near enough that he will name something he is already working on: a license, a savings number, making the team, moving out. Check in on it a month from now and he will know you were listening.
Do you see yourself working for someone else, or running your own thing one day?
Why ask it
Being his own boss and having a steady team with a paycheck that arrives on time are both fair things to want, and neither needs defending. Ask what the business would be, or what the ideal boss would be like. Either follow-up shows you how he likes to work.
Do you want to end up near where you grew up, or as far from it as you can get?
Why ask it
The answer is as much about his family and his hometown as about geography. 'Close enough for Sunday dinner' and 'a plane ride away' each come with a reason, and the reason is what you are asking for. Give your own answer plainly, since nobody is deciding anything today.
Is there something you've always wanted to build, make or start?
Why ask it
Guys who would never call themselves ambitious often have one of these tucked away: a cabin, a restored car, a video game, a business with a cousin. Ask how far he has gotten, and be the person who does not say it sounds hard.
Where would you like to be five years from now?
Why ask it
The interview version of this makes people stiffen, so ask it over food and keep your tone light. A place, a kind of work, a kind of day: any of them count. Vague is normal at seventeen and at twenty-seven, so listen for direction, not detail.
Whose life would you happily have in twenty years?
Why ask it
He might name an uncle, a coach, a boss or someone famous. Ask what it is about that life: the work, the family, the freedom. You get his picture of a good adult life without making him design one from scratch.
When would you say you've made it?
Why ask it
Most people carry a private finish line: a number in the bank, a house his parents can stay in, a job he does not dread on Sunday night. Tell him yours afterward. The two are rarely the same, and you learn more from the gap than from either answer.
What do you hope you're still doing when you're seventy?
Why ask it
The answer is rarely about work. Still surfing, still meeting the same friends for breakfast, still dancing badly at weddings. It tells you what he never wants to grow out of, and it usually gets a smile on the way.
Deeper
What's something you've pulled off that you weren't sure you could?
Why ask it
A proud moment without the stiffness of asking what he is proud of. It might be a place he got to, a fear he beat or a test he passed on the third try. Let him enjoy telling it, and save your own until he has finished.
What were you afraid of as a kid, and what are you afraid of now?
Why ask it
The childhood half is easy and often funny: the basement, a particular dog. The second half is where he decides how much to trust you. Take whatever he offers, heights or failing or ending up alone, without trying to fix it.
What's been the high point and the low point of your year so far?
Why ask it
Pairing them makes the low easier to say, since he can finish on the high. Go first if he hesitates, and keep your low honest but short. How much he tells you is a fair measure of how comfortable he has become.
Who's a man you look up to, and what does he get right?
Why ask it
It might be a father, a grandfather, an older brother or a coach, and sometimes it is nobody, which is its own answer. 'What does he get right' gets you his working idea of a good man in the form of a real person, and a person is simpler to talk about than a principle.
What's the best decision you've ever made?
Why ask it
It is a proud question that does not ask him to boast, because a decision can be as plain as switching schools, quitting a team or picking up the phone. Ask who thought he was wrong at the time. You find out whose opinion he weighs and whether he can go against it.
What's something you believed a few years ago that you've changed your mind about?
Why ask it
It can be about anything: a career, a friend, his parents, what matters. Listen to how he talks about the person he used to be. A guy who can describe the old view kindly, without sneering at it, tends to be easier to disagree with now.
What's something you had to learn the hard way?
Why ask it
He picks how heavy it is: money, trusting the wrong friend, a car he should not have bought, words he could not take back. Answer with one of yours at about the same weight, so it is a trade and not a confession.
Do you trust people quickly, or does it take you a while?
Why ask it
Neither answer is a warning sign. A slow truster is telling you not to read his caution as coldness, and a fast one has usually been burned at least once and has a story about it. Ask what someone did that earned it, which is more use to you than asking what broke it.
What makes you feel appreciated: hearing it, someone showing up, or something else?
Why ask it
The examples are there because he may never have put it into words. Some guys want the effort noticed without a speech, and some want one specific sentence said out loud. Whatever he lands on is the most practical thing on this page to remember.
Were you raised with a religion, and where do you stand on it now?
Why ask it
Starting with how he was raised gives him a fact to report before an opinion to defend. Listen without debating. If faith matters a great deal to one of you, it is kinder to both to know before you are far in.
What are you good at as a friend, and what are you still working on?
Why ask it
It is about who he is, not what he wants from you, so it is safe to ask before anything is defined. 'I show up' and 'I make things fun' describe different people, and the second half shows whether he can name a weak spot, like going quiet for months, without being pushed. Be ready to answer both parts yourself.
What do you wish people understood about you without having to be told?
Why ask it
The answer is often the thing he gets misread for: quiet taken for unfriendly, joking taken for not caring, busy taken for not interested. Believe it and use it. The next time he does that exact thing, you will know what it means and he will notice that you do.
Is there a chance you didn't take that you still think about?
Why ask it
Expect a team he did not try out for, a move he turned down or someone he never spoke to. Hold the reassurance and ask what he would do with the same chance today, which turns a regret into something he can still act on.
Have you ever forgiven someone who never apologized?
Why ask it
Yes tends to arrive with a parent or an old friend attached, and a no can be just as thoughtful. You are learning how he carries things. Skip it if he has just told you about a falling-out, since it will sound like advice.
What do you want to be known for by the people who know you best?
Why ask it
His answer is the reputation he is aiming for: dependable, funny, someone who made things easier. Tell him one true thing you already see in him, if there is one. He will believe it more for coming right then.
What have you been wondering about me while I've been asking all this?
Why ask it
The turn-around. If he has a question ready, he has been curious too and you can put the list down. If he needs a minute, give it to him, and answer whatever he asks as openly as he answered you.
Getting to know him: how to use these questions
Practical guidance for the conversation itself
Where to start
With a guy you just met
Stay in Everyday life and Favorites. They are facts and preferences he can give a near stranger without thinking twice: where home is, what he is watching, dogs or cats. Two or three are plenty for a first conversation, and the only goal is to find one thing you both want to keep talking about.
With a guy you like
You probably know the basics already, so skip to what you have not heard yet. Family and friends and What he is like are where a crush turns into a person, with a sister, a best friend and a way of handling a bad day. Go slowly. Liking him is a reason to be curious, not a reason to learn everything by Friday.
Over text
The either-or questions travel best by text: sweet or salty, beach or mountains, planner or not. They take a second to answer and he can add as much as he likes. Keep Deeper for when you can hear his voice, because a long typed answer to a big question is a lot to ask of anyone. If you have not met him in person yet, share back your tastes and your stories, and keep your address, your school and your daily schedule general until you have.
Once you have been talking for a while
Hopes and plans and Deeper assume some trust. A good sign that you are there: he has started telling you things you did not ask about. Before that, a question from the last group can feel like being asked for more than the conversation has earned.
Sharing back
Trade, don't collect
Many of the notes tell you what to say about yourself, and they mean it. A conversation where one person asks and the other answers is an interview, however friendly. Give your own answer at about the same length and depth as his, and he gets to know you at the same speed you are getting to know him.
Offer yours before you ask for his
With anything in Deeper, offering your answer before asking for his shows him how much is expected and that you are not just collecting information. Keep yours honest and brief. If he matches it, you have both moved a step. If he stays light, stay light with him.
Follow the detail, not the list
When he mentions a brother, a town or a team in passing, ask about that before you reach for another question. His own details are better prompts than anything written here, and following them shows you heard him.
Use what he told you
Remember one small thing, like his coffee order, the name of his dog or the exam on Thursday, and mention it the next time you talk. Being remembered is a large part of feeling known, and it does more than any single question on the page.
What his answers tell you, and what they don't
Listen for stories and names
A guy who is comfortable tends to answer with people and moments: his cousin, that one summer, the coach who benched him. Short, general answers usually mean he is not there yet, or that the setting is wrong, and neither is a verdict on you.
Notice whether he asks back
One of the clearer signs of interest in a conversation like this is curiosity in return. He does not have to be good at questions. 'What about you?' counts. If it never comes over several conversations, that tells you something none of his answers will.
One answer is not the whole person
He might say he hates planning and then plan a perfect afternoon. People describe themselves loosely, especially when put on the spot. Treat what you hear as a first sketch and let time and how he acts fill it in.
These are not intention questions
Nothing on this page tells you what he wants with you, and trying to read that into his favorite movie will only make you anxious. Knowing who he is comes first. Asking where things are going is a separate, more direct conversation for later.
What gets in the way
Asking ten in a row
A run of questions with no reaction in between feels like filling in a form. Ask one, respond to what he said, add something of your own, and let the next one arrive when the conversation slows. Most good talks use three or four of these, not thirty.
Testing him
If you already know which answer you want, he will feel it. Ask because you are curious what he will say, and let an answer you did not expect be interesting before you decide whether it is a problem.
Pressing when he passes
'I don't know', or a joke in place of an answer, usually means not yet. Say 'fair enough' and go back to something easier. A guy who has been allowed to skip a question is more likely to come back to it on his own.
Going deep to feel close faster
Trading heavy stories in the second conversation can feel like closeness and then leave you both a little exposed the next day. The groups are in that order for a reason. Trust built over a few weeks of easy answers tends to hold up better than trust rushed in one night.