Questions to Ask a Guy
Questions to ask a guy you like, whether he is a boy from class you have just started talking to or someone you have been texting for a while. The 176 questions are grouped by kind: Openers, To get to know him, Funny, Flirty, Deep and Over text, so if you came for deep, flirty or funny questions to ask a guy, you can go straight to that group. Each group runs from easy to harder. Every question comes with a note on why it works or what his answer tends to show, and some notes suggest where to take it next.
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The questions
Each question, and why to ask it
Openers
What's been the best part of your week so far, even if it was something small?
Why ask it
Adding 'even if it was something small' gives him permission to say a sandwich instead of scrambling for an achievement. Ask what made it good and you have your second question for free.
What would you do with a completely free Saturday and nobody to answer to?
Why ask it
Separates the guys who recharge alone from the ones who immediately round up people. Notice whether the day he describes has room for anyone else in it.
What's your go-to order at the place you eat at way too often?
Why ask it
Everyone has a regular spot, and asking about the order instead of the restaurant gets a fast, specific answer. It also quietly hands you a location for a future date.
What's a show or movie you can quote more of than you should be able to?
Why ask it
An easy one to answer, and he will probably prove it on the spot. What he can recite tells you what he grew up watching and who he watched it with, and it hands you a ready pick for a movie night.
Did you play any sports or instruments growing up, and did any of it stick?
Why ask it
Covers the athletes and the band kids in one go without guessing which he was. 'Did any of it stick' usually gets you either a current hobby or a funny story about quitting.
If I visited your hometown for one day, where would you take me first?
Why ask it
He gets to be the tour guide, which is a comfortable role, and you hear how he feels about where he grew up. Pride, eye-rolling and homesickness all sound different.
What's a skill you're trying to get better at right now?
Why ask it
Shows you what he does when nobody is making him do anything. If the answer is 'nothing at the moment', ask what he would pick up if he had a spare hour a day.
Who's the friend you've known the longest, and how did you two meet?
Why ask it
Long friendships say a lot about loyalty and how he handles people changing. The origin story is usually ridiculous, which keeps this firmly in easy territory.
What's your role on a group trip: planner, driver, navigator or snack supplier?
Why ask it
Giving him four options makes it easy to answer in a second, and the choice tells you how he behaves in a team. The guy who says 'I just show up' is telling you something too.
Do you follow a team, and how bad is your weekend when they lose?
Why ask it
Leaves him a clean exit if sport bores him, and plenty of guys are relieved to be asked instead of assumed. If he does follow one, the second half gets you the superstitions, the group chat and the season he still cannot talk about.
What's the first thing you learned to cook, and who taught you?
Why ask it
A practical question in a casual outfit. Whether it was a proper dish or very confident toast, 'who taught you' tends to land on a family story, and you find out whether he cooks now or stopped there.
What's something you own that you use every single day and would replace immediately if it broke?
Why ask it
Headphones, a specific knife, a battered water bottle. The object points to the routine he would be lost without, and a guy who goes quiet on feelings can usually talk about gear for a while.
What was your first car, or the first thing with wheels that you loved?
Why ask it
The first half is easy and the story behind it is the real question: who it came from, where it took him, how it met its end. A first car or bike is usually about freedom, so you hear what that looked like to him.
What's a place near here that you love and hardly anyone seems to know about?
Why ask it
People guard their spots, so being told about one is a small act of trust. If he offers to show you instead of just naming it, that is an invitation and you should treat it like one.
What game do people refuse to play with you anymore, and whose fault is that?
Why ask it
Whether it is Monopoly, mini golf or a quiz night, he is telling you what he is like when he wants to win. 'Whose fault is that' shows whether he can laugh at himself afterward, which matters more than the score.
What's the last thing you got really into, and how far did it go?
Why ask it
Ask this only if you are ready to hear about sourdough or chess openings at length. How he explains it to someone who knows nothing about it is a fair preview of his patience.
Where did you spend most of your time at sixteen when you weren't at home or school?
Why ask it
Naming one age and one place pulls up real memories instead of rehearsed answers: a skate park, a friend's basement, the parking lot behind a fast food place. If he is still around that age, ask where he goes now.
What's the best and worst thing about where you live right now?
Why ask it
You learn what his life looks like outside this conversation: who he lives with, how he spends his evenings, and whether he is settled or itching to move. The best thing is often a taco place downstairs, and the worst is often a roommate.
What's the last thing you did for the first time?
Why ask it
A food, a bus route and a job interview all count, so nobody is stuck for an answer. A long pause is an answer too, and 'what would you like it to be' turns that pause into a plan.
What's an argument you lost that you're now glad you lost?
Why ask it
It can be as small as a band he used to mock or as big as a job a friend talked him out of. What you are listening for is whether he can say 'I was wrong' without a long defense, which is a useful thing to know early.
What do your friends come to you for: advice, a ride, a laugh or a reality check?
Why ask it
He describes himself through other people's eyes, which is easier than describing himself directly. Compare the answer with how he treats you over the next few weeks.
To get to know him
Do you have brothers or sisters, and which of you got away with the most?
Why ask it
The head count is the small-talk half. 'Got away with the most' starts the stories, and an only child will tell you he got away with nothing because there was nobody else to blame.
Do you have a pet, or one you grew up with that you still talk about?
Why ask it
The second half is for the guy whose landlord says no. Ask how the animal got its name, because nobody calls a dog Biscuit without a reason.
What does a normal weekday look like for you, and which part would you keep if you could drop the rest?
Why ask it
Works whether his days are classes, shifts or an office, so you do not have to guess which. The part he would keep tells you what he likes doing, which a job title or a major never does.
What do you listen to when nobody else gets a vote?
Why ask it
Whatever he plays for other people is a compromise. The headphones choice is closer to the truth, even if it turns out to be the same three albums since ninth grade.
What's a food you could eat every day, and one you flatly refuse to touch?
Why ask it
Two facts you will need the first time you pick somewhere to eat together. The refusal usually has a childhood incident behind it, and the incident is worth asking for.
What's your favorite time of year, and what do you do then that you can't do the rest of the time?
Why ask it
A season by itself is small talk. What he does with it is the answer: a lake, a ski pass, a football schedule, or sitting outside late doing nothing at all.
How do you spend an evening when you've got no energy left for anything?
Why ask it
Ask about fun and you get his best weekend. Ask this and you get most of his weeknights: one couch, one game, possibly cereal for dinner.
What trip do you still bring up, and what happened on it?
Why ask it
It does not have to be far away, and a weekend at a cousin's place counts. The trip he keeps retelling is rarely the smoothest one, so listen for whether the best part was the place, the people or the thing that went wrong.
Who in your family do you talk to the most, and what do you two talk about?
Why ask it
Gentler than asking whether he is close with his family, which forces a yes or a no. He picks one person, and how he talks about a grandmother or a little brother previews how he talks about anyone he loves.
What kind of student are you: front row, back row or sprinting in late?
Why ask it
Make it 'were you' for a guy who left school years ago. Class clowns and front-row kids both tend to own up proudly, and you can usually still see it in him.
What do you and your closest friends do when there's nothing to do?
Why ask it
Driving around, the same video game, sitting in somebody's kitchen. A friendship shows most in its default setting, and this is the setting you would be joining.
What are you good at that nobody would guess from looking at you?
Why ask it
He gets to show off something he never gets asked about, like baking or reversing a trailer or settling a crying baby. Act impressed only if you are, because he will be able to tell the difference.
What's something you've stuck with for years and still aren't bored of?
Why ask it
New interests are easy to list. A sport since he was six, a guitar or the same Saturday job says more about what holds his attention once the novelty has gone.
Would you call yourself shy, outgoing, or does it depend on the room?
Why ask it
Most people take the third option, so have 'which rooms?' ready. You find out where he is loudest, where he goes quiet, and roughly where talking to you falls between the two.
What's the last thing you saved up for, and was it worth it?
Why ask it
Saving up means he wanted it for a while, so you hear what he will wait for: sneakers, a console, a first month's rent. 'Was it worth it' tends to get a grin or a wince, with nothing in between.
What did you do last summer that you'd happily do again?
Why ask it
A narrow window jogs the memory better than 'what do you like doing'. If the answer is a job he hated plus one great week, ask about the week.
What's your favorite holiday, and what does your family always do for it?
Why ask it
'Always' brings out the odd rituals: the yearly argument about the tree, a dish only one uncle eats. If holidays are not a happy subject at his house, his tone will say so quickly and you can change the subject without pressing.
What job would you be surprisingly good at that has nothing to do with your life now?
Why ask it
Friendlier than asking about a dream job, since it does not have to be realistic. A guy who says wedding DJ or park ranger has told you what he would do with his days if nobody were keeping score.
If you could live anywhere for one year, where would you go and what would you do there?
Why ask it
The one-year limit makes it a plan and not a postcard. A big city, a surf town and two streets from his mom are three different levels of restless.
What's the most spontaneous thing you've ever done, and who talked you into it?
Why ask it
For one guy this is a road trip decided at midnight, and for another it is ordering something new at the usual place. Both are worth knowing, since they show how much warning he likes before a plan changes.
What was the last thing that made you laugh until it hurt?
Why ask it
He will try to retell it and it will not be as funny, and watching him laugh at it again anyway is the good part. Note who was with him at the time: those are the people he is most relaxed around.
What's the story your family tells about you at every single get-together?
Why ask it
Every family keeps one, usually about something he did at five. He will act tired of it and then tell the whole thing, voices included.
What's the first way you ever earned your own money, and what did you spend it on?
Why ask it
Mowing lawns, a paper round or selling sweets at school at a markup: the first money a guy earns usually comes with a story about how fast it went. You also hear how he feels about work without asking about a career.
What small thing can a person do that makes you like them right away?
Why ask it
Holding a door, remembering a name, laughing at their own bad joke. It is his list of what he values in people in miniature, and nothing stops you from doing one of them next week.
What was the strictest rule in your house growing up, and what did you get away with anyway?
Why ask it
You get a sketch of the home he grew up in, curfew and grades and shoes in the hall, without asking him to pass judgment on it. Often you also hear which of those rules he still keeps.
What do people usually get wrong about you when they first meet you?
Why ask it
Quiet guys get read as unfriendly and loud ones as full of themselves. He is handing you the correction in advance, so you can skip the wrong impression everyone else had to work through.
What matters most to you in a friend?
Why ask it
Short to ask and worth hearing in full. Loyalty, honesty and 'someone who shows up' are three different answers, and what he asks of his friends is roughly what he will hope for from you.
What are you working toward right now, and how far off is it?
Why ask it
A team spot, a certificate, a savings number, a band that practices in a garage: you see what he is willing to be tired for. Ask how it is going now, then again in a few weeks.
What's the best advice you've been given that you still use?
Why ask it
'That you still use' filters out the poster slogans. What is left tends to be one sentence from a grandfather or a boss, and he can usually tell you the first time it came in handy.
What should I have asked you by now that I haven't?
Why ask it
After a run of your questions, he gets to choose the subject. Whatever he names, ask it right then, because he has just told you what he most wants to talk about.
Funny
What's the worst idea you and your friends ever thought was brilliant?
Why ask it
He almost certainly has one and has been waiting for an excuse to tell it. The best versions involve a shopping cart, a roof or a plan that started with 'it will be fine'.
What do you take way more seriously than it deserves?
Why ask it
Fantasy football, packing the car trunk, the right way to build a burger. Tease him about it on purpose: a low-stakes argument is the quickest way to find out how he argues.
What's the most useless talent you have, and can I see it?
Why ask it
Asking to see it is the point. A guy who will wiggle his ears or do his impression of one particular teacher in public is comfortable looking silly around you.
What movie did you see way too young, and what did it do to you?
Why ask it
An older cousin or a sleepover is usually to blame. A guy who can admit that a film about a shark kept him out of the deep end for two summers is easy company, so ask whether he has dared to watch it since.
What's the worst photo of you that somebody else treasures?
Why ask it
Asking who treasures it turns a one-line answer into a story with a villain: a mother with a frame, a friend with a group chat. Request photographic evidence only if you are prepared to supply your own.
What's a task you were sure would take ten minutes and swallowed the whole day?
Why ask it
Assembling a shelf, a software update, finding one document for one form. The overconfidence is what makes it funny, and a guy who tells this one well is not too proud to be around.
What food combination do you defend that everybody else finds upsetting?
Why ask it
A harmless confession, whether it is peanut butter on a burger or cereal with orange juice. How hard he campaigns for it shows how much he enjoys being the odd one out.
What's the laziest thing you've ever done to avoid getting up?
Why ask it
He will tell it with pride, which is the only way to tell a story about hooking the remote with a hockey stick or phoning someone in the next room.
What do you say you're pretty good at that you've only done about twice?
Why ask it
The laugh comes first, because he already knows which claim is shakiest: skiing, pool, a language, anything on a grill. The brave follow-up is to suggest the two of you go and test it.
If you were on a heist crew, what job would you get, and what job would you think you deserved?
Why ask it
The gap between the two answers is the joke and also the insight. Mastermind in his head, getaway driver who stops for snacks in reality: that is a man with a sense of proportion.
When you have a cold, do you carry on as normal or start drafting your will?
Why ask it
He knows exactly which one he is, and so does everyone who has lived with him. If he claims to carry on as normal, ask who would back that up. It is also a preview of what looking after him involves.
What's the worst gift you've ever given someone, and how did they take it?
Why ask it
Asking about one he gave, not one he got, makes him the fool of the story instead of someone else. It is also a gentle way to find out whether he learned anything from it.
If you came with a warning label, what would it say?
Why ask it
'Gets quiet when hungry.' 'Will not ask for directions.' It is a joke format, but people are surprisingly honest inside it, so file the answer away for later.
What did teachers write on your report card every single year?
Why ask it
He can usually quote it word for word: 'easily distracted', 'could do well if he applied himself'. Whether he says it with pride or a wince tells you if he thinks the teachers were right.
What's the most 'dad' thing you already do?
Why ask it
It is teasing he walks into by himself: checking the door twice, admiring a good parking spot, saying 'right' before he stands up. Most guys have caught themselves at one of these.
What totally normal thing do you somehow look suspicious doing?
Why ask it
Walking out of a store without buying anything, carrying a ladder, waiting in a parked car. It gets him laughing at himself without asking him to confess to anything real.
What temporary fix of yours has quietly become permanent?
Why ask it
The answer usually comes with a defense of why the tape on the car mirror or the charger that only works at one angle is fine the way it is. The defense is the fun part.
What do you do alone in the car that you'd deny if anyone asked?
Why ask it
The car is the one room where nobody can hear him, so that is where the full concerts and the arguments with people who are not there take place. If he admits to singing, ask what the opening number is.
Where's the weirdest place you've ever fallen asleep?
Why ask it
A short story with a built-in ending, since somebody always had to wake him: a bus driver at the last stop, a teacher, a very surprised relative. Safe to ask anyone at any stage.
What's your least believable true story?
Why ask it
The one he has stopped telling because nobody buys it: a celebrity at a gas station, a goose that followed him home. Promise to believe him before he starts, then try to keep the promise.
What minor inconvenience would be your villain origin story?
Why ask it
Slow walkers, a self-checkout that needs assistance, someone replying 'k'. You get a map of his pet peeves without the conversation turning into a list of complaints.
What name have you been called by mistake so often that you now answer to it?
Why ask it
It starts with a coffee shop spelling, a teacher who never learned it or a friend's grandmother who decided he was Kevin. Ask whether he ever corrected them and how long he let it run.
What's the most elaborate excuse you invented as a kid, and did it work?
Why ask it
'Did it work' matters. A guy whose story collapsed instantly tells it differently from one who got away with it, and both are funnier than anything he would say about himself as an adult.
If your life had a narrator, what would they sigh about the most?
Why ask it
The narrator lets him criticize himself in the third person, which is far easier than doing it straight. 'Once again, he did not write it down' is the kind of answer you are hoping for.
What have you been doing wrong your whole life until somebody finally showed you?
Why ask it
The moment of being corrected is always a scene, whether it was tying his shoes, peeling a banana or saying a word he had only ever read. He can only tell it well if he is over it.
What record do you hold that nobody else is trying to beat?
Why ask it
A pointless record defended seriously is a reliable laugh: most pancakes in one sitting, most umbrellas lost in a year, fastest exit from a family gathering. Ask for the exact numbers.
When you realize you're walking the wrong way, how do you turn around without looking lost?
Why ask it
Everyone has a technique: the fake phone check, the pat of the pockets, the full commitment to the wrong direction. His choice is a tidy summary of how he handles embarrassment.
What's the weirdest thing you own and refuse to get rid of?
Why ask it
A traffic cone, a trophy for something he did not win, a broken lamp with sentimental value. The refusal is the story, so ask what it would take for him to let it go.
If a zombie movie started right now, what within arm's reach would you grab first?
Why ask it
He will look around, take inventory out loud and badly overrate a fork. It works in any room, and his pick shows whether he plans to fight, hide or negotiate.
How long would you last on a reality show, and what would get you sent home?
Why ask it
He knows his own weak spot: too honest, too lazy, a fight over the dishes in week one. Ask which show he was picturing, because a baking tent and a desert island are very different ways to fail.
What's the pettiest reason you've ever gone off a song, a show or a snack?
Why ask it
Someone he disliked loved it, or a roommate played it every morning for a semester. Pettiness admitted cheerfully is charming. Pettiness defended at length is a small flag.
What would you definitely be arrested for if being mildly annoying were a crime?
Why ask it
He is telling you in advance what his friends already tease him about, whether that is narrating movies, drumming on tables or correcting song lyrics. It saves you discovering it in month three.
What did you get blamed for that you still insist wasn't your fault?
Why ask it
Everybody has one case they would like reopened. Expect a full defense with witnesses, and enjoy how annoyed he still is about a broken window from years ago.
What would you be famous for if you got famous completely by accident?
Why ask it
Accident rules out talent, so he is left with a blooper on the local news, a very public fall or a complaint letter that got out of hand. It is how he thinks he looks on a bad day, told as a joke.
What's a joke you made that went so badly you still think about it?
Why ask it
A quiet room, a punchline nobody wanted, a long walk back to his seat. You find out what his sense of humor does when it is off the leash, and whether he can tell a story where he is the one who got it wrong.
Flirty
What was your first impression of me, and how far off was it?
Why ask it
The second half gives him room to tease you and to admit he has been thinking about you since. Be ready to answer it back, because he will ask.
What's the fastest way to make you smile when you're in a terrible mood?
Why ask it
Practical flirting: you are openly collecting instructions for later. If he says 'honestly, just food', believe him and remember what kind.
What's the cheesiest pickup line you know, and would it work on you?
Why ask it
He delivers a terrible line, you both groan, and nobody has had to be sincere yet. 'Would it work on you' is the real question, and the honest answer is often yes.
Would you share your fries with me, or is that a later stage?
Why ask it
A silly question about how comfortable he is. 'Later stage' means he is already picturing stages, which answers something you did not ask.
What's your idea of a great date that costs almost nothing?
Why ask it
Taking money off the table shows whether he has any imagination. It also tells him, without saying so, that you are not keeping a tab on what he spends.
Are you better at giving compliments or taking them?
Why ask it
A guy who says 'neither' is telling the truth and is about to get flustered. Whichever he picks, test the other one right away and watch what his face does.
What's your most charming quality, according to you?
Why ask it
'According to you' lets him brag as a joke. Agree with his pick or offer a different one: telling a guy what you find charming about him is about as direct as playful gets.
Which of us makes the other one laugh more?
Why ask it
A contest where losing is also a compliment. He will claim the title, you will dispute it, and arguing over who is funnier is flirting under another name.
What do you own that you know you look good in, and when do I get to see it?
Why ask it
He gets to boast a little, and the second half turns the boast into an invitation. You also find out what he thinks he looks good in, which is not always what you would have guessed.
How would you describe your flirting style: smooth, awkward or accidentally insulting?
Why ask it
He has to admit to having a style at all, which is the point. If he picks awkward, ask for evidence: a story about a time it went wrong is usually better than any success, and he will be wondering how he is doing right now.
What would I have to cook, order or bring over to win you over completely?
Why ask it
Low pressure, high usefulness. The answer is a ready-made plan for dinner, and you should expect a level of detail here that he gives to almost nothing else.
If I picked the restaurant and you picked the movie, which of us should be more worried?
Why ask it
A date proposed sideways, as a joke about taste. He will either insult your restaurants or defend his movies, and now the two of you are discussing a particular evening.
What do you think you could beat me at, and what does the winner get?
Why ask it
Name the game on the spot: air hockey, a card game, a race to the corner. A challenge with a small prize is an invitation that never has to be called one, and he gets to pick the stakes.
Do you make the first move, or do you wait until the hints are impossible to miss?
Why ask it
Ask this when you would like to know whether you are going to have to do it yourself. If he admits he misses hints, consider that your cue to stop being subtle.
What do you usually notice first about someone you end up liking?
Why ask it
Worded about 'someone' so he can answer safely, though you will both know who is being discussed. Listen for whether he names a look, a habit or a feeling.
What's your tell when you like someone, so I know what to watch for?
Why ask it
The closing clause is the flirt: it announces that you will be watching. Some guys go quiet, some get loud, and some suddenly develop opinions about your favorite band.
How would you get my attention from across a crowded room?
Why ask it
An easy scene to picture: a wave, a terrible dance, a text that says 'look left'. You learn whether he is a grand-gesture person or a quiet one, and he learns you would like him to try.
Would you rather get a good morning text or a good night call?
Why ask it
Either answer is something you can act on by tomorrow. If he says both, he is not being greedy. He is telling you he likes hearing from you.
If we had one whole day and you were in charge of the plan, what are we doing?
Why ask it
Putting him in charge flatters him and tests him at once. A vague answer means he has not pictured it yet. A detailed one means he has, probably more than once.
What's a nickname I could call you that you'd pretend to hate?
Why ask it
'Pretend' does the heavy lifting: it invites him to pick one he secretly likes. Use it sparingly afterward. A nickname only works while it still feels like a privilege.
What should we try together that neither of us is any good at?
Why ask it
Being bad at bowling or pottery or ice skating together takes away the pressure to look impressive. It also becomes a plan the moment one of you says 'when'.
What's the worst date idea you'd still say yes to if I asked?
Why ask it
A three-hour documentary, a hike at six in the morning, a craft fair. The joke is that he would come anyway, and saying so out loud is the compliment.
What's the best compliment you've ever received that you still think about?
Why ask it
The compliment a guy holds on to is often years old and oddly specific. It shows what he wants to be seen as, and gives you a clear target if you feel like adding to the collection.
What's something about you I'd only find out around the third date?
Why ask it
Suggests there will be a third date without actually asking for one. He gets to decide how much to reveal, and whatever he teases here you can hold him to later.
What would you want to teach me if we had a free afternoon?
Why ask it
Most people enjoy being good at something in front of someone they like. His pick shows what he is proud of, and whether he pictures himself as a patient teacher or a show-off.
How would you describe me in three words to someone who has never met me?
Why ask it
Three words is too few to hide behind. If 'funny' or 'trouble' is one of them you are doing fine, and you owe him three in return.
What's your favorite thing I've said to you so far?
Why ask it
You find out which version of you landed: the joke, the tease or the thing you said by accident. If he can quote it word for word, he has been replaying it.
What did your friends say when you first mentioned me?
Why ask it
A bold one, because it assumes he has mentioned you. If he has, you get a secondhand review. If he stammers, you have learned something equally useful and he now has homework.
What's a song you'd put on a playlist for me, and why that one?
Why ask it
The 'why' is where the flirting lives. A song chosen because it is good is one thing. A song chosen because it reminds him of you is a confession with a chorus.
What's something small you've noticed about me?
Why ask it
It asks for a compliment without using the word. The answer is rarely about looks: more often it is how you say a certain word or what your hands do when you are thinking, and it shows he has been paying attention.
If I borrowed your favorite hoodie, how long before you'd ask for it back?
Why ask it
A hoodie on loan is a well-understood claim, and he knows it. 'Never' is the answer you are hoping for, and 'which hoodie' means he is already choosing one for you.
What do you think our first silly argument would be about?
Why ask it
Imagining a harmless future fight is oddly intimate, since it assumes there is a future to fight in. Thermostat settings and driving directions are the usual suspects.
What should I know before I meet your friends?
Why ask it
Listen to the briefing: who will tease you, who to sit beside, which story not to bring up. A guy who answers in that much detail has already pictured you in the room.
When did you work out that I was flirting with you, or is this the moment?
Why ask it
Says the quiet part out loud, with a joke attached so he can laugh instead of freezing. If he claims he knew all along, ask what gave you away.
What's a question you'd like to ask me but keep talking yourself out of?
Why ask it
Hands him the wheel. He may dodge with a joke, but the first thing that crossed his mind before the joke is what he wanted to ask, so give him a second to get there, and be ready to answer it when he does.
Deep
When were you happiest in the past year, and where were you?
Why ask it
It asks for a good memory, so it goes deep without being heavy. Where he was and who was with him show what happiness is made of for him: a crowd, one person, or nobody at all.
Who shaped you the most growing up, and what did you take from them?
Why ask it
He might name a parent, a coach or an older cousin. 'What did you take from them' keeps it from becoming a biography and leaves room for the things he decided not to copy.
What are you proudest of that would never show up on a resume?
Why ask it
Moves him off job titles and onto character: helping a brother through a bad year, showing up for a friend, quitting something that was bad for him. Do not rush to fill the pause before he answers.
What do you do exactly the way your mom or dad does, whether you like it or not?
Why ask it
A laugh, a way of loading the dishwasher, the exact tone he uses when he is annoyed. It starts light and can end up somewhere real, and 'whether you like it or not' tells him both kinds of answer are welcome.
What's something you've worked hard to change about yourself?
Why ask it
Anyone can list flaws. You are listening for evidence that he noticed one, a temper or a habit of going silent, and then did something about it.
What would you like to be trusted with that nobody has handed you yet?
Why ask it
What a guy wants to be trusted with shows who he is trying to become: the car, a harder shift, a say in a family decision. Listen for whether he feels people still see an earlier version of him.
What would you tell yourself from a few years ago, knowing he probably wouldn't listen?
Why ask it
The 'wouldn't listen' part gets a laugh and then an honest answer. The advice is usually to worry less about one particular thing, and that thing is what those years were like for him.
What's a failure you're grateful for now?
Why ask it
Time has usually sanded this one into a good story, so it is a safe way in to a hard subject. Notice whether he blames other people or owns his part of it.
What's an expectation people put on guys that has never really fit you?
Why ask it
Being stoic, loving sports, always having a plan. Hardly anyone asks him this, and the relief of answering it tends to show. Do not argue with whatever he says.
What does being a good man mean to you, in your own words?
Why ask it
Ask it out of curiosity and not as a test with a right answer. He has probably been handed several definitions and had to choose among them, and whose example he reaches for shows who he measures himself against.
What makes you feel respected, and what makes you feel talked down to?
Why ask it
Respect is a word people use for very different things. Being asked his opinion, being trusted with something, not being teased in front of others: after this you know his version and can stop guessing.
What did your family teach you about relationships, whether they meant to or not?
Why ask it
'Whether they meant to or not' lets him talk about bad examples as well as good ones. Save it for when you have proper time, because a rushed answer to this helps nobody.
Who can tell you're not okay even when you insist you're fine?
Why ask it
If he has a person, you learn who has earned that kind of closeness and what they do with it: push, wait, turn up with food. If he says 'nobody, I hide it well', you have learned how he copes, and what being close to him may involve.
When was the last time you cried, and what set it off?
Why ask it
Ask it plainly, without a teasing tone, or he will answer with a joke. A movie about a dog counts. What matters is whether he can say it without apologizing for it.
What's a decision you made mostly to keep someone else happy?
Why ask it
It is a heavy one, because the honest answers are a degree, a city or a relationship he stayed in too long. Offer your own answer first if he hesitates, which makes it a trade instead of a test.
Who showed up for you when things were at their worst, and what did they actually do?
Why ask it
'What did they actually do' moves him past 'my mom, she was great' to a lift to the hospital or a couch for three weeks. That is what support looks like to him, described by someone who has been on the receiving end.
When did you stand up for someone, or wish afterward that you had?
Why ask it
For most people the second half is the more honest one. Whichever he tells, you learn what he thinks he owes to somebody being treated badly, and that matters more than how brave the story sounds.
How do you act when something's really bothering you, and what helps?
Why ask it
One of the most useful questions here if this is heading anywhere. Some guys want space, some want distraction, and few people will tell you which in the moment, so ask while things are calm.
What's a friendship you lost that you still think about?
Why ask it
Friendships often end by drift instead of drama, and those endings rarely get talked about. How he tells it shows whether he can miss someone without needing to be the wronged party.
What do you have right now that you'd hate to lose?
Why ask it
Imagining something gone is an easier way to name what he values than being handed the word 'values'. Expect a friendship, a place on a team, the dog, or the fact that his family still eats together on Sundays.
Who do you most want to make proud?
Why ask it
Quick to ask, and the answer is often somebody he rarely mentions: a grandfather, a coach, a younger sister. If he says 'myself', ask who it used to be.
What part of your life looks nothing like you expected it to?
Why ask it
Works for good surprises and hard ones, and he gets to choose which to tell you about. Follow up with 'do you mind that' instead of assuming he does.
What's something you do for other people that you'd never ask anyone to do for you?
Why ask it
Driving across town at midnight, lending money without a word, listening for an hour. It shows you what registers as care to him, and the second half tells you what he finds hard to accept, which is worth knowing before you offer it.
What would you try if you weren't worried about looking foolish?
Why ask it
The thing he names, whether it is dancing, a career change or saying something out loud, is usually closer to a real wish than any answer to 'what are your goals'.
What's a promise you've made to yourself?
Why ask it
Never to shout the way someone shouted at him, to leave his hometown, to finish what a parent could not. A promise like that steers a lot of decisions, and he may never have said this one out loud.
What does a good life look like to you in ten years, leaving job titles out of it?
Why ask it
Removing job titles forces him to describe a day instead of a position: where he lives, who is around, what a Tuesday feels like. Compare notes honestly, not hopefully.
What kind of dad do you think you'd be, if you want to be one at all?
Why ask it
Say the 'if' out loud, because he may not want kids and that is worth knowing early if you do. A guy who does will describe either the father he had or the opposite of him, which tells you about the house he grew up in.
What were you like in your last relationship that you'd want to do differently?
Why ask it
Asks about him, not about his ex, which keeps it from becoming a review of someone who is not there. A guy who can name his own part has done some thinking. One who cannot has told you plenty too.
What does a good relationship look like to you on a boring weeknight?
Why ask it
Anyone can describe a perfect anniversary. A weeknight is where it is lived: who cooks, how much you talk, whether you are happy in the same room doing separate things. Notice how closely his picture matches yours.
What do you need to hear more often than you do?
Why ask it
Often it is 'thank you', 'you are doing fine' or 'I am proud of you'. It is a vulnerable thing to admit, so receive it quietly, and at some later point say it to him and mean it.
What do you worry about that you'd never bring up with your friends?
Why ask it
Money, a parent's health, whether he is falling behind everyone else. Plenty of guys keep one set of subjects for the group and another for nobody, so being trusted with the second set means something. Listen, and leave the fixing for another day.
When do you feel lonely, if you ever do?
Why ask it
'If you ever do' gives him a way out, and having one makes it likelier he will not use it. Sunday evenings and crowded parties are both possible answers. You are not being asked to solve it, only to hear it.
What do you only do around people you completely trust?
Why ask it
He will name a behavior: telling them bad news first, sitting in silence comfortably, handing over his phone without thinking. That behavior is the milestone to watch for between you.
Over text
What are you doing right now, and what would you rather be doing?
Why ask it
The second half rescues the dullest opener in texting. 'Laundry' is a dead end, but 'laundry, and I would rather be on a beach' gives you somewhere to go.
What's the honest first ten minutes of your morning like?
Why ask it
Easy to type, mildly confessional, and nobody's true answer is meditation. Send it early in the day and it doubles as a good morning message with something to reply to.
Send me a photo of the view from where you are. What am I looking at?
Why ask it
Asking for the view instead of a selfie keeps it easy and unposed. You will get a desk, a dashboard, a dog on a couch or a very dull wall, and each one comes with an explanation.
What's the most recent thing you wrote in your notes app, and what on earth was it for?
Why ask it
Answerable in ten seconds because he can just look, which is what a text question should be. A gate code, half a shopping list, a band name for a band that does not exist: it is a small, unposed look at what goes through his head.
What song have you had on repeat this week, and should I be worried about you?
Why ask it
The teasing second half shows him your tone, which text otherwise hides. Listen to the song and reply with a verdict, and you have turned a question into a running bit.
What should I watch tonight, given that you get one pick and all the blame?
Why ask it
Gives him a job, and a task often gets a quicker reply than a feeling does. It also books tomorrow's conversation, because you will owe him a review.
What's your texting style: instant reply, or three to five business days?
Why ask it
Asked early, this saves a lot of reading into silence later. If he admits to being slow, you know a gap means he is busy, not that he has gone off you.
What's the worst thing autocorrect has ever sent on your behalf?
Why ask it
The best ones were sent to a boss, a teacher or somebody's mother. It suits a text thread because the two of you are one typo away from adding to the list.
What's one thing that's been sitting on your to-do list for over a month?
Why ask it
A renewal, a dentist appointment, a shelf that is still in its box. It is a relatable confession, and checking in on it a week later shows you were listening.
What three things would I find in your fridge right now?
Why ask it
Lists are easy to type and oddly revealing. Condiments and nothing else, a carefully prepped week of lunches, a single lime: each of these is a different guy.
What photo on your phone would take the longest to explain?
Why ask it
A parking level, a receipt, a dog mid-sneeze: the camera roll is full of pictures taken for a reason nobody else could guess. Let him decide whether to send the photo or just describe it.
If today were a chapter in a book about you, what would the title be?
Why ask it
Beats 'how was your day' because he cannot answer 'fine'. 'The Printer Wins Again' tells you about the day and about his sense of humor in four words.
What's an opinion you'd happily type but would never say out loud at a party?
Why ask it
Uses the one advantage text has: distance makes people braver. Expect something like 'sunsets are overrated', and be prepared to defend sunsets.
What's the last thing you put in an online cart and then talked yourself out of?
Why ask it
A window into what he wants versus what he lets himself have. Works well by text because he can go and check, and the true answer is usually funnier than the remembered one.
What's your lock screen right now, and how long has it been that?
Why ask it
A photo he chose to look at all day long is a quick read on what matters to him. 'The default one, since I got the phone' is also a complete personality.
Two truths and a lie, text edition: can you send three and let me find the fake?
Why ask it
Typing strips out the giveaway grin, so the game is harder and better by text. You walk away with two new true facts about him whichever one you pick.
What time do you really go to sleep, compared with what you tell people?
Why ask it
Useful scheduling information dressed up as a joke. It also tells you when a late message will be read right away and when it will be found at breakfast.
Are you a voice note person, or do they sit unplayed on your phone for days?
Why ask it
Worth knowing before you record a three-minute one. If he likes them, send one: a voice carries tone that typing cannot. If he dreads them, you have spared you both.
If I called you right now, would you pick up or stare at the phone in horror?
Why ask it
A playful way to find out whether he is a phone call person before you try it. If he says he would pick up, you are allowed to test that within the hour.
What's the group chat you're most active in, and what is it mostly about?
Why ask it
His group chat is where he is least edited. Whether it is fantasy league trades, family logistics or an endless stream of bad jokes, you learn who has his attention on an ordinary day.
What's today out of ten so far, and what would bump it up a point?
Why ask it
Feelings are awkward to type and a number is not. A seven needs nothing from you. A three tells you to ask what happened, and the second half tells you whether there is anything you could do about it.
What's something you nearly texted me this week and then didn't send?
Why ask it
The boldest question in this section, so keep it for when the thread is already warm. Drafts that were never sent are usually either a joke he doubted or something sincere.
How to ask a guy questions without it feeling like a quiz
Practical guidance for the conversation itself
Picking the right question for the moment
Start at the top of each group
Every tag runs from easy to harder, so the first few questions under each heading are safe almost anywhere. Keep the last few in Deep and Flirty for when he has already shown he is comfortable with you.
Ask while you are doing something else
Bigger questions go down easier when you are both doing something else: walking, driving, cooking, waiting in a line. With somewhere else to look, a guy who would freeze across a table will often just start talking.
Ask for the story, not the fact
If a question gets you a one-word fact, the follow-up that works is about a moment: when did that start, who was there, what happened next. Stories are easier to tell than opinions, and he will forget he is being asked things.
Ask one, then stay with it
The list is long so that you can choose, not so that you can get through it. A single question that turns into half an hour of conversation has done more than ten asked in a row.
Three situations and a plan for each
The first-conversation warm-up
- 1Pick two Openers whose answers you are honestly curious about.
- 2Ask the first one, then follow up on a detail he mentioned instead of moving on.
- 3If the mood is good, try one from To get to know him or one from Funny.
- 4The moment he asks you something back, put the list away. It has done its job.
The long drive or walk
- 1Start with Funny so you are both laughing at yourselves early.
- 2When there is a natural lull, try one question from the first half of Deep.
- 3Let silences run. On a drive, a pause is him thinking, not him refusing.
- 4Finish on something light so the heavier answer does not hang over the rest of the day.
A text thread that lasts all week
- 1Send one Over text question a day at most, at a time he is likely to be free.
- 2Reply properly to his answer before you ask anything else.
- 3Every few days, swap the question for a photo or a comment on something he told you earlier.
- 4Keep the Deep questions off the phone. Typed answers to big questions tend to come out shorter and more guarded than spoken ones.
When it stalls
When you get a one-word answer
Do not read it as lack of interest straight away. Narrow the question instead: offer two options, or ask about last weekend in place of weekends in general. Some people need a smaller target to hit.
When he jokes his way out of a Deep one
Laugh, because it was probably funny, and let it go for now. A joke is often a request for more time, not a refusal. Ask again another day in a quieter setting and you will usually get the real answer.
When a Flirty question lands flat
Own it with a smile and move on: 'Okay, that one sounded better in my head.' Being able to miss without getting flustered is attractive in itself. Go back to Funny for a while before you try again.
When it starts to feel like an interview
The sign is that you are asking everything and he is answering everything. Stop asking for a while. React to what he has said, tell a story of your own that his answer reminded you of, and see whether he gets curious.
When the text thread goes quiet
Do not stack a second question on top of an unanswered one. It turns a slow reply into pressure. Wait a day, then send something that needs no answer, and let him pick the thread back up.