Questions to Ask Your Guy Friend
Questions to ask your guy friend when it's just the two of you and you want to know him better than the jokes let on. They're written for a friend, not a crush, and they run the way the conversation tends to go: funny and random ones first, then getting past the banter, the guy's point of view, deep ones, questions about the friendship itself and a last group that works over text. Each has a note on what a good or a worrying answer sounds like, or what to do with what he says.
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The questions
Each question, and why to ask it
Funny
What's the dumbest thing you and your friends have argued about for over an hour?
Why ask it
A good answer comes with a full reenactment and a ruling on who was right. If he claims they never argue, ask whether a hot dog is a sandwich and time how long his calm lasts.
What hill will you die on that matters to absolutely nobody else?
Why ask it
Whether it's cereal before milk or the only correct way to load a dishwasher, take the other side for two minutes even if you agree with him. The defense is funnier than the opinion, and you'll hear it again every time the subject comes up.
What's the stupidest way you've ever hurt yourself?
Why ask it
The story usually starts with a dare or a bike and gets better at the part where he tried to walk it off. Ask whether there's a scar and who was standing there laughing. If it ended at the emergency room, let him decide how funny it is.
If you got a walk-up song every time you entered a room, what would it be?
Why ask it
He will either answer in one second or need the rest of the day, and both are entertaining. Give him yours, then assign songs to the people you both know.
What movie do you claim not to like but would watch again tonight?
Why ask it
The honest answer is often an animated movie or a romantic comedy he knows by heart. Owning up fast means he's fine being laughed at, a good sign for anything more personal you ask him later. A guy who swears there isn't one should have to sit through your guesses until he cracks.
What's the worst meal you've made for yourself and eaten anyway?
Why ask it
It's a small look at how he lives when nobody is watching: dry cereal for dinner, noodles made with a kettle, a sandwich with one ingredient. Trade your own low point so it stays a joke and not an inspection.
What did you look up at 2 a.m. that you had no reason to need to know?
Why ask it
Whatever he names, whether penguins have knees or how deep the ocean goes, is where his brain wanders when it's left alone. Make him tell you the answer he found, then admit your own last pointless search.
If I handed you fifty dollars and one hour, what would you come back with?
Why ask it
Some guys return with one carefully chosen thing and some with a bag of snacks and no change. Either way you learn how he spends, and the answer doubles as a gift idea for his birthday.
What's the most trouble you've ever been in that you still say was worth it?
Why ask it
The 'worth it' half is the real question, because it tells you what he'd take the punishment for twice. Ask who caught him and what the sentence was. Keep it for detention-level stories, and leave it out with a friend whose trouble has been the serious kind.
Past the banter
What were you like at twelve, and would the two of us have been friends then?
Why ask it
A soft way into his past, because he gets to describe a kid instead of himself. Notice whether he talks about that kid kindly. Then answer the second half honestly, which often means admitting you'd have ignored each other.
Is there anyone you like right now, and do you want my help or should I stay out of it?
Why ask it
The second half is what makes it a friend's question: he can say a name without signing up for a matchmaking campaign. A fast 'no' with a grin often means yes, so leave the door open and don't fire guesses at him. Whatever he tells you goes no further, least of all to that person's friends.
What are you into that you rarely bring up because you figure nobody wants to hear it?
Why ask it
Give him a full five minutes on it and ask at least two real questions. If he keeps checking whether he's boring you, that tells you how the last person reacted. Bring it up again next week and he'll know you meant it.
What's your family like at home when nobody's over?
Why ask it
You're asking for the unedited house, whether that's loud, silent or dinner in front of the TV in separate rooms. A short answer or a quick change of subject can mean home is complicated right now. That's his to open, so leave it.
What did you want to be before people started asking what your plan was?
Why ask it
The early answer, pilot or game designer or the person who drives the Zamboni, often still has a real wish inside it. Ask what he liked about the idea, and whether anything in his life now gives him the same feeling.
What did you used to do all the time and then drop, and do you miss it?
Why ask it
When he lights up describing it, ask what it would take to start again and offer to come along the first time. 'I wasn't good enough' deserves a gentle 'says who?'
What's been stressing you out lately that you've been playing down?
Why ask it
Ask it somewhere side by side, in a car or on a walk, where he doesn't have to look at you. 'Nothing, I'm good' on the first try is normal. Say 'okay, the offer stands' and he may come back to it an hour later.
What are you quietly proud of that never comes up when we're joking around?
Why ask it
Friendships built on teasing don't leave much room to say something went well. Whatever he names, skip the joke this once and say plainly that it's impressive. He'll probably wave it off, and he'll remember that you said it.
Who do you go to when something is wrong?
Why ask it
A named person, a brother or one old friend, is the answer you're hoping for. 'I just deal with it' is worth noticing. You don't need to fix that today, only to say that you're an option.
Which version of you do most people get: the one from the group, or the one I'm talking to now?
Why ask it
He may say they're the same guy, and for some people that's true. If he admits the group gets the louder one, ask which is less tiring to be. Hearing that you get the other one is a compliment, so take it as one.
Guy's view
What's the weirdest thing you believed about girls when you were ten?
Why ask it
An easy first question about how guys see girls, because the joke is on a ten-year-old and not on him. Trade what you believed about boys at the same age and see who was further off.
Do you think a guy and a girl can be just friends, or does one of them always end up wanting more?
Why ask it
He knows he's sitting next to the evidence, so the first reply will be 'obviously, look at us' or a joke. The interesting part is the exceptions: the friendships he has watched get complicated, and what he thinks went wrong. Give your own view as well, so it's a debate and not a test.
What do girls stress about that guys honestly don't notice?
Why ask it
Chipped nails and a repeated outfit tend to top his list of things he has never once registered. Ask what he does notice, which is more often whether someone seems glad to see him. Then turn it around and ask what guys worry about that girls never see.
What do guys talk about when it's only guys in the room?
Why ask it
Prepare to be underwhelmed if the honest answer is a game, food and an argument about nothing. The follow-up that matters is how long it takes before anyone asks how someone is really doing.
When a guy takes a whole day to text back, what's going on, in your experience?
Why ask it
You're getting one guy's read, so treat it as a single opinion and not a rule. A friend who says 'sometimes he's busy and sometimes he isn't that interested' is being more useful than one who only reassures you.
How can you tell one of your friends likes someone before he has said anything?
Why ask it
He'll describe the tells he has seen: a name that keeps coming up, a sudden new hobby, a guy who starts caring about his hair. It's funny on its own, and handy the next time you're trying to read someone.
When a guy says 'I'm fine', what can it mean, and which meaning do you use most?
Why ask it
Have him list them, since there are probably at least three: fine, tired, and not ready to talk. Then ask how you'd tell his versions apart. That's information you'll want on a day when he isn't joking.
What do guys tell each other after a breakup, and does any of it help?
Why ask it
You may hear that the advice is mostly 'you're better off' and an invitation to play something. Ask what he would have wanted to hear instead. It tells you what to say to him when it's his turn.
Do guys compliment each other, and what's the nicest thing a guy friend has said to you?
Why ask it
If he has to think back a long way, that's the answer. Notice whether the compliment he remembers was about something he did or something he is. Then pay him a specific one yourself and enjoy how badly he takes it.
What do guys get teased for by other guys that you think is unfair?
Why ask it
The honest answers are things he does himself, like ordering the sweet drink or being close to his mom. 'It's all harmless' is a common first reply, so ask whether he has ever changed what he ordered, wore or said because of it.
If I liked a guy, what would make you tell me 'not him'?
Why ask it
His list comes from seeing how guys act when no girls are around, a view you can't get yourself. Specifics like 'how he talks about his ex' or 'how he treats the quiet kid' are worth remembering. 'Nobody's good enough' is sweet and no help, so push for a real one.
What have you always wanted to ask a girl but figured it would come out wrong?
Why ask it
Turnabout is fair when you've been quizzing him about guys. Answer plainly, and say 'that's just me, not all girls' where it applies. If the question is one you'd rather not take, say so without making him feel bad for asking.
Deep
Who is a man you'd like to turn out like, and what is it about him?
Why ask it
Pay attention to the quality more than the person. Patience, or the way an uncle treats waiters: whatever he picks is what he's measuring himself against. If you already see some of it in him, say where.
What are you afraid of that has nothing to do with spiders or heights?
Why ask it
Ruling out spiders and heights shuts the easy exit, and what comes next is more like ending up stuck or letting a parent down. Don't rush to tell him it won't happen. 'That makes sense' does more.
When do you feel most like you're faking it?
Why ask it
He might say at work, in class, or whenever someone asks about his plans. You have a place like this too, so offer yours right after his. If his answer is 'most of the time', slow down and ask what a day without faking would look like.
What do you compare yourself to other guys on, even though you know better?
Why ask it
The first reply is often a laugh. Once he names it, height or money or how easily another guy talks to people, don't argue him out of it on the spot. Ask who he has in mind, because it's often one particular person.
What would you change about how you and your dad talk to each other?
Why ask it
Swap in whoever raised him if you know his family. 'We only talk about sports' and 'we don't, really' are heavy sentences said lightly, so let them sit a second before you reply. Leave the question out completely if that relationship is raw or the person is gone, unless he brings it up himself.
What are you putting off deciding?
Why ask it
It might be a course, a move, or whether to say something to someone. Hold your opinion for now and ask what he'd choose if he had to decide by Friday. A quick answer often means he already knows and is waiting for someone to say it's allowed.
When did you last feel that somebody really got you?
Why ask it
A recent, specific moment is a good sign that he has people. A long pause, or an answer from years back, may mean he has been getting by on jokes for a while. You don't have to say anything wise. Staying in the conversation is the reply.
What apology do you still owe someone?
Why ask it
He will know right away who it is, even if he takes a while to say it. Ask what has stopped him, and don't assign homework. If the someone turns out to be you, hear it out before you say it's fine.
What's the hardest thing you've been through that most people around you don't know about?
Why ask it
Only for a night with time and privacy, and never as a way to prove how close you are. He can answer in one sentence or pass, and both are fine. Thank him and keep it to yourself. If it sounds like more than a friend can carry, encourage him to talk to someone he trusts who can help.
About us
What was your honest read on me the first week we knew each other?
Why ask it
Expect 'loud', 'scary' or 'I thought you hated me', delivered with too much enjoyment. Trade yours. Two wrong first impressions are a nice reminder that this friendship wasn't obvious and you both built it.
How is being friends with me different from being friends with the guys?
Why ask it
Good answers are concrete: you ask follow-up questions, you remember birthdays, you don't let him change the subject. If all he comes up with is 'you smell better', laugh and ask again. Tell him what you get from him that your other friends don't give you.
What do you tell me that you wouldn't tell your guy friends?
Why ask it
The answer shows what your place in his life is: family things, worries, or the stuff he's excited about and embarrassed by. 'Nothing, really' isn't a verdict on you. More likely the two of you have mostly joked so far.
When people assume we're more than friends, what do you say?
Why ask it
Compare your stock answers, because you've both been asked. An eye-roll and a practiced line suggest it's simple for him. Agreeing on what you both say helps later, when one of you is seeing someone who wonders about it.
If one of us starts dating someone, what do you want to stay the same between us?
Why ask it
Easier to settle now than in the first month of somebody's new relationship. Listen for specifics: the Sunday call, the dumb messages, being able to hang out one on one. Say what you'd want too, and what you'd adjust so a partner feels comfortable.
What do I do that annoys you that you've been too nice to mention?
Why ask it
Promise not to argue before he answers, and keep the promise even when it turns out to be your habit of showing up late. 'Nothing' is him being polite. Name one thing you know you do and ask whether it made the list.
Would you tell me if you thought I was making a bad call, or would you let me find out?
Why ask it
You're asking what kind of honesty you can count on. 'I'd tell you once and then drop it' is about as good as it gets. If he admits he'd stay quiet, tell him he has permission, and be specific about how you'd want to hear it.
When you disappear for a few days, do you want me to chase you or give you room?
Why ask it
Quiet because things are bad and quiet because things are busy look the same from the outside. Get an actual instruction, like 'one text, then leave it' or 'call me'. Then give him yours, since you probably have your own version of going missing.
When did I help you without knowing it?
Why ask it
Save it for the end of a good conversation, because it's the warmest thing you can ask him. The answer is usually small, a ride or a message that arrived on a bad day, and you may not remember it. Have one ready about him.
Over text
What are you eating right now, and should I be worried?
Why ask it
A zero-effort text that tends to get a photo back, so use it to restart a chat that has gone a week without a message. A proper meal earns respect, and a spoon in a peanut butter jar earns follow-up questions.
What's the last thing that made you laugh at your phone? Send it.
Why ask it
He sends a video or a screenshot and you learn what his sense of humor does unsupervised. Reply with something of your own and not only 'lol'. A trade of dumb clips keeps a friendship going between hangouts.
Describe your mood right now using only a movie title.
Why ask it
A guy who would never type 'kind of down today' may happily send the name of a disaster film. Play along with your own title first. If his is darker than the joke needs, drop the game and ask what's up.
What's the third song on your most-played list? No swapping.
Why ask it
The 'no swapping' rule is the fun, since number three is rarely the one he'd choose to show off. Listen to it and report back. A screenshot as proof is fair to demand if the answer sounds too cool.
What happened today that you'd have told me about if I'd been there?
Why ask it
It turns 'how was your day' into a request for one small story: the teacher's meltdown, the near miss in the parking lot, the dog he met. On a day when he answers 'nothing really', send yours and leave it there.
You get to keep one forever: pizza, burgers or tacos. Which, and can you defend it in one message?
Why ask it
Good for a slow afternoon, because he can answer in four words or forty. Disagree on principle. Whoever loses the argument buys the winner's choice next time you hang out, which turns a text into a plan.
I need a guy's opinion and you have ten seconds: the first one or the second?
Why ask it
Send two photos with it: shoes, a gift for your brother, two haircuts. The time limit stops him from overthinking and gets his gut answer. If all he says is 'both are fine', ask which one he'd notice.
You've been quiet this week: busy, tired or something else?
Why ask it
Three options let him answer with one word, which is all some days allow. 'Busy' and 'tired' need nothing more than 'got it, I'm around'. 'Something else' is an opening, so ask whether he'd like to talk or be distracted.
How to ask a guy friend without making it weird
Practical guidance for the conversation itself
Picking the moment
Ask while you're doing something
These land better side by side than face to face: in a car, on a walk, over food, in the middle of a game. Having something to look at takes the pressure off, and a pause reads as thinking instead of as an awkward silence.
One to one, not in front of the group
The list is written for two people. With his friends around he has a part to play, and most of Past the banter and all of Deep will get the group version of him. Save those for a time when nobody else is listening.
Follow the order of the groups
Funny comes first because laughing together is what earns the next question. Past the banter and Guy's view fit the middle of a hangout. Deep needs time and nowhere to be. About us works best near the end, when you've both already said a few true things.
Three or four, not the whole page
Read through, choose the handful you honestly want his answer to, and let the conversation go wherever his answers take it. Working down a list turns a friend into an interview subject, and he will start answering like one.
Keeping it a friend's question
Say why you're asking
'I found a list and some of these are good' is enough of a reason. A deep question dropped in with no frame can read as flirting or as an intervention, and one sentence of setup removes both readings.
Answer everything you ask
Go second on the funny ones and first on the hard ones. If you ask what he's afraid of, have your own answer ready and give it at the same depth. A trade feels like friendship. Questions that only go one way feel like research.
One guy is not all guys
The Guy's view questions get you his view, shaped by his friends, his family and his age. It's worth having, and it isn't a ruling on what some other guy meant by a late reply. Use what he says to think with, then ask the person involved.
Be honest with yourself about the dating ones
Asking whether a guy and a girl can be just friends, or what happens when one of you dates someone, assumes 'just friends' is the true answer for both of you. If it isn't true for you, he thinks he's in a different conversation from the one you're having. Sort out what you want before you ask.
If you're a guy asking a guy
Guy's view is written for a girl asking, so skip it or flip the questions into 'is that true of us?' Everything else works as it stands, and Past the banter matters more, because two guys can go years on jokes alone.
What to do with what he says
When he jokes his way out
Let the joke land, laugh, then ask once more in plain words: 'okay, but really?' If the second try gets another joke, that's a no for today. Move on without comment and he'll trust the next question more.
When he says something heavy
Resist the urge to fix it. 'Thanks for telling me' and 'do you want advice or do you just want to say it' cover most situations. If what he tells you makes you worried about his safety, don't hold it alone: bring in someone you trust, an adult if you're both still in school, or help him get to someone who can help.
What stays between you
Anything from Past the banter or Deep stays out of the group chat, including as a joke and including a screenshot sent to one person. He told one friend. If it travels, he will go back to answering everything with a bit.
When he turns the question on you
That's the conversation working. Answer it properly instead of steering back to your list, and if he asks something that isn't on this page, follow that instead.
Using them over text
Which ones travel
The Over text group was written for a phone, and most of Funny works there too. Guy's view does fine in a slow back-and-forth. Keep Deep and the harder About us questions for in person, where he can hear that you're asking kindly.
Give a slow reply room
Send one question and wait. A reply that takes hours isn't an answer about the friendship, and a second message chasing the first makes a light question feel like a demand. If it sits for a couple of days, send something easy instead of asking whether he saw it.
Turn a text into a plan
The best thing a text thread can do is end in a hangout. When a question gets him going, the food debate or the song or the thing he used to do, say 'tell me the rest on Saturday' and pick a place.