Questions to Ask a Guy
For anyone getting to know a guy they like, whether you met last week or have been texting for a while. The questions are grouped as Openers, Funny, Flirty, Deep and Over text, and each group runs from easy to harder. Every question comes with a note on what his answer tends to show and what to ask 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 something you're weirdly good at that almost never comes up?
Why ask it
Parallel parking, folding fitted sheets, guessing the time without a clock. 'Weirdly' keeps it from sounding like a job interview and lets him brag without feeling like he is bragging.
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.
What's the best meal you can make without looking anything up?
Why ask it
A practical question in a casual outfit. Whether it is a proper dish or very confident toast, follow with 'who taught you that' and you often land on a family story.
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 did you want to be when you were a kid, and when did that plan change?
Why ask it
The first half is cute and the second half is the real question. The moment the plan changed is often the first big decision he made, or the first one made for 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's the last thing you got way too competitive about?
Why ask it
Mini golf, a quiz night, a parking space. You find out whether he can laugh at himself afterward, which matters more than whether he won.
What could you talk about for an hour with zero preparation?
Why ask it
Ask this only if you are ready to hear the answer at length. How he explains the thing he loves to someone who knows nothing about it is a fair preview of his patience.
What's a smell that instantly takes you back somewhere?
Why ask it
Cut grass, a gym bag, his grandmother's kitchen. Smells tend to pull up real memories instead of rehearsed answers, so it feels personal without feeling like prying.
What are you looking forward to in the next month or so?
Why ask it
A guy with something on the calendar is easy to talk to, and a guy with nothing on it may be telling you he is in a rut. Either way you learn what his life looks like outside this conversation.
What's something you changed your mind about in the last year or so?
Why ask it
It can be as small as a band he used to mock. 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.
Funny
What's the dumbest way you've ever hurt yourself?
Why ask it
Every guy has one and has been waiting for an excuse to tell it. The best versions involve a sibling, a bicycle or a piece of furniture he was sure would hold.
What's a hill you will die on that matters to absolutely nobody?
Why ask it
Whether a hot dog is a sandwich, how to load a dishwasher, which way the toilet paper hangs. Disagree with him on purpose: a low-stakes argument is the quickest way to find out how he argues.
What was your worst haircut, and who let you leave the house with it?
Why ask it
Asking who was responsible turns a one-line answer into a story with a villain. Request photographic evidence only if you are prepared to supply your own.
What's the most confidently wrong you've ever been?
Why ask it
The 'confidently' is what makes it funny: directions he refused to check, a fact he bet on, a shortcut that added an hour. 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
Peanut butter on a burger, fries dipped in a milkshake, cereal with orange juice. It is a harmless confession, and how hard he campaigns for it shows how much he enjoys being the odd one out.
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.
What did you believe as a kid for far longer than you should have?
Why ask it
That the ice cream truck only plays music when it has sold out, that teachers lived at the school. Whoever planted the idea is usually a parent or an older sibling with a good sense of humor.
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.
What would the warning label on you 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 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's the worst thing you've ever cooked for another person?
Why ask it
The answer usually comes with a victim and an apology that is still ongoing. If he has never cooked for anyone, that is an answer too, and possibly a project.
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 word did you mispronounce for years before somebody finally told you?
Why ask it
Usually a word he learned from reading, which is a nice thing to find out by accident. Ask who corrected him and how gently: there is always a scene.
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's your recovery move when you wave back at someone who was waving at the person behind you?
Why ask it
Everyone has done it and everyone has a technique: the hair fix, the stretch, the full commitment to greeting a stranger. 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.
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
Narrating movies, drumming on tables, correcting song lyrics. He is telling you in advance what his friends already tease him about, which saves you discovering it in month three.
What's the last thing you laughed at when you absolutely should not have?
Why ask it
A quiet room, a serious meeting, someone tripping with great dignity. You find out what his sense of humor does when it is off the leash, and whether it is kind underneath.
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 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 a small thing someone can do that gets your attention immediately?
Why ask it
Remembering a detail, laughing with their whole face, being kind to a waiter. You are asking what works on him while leaving him a little unsure whether you plan to use it.
What's the cheesiest line that would honestly still work on you?
Why ask it
He has to admit to having a soft spot, which is the point. Deliver the line back to him a week later, deadpan, and see whether he was telling the truth.
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.
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 notice first when you're starting to like someone?
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.
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'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.
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.
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 were you hoping I'd ask you by now?
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 say, so give him a second to get there.
Deep
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's something you've worked hard to change about yourself?
Why ask it
A temper, a habit of going silent, always running late. Anyone can list flaws. You are listening for evidence that he noticed one and then did something about it.
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 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 do you call when something goes wrong, and why them?
Why ask it
If he has a person, you learn what he values in support: calm, jokes, practical help. If he says 'nobody, I just handle it', 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 fear has made more of your decisions than you'd like to admit?
Why ask it
Fear of looking stupid, of being broke, of turning into a particular relative. It is a heavy one, so offer your own answer first if he hesitates. That makes it a trade instead of a test.
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 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 the kindest thing anyone has ever done for you?
Why ask it
Hard to answer without going a little soft, which is the idea. It also shows you what registers as kindness to him: time, money, words, or someone simply turning up.
What would you try if you weren't worried about looking foolish?
Why ask it
Dancing, singing, a career change, saying something out loud. The thing he names is usually closer to a real wish than any answer to 'what are your goals'.
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 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 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.
How do you know when you really trust someone?
Why ask it
He will describe 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 the last photo you took that isn't of a person. What's the story?
Why ask it
Excluding people keeps it from feeling like a check of who he has been with. You will get a dog, a sunset, a receipt or a broken thing he meant to fix, and each one comes with an explanation.
What's the weirdest thing within arm's reach of you right now?
Why ask it
Answerable in ten seconds from wherever he is, which is what a text question should be. It also gives you a small, unposed look at his desk, car or nightstand.
What song is stuck in your head today, 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 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.
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.
What are you supposed to be doing right now instead of texting me?
Why ask it
Lightly flirty, since the polite answer is always 'something less interesting than you'. It also tells you whether to keep going or let him get back to the thing with the deadline.
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 your mood right now as a weather forecast?
Why ask it
Feelings are awkward to type and forecasts are not. 'Overcast with a chance of pizza' tells you to keep it light. 'Storm warning' tells you to ask what happened.
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 without turning it into an interview
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 side by side, not face to face
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 ways to use the list
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 question 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.