Random Questions to Ask a Guy
Random questions to ask a guy when there is a lull on a date, a quiet car or a text thread with nothing in it, and you want something you can say with no lead-in. The 102 questions are grouped in the order you would reach for them: Quick, This or that, Favorites, What if, About him and About us. The notes say why each one works out of nowhere, what to ask once he has answered, and which are better kept for a car, a text or a guy you already know.
Want questions from the whole vault instead? Try the random question generator.
The questions
Each question, and why to ask it
Quick
What's the last thing you looked up on your phone?
Why ask it
It needs no setup because the answer is sitting in his pocket, and it is nearly always something odd like an actor's age or how long to boil an egg. Ask what started the search, and that is where the story is.
What's the best thing you've eaten this week?
Why ask it
Food is the safest subject there is, and 'this week' keeps him from freezing up over an all-time favorite. It tends to end with a place you should try or a claim about his own cooking that you can ask him to back up.
If I handed you the speaker right now, what's the first song you'd put on?
Why ask it
In a quiet car you can make this literal and pass him the phone, unless he is the one driving, in which case he calls it out and you press play. The first pick is usually a safe one, so ask for the second, which is closer to what he plays when he is alone.
What's the weirdest thing you've seen this week?
Why ask it
Everyone has seen one strange thing by Wednesday: a dog in a stroller, a man carrying a door down the street. It hands him a small story to tell, and small stories are easier than opinions.
What's the last show you finished, and would you make me watch it?
Why ask it
He gets to recommend something, which is easier for a lot of guys than talking about themselves. If he says yes, ask how many episodes you have to give it before it gets good.
What's the most recent picture on your phone that you didn't take yourself?
Why ask it
It is nearly always a meme, a screenshot from a friend or a picture his mom sent of the dog. Asking for one he did not take gets you his group chats and his family in a single answer.
How many tabs do you have open right now, and what's the oldest one?
Why ask it
People are either at three tabs or three hundred, and both camps think the other is unwell. The oldest tab is the good part: a recipe from March, a jacket he never bought.
What word or phrase do you say way too much?
Why ask it
If you know him a little, you already have a guess, and telling him your guess is the fun of it. Expect him to catch himself saying it within the next ten minutes.
What's the best smell in the world, as far as you're concerned?
Why ask it
Cut grass, a bakery, gasoline, the inside of a new pair of sneakers. Nobody has a prepared answer, so you get to watch him think, and the smell he lands on comes with a place and a time that you can ask about.
What's the last thing you bought that you didn't need at all?
Why ask it
Impulse buys are more honest than planned ones: a third phone charger, a hat for a team he does not follow. Works well when you are walking past shops, and he will usually insist that he did need it.
Do you have a party trick, and when did it last come out?
Why ask it
Party tricks run small and odd: a wiggling ear, a coin caught off the elbow, the alphabet backward. In person he may simply do it, and if he swears he has none, ask what he tried to learn at twelve and gave up on.
What's the last compliment somebody gave you?
Why ask it
Sounds like a throwaway and lands warmer than he expects. Some guys struggle to remember one, and that is a natural opening to give him one yourself.
How old are the shoes you've got on right now?
Why ask it
Only works in person, where you can both look down. Guys tend to be either loyal to one battered pair or careful about a clean one, and each will explain himself at length.
What's the last thing you watched a how-to video for?
Why ask it
It shows what he has been trying to fix, cook or learn lately without asking about his hobbies outright. Find out if the video worked or if the thing is still broken.
What's the most recent thing you laughed at when nobody else was around?
Why ask it
A video, a group chat message, his own joke. It tells you what his sense of humor is like with no audience, and he may want to show you the thing itself.
This or that
Dogs or cats, and did you grow up with either one?
Why ask it
The oldest pick in the book, and still the quickest route to a pet's name and a story about it. A guy with no pets growing up usually has firm plans for the one he will get.
Sweet or salty when you're raiding the kitchen at midnight?
Why ask it
The midnight detail makes him picture his own cupboards, so you get a specific snack and not just a category. Good over text late in the evening, when he may be standing in the kitchen already.
Beach or mountains for a week off?
Why ask it
Underneath, you are asking whether his idea of rest is lying still or climbing something. Follow with the best trip of that kind he has taken.
Night owl or early bird, and is that by choice?
Why ask it
Many night owls are early birds against their will because of school or work, and they will tell you about it. Useful to know before you text him at 7 a.m. or at midnight.
Pancakes or waffles?
Why ask it
Two words, zero risk, and people defend their side harder than the subject deserves. If he says French toast, he is someone who looks for a third door, which is worth knowing.
Movie at home or movie at the theater?
Why ask it
Listen for what he mentions first: the pause button, the blanket, the size of the screen, the popcorn. Whichever side he gets animated about is an easy plan to suggest, if you are looking for one.
Driver or passenger on a long trip?
Why ask it
Best asked from one of those two seats. Drivers tend to like control and passengers like naps and snacks, and you learn right away whether the two of you would fight over the wheel.
Coffee, tea, an energy drink or nothing at all?
Why ask it
Four choices so nobody is left out, including the guy who runs on water and willpower. His exact order is worth remembering, because turning up with it later is an easy kindness.
Summer forever or winter forever?
Why ask it
'Forever' is what makes him think, since most people like the season they are not currently in. He will bargain for fall, and you can decide whether to allow it.
Big party or three friends on a couch?
Why ask it
Tells you how he recharges without using the words introvert or extrovert. Plenty of guys say 'depends who the three friends are', and then you get to hear about the friends.
Plan the whole trip, or figure it out when you land?
Why ask it
A travel question that is really about how he handles not knowing what comes next. Planners will describe a spreadsheet with pride, and everyone else will describe a night they had nowhere to sleep.
Fly or turn invisible?
Why ask it
Everybody has had an answer to this since they were seven, so he will not need a second. Picking is the easy half. Make him say what he would do with it on an ordinary Tuesday.
Outer space or the bottom of the ocean, if the trip were free and you were sure to get home?
Why ask it
Promising that he gets home removes the sensible objection, and what is left is which unknown pulls at him more. If he says ocean, a giant squid will come up within a sentence. Then ask whether he would still go if the trip took a year.
Windows down or air conditioning on?
Why ask it
Made for a quiet car, where you can settle it by pressing a button. It tends to slide into whose job the music is and how loud is too loud.
Rich and unknown, or famous and broke?
Why ask it
The money is the quick answer, so the fun is in a guy who hesitates. If he takes the fame, ask what he would want to be known for, and if he takes the money, ask what he would do all day.
Shower singer or shower thinker?
Why ask it
Silly enough to break a silence, and both answers go somewhere. Singers have a go-to song, and thinkers have a great idea they lost before they reached a towel.
Favorites
What movie could you watch for the tenth time and still not be bored?
Why ask it
Asking for the rewatchable one gets a truer answer than asking for his favorite, which people pick to sound smart. See if he can quote a line, because he almost certainly can.
What's your favorite pizza topping, and which one ruins the whole pizza?
Why ask it
The second half is the hook, since people are louder about what they hate. Practical too: you now know what to order and what to keep off his half.
What song, show or snack do you love and hope your friends never find out about?
Why ask it
The guilty pleasure question, offered three ways so he can choose the least incriminating. If he stalls, go first with yours, and keep his to yourself afterward, or it is the last one he will ever tell you.
What cereal was your favorite as a kid, and what took its place?
Why ask it
Childhood cereal comes with Saturday mornings, cartoons and rules about sugar attached. The replacement shows whether he grew out of it or simply buys his own box these days.
Which video game has eaten the most hours of your life?
Why ask it
If he plays, this will run for a while, so ask it when you have time to listen. If he does not, swap in a sport or a show, since the real question is what he sinks hours into.
What's your favorite day of the week if you're not allowed to say Friday or Saturday?
Why ask it
Taking away the easy answers makes him look at his real week. A guy who says Tuesday has a reason, like practice, a class he likes or a standing dinner, and that reason tells you about his routine.
What's your favorite thing to do when plans get canceled at the last minute?
Why ask it
Gets at what he does with free time he did not expect, which is closer to the truth than what he plans. Notice if he sounds relieved before he even answers.
What's your perfect sandwich, from the bread up?
Why ask it
'From the bread up' turns a one-word answer into a build, and he will have opinions about toasting. A good one for when you are both hungry and have not decided where to eat.
What's the best thing you've ever seen live, whether it was a concert, a game or anything else with a crowd?
Why ask it
Leaving it open means the sports guy and the music guy both have an answer. Ask who he went with and what the best single moment was, and you get the people in his life along with the event.
What's your favorite thing in your room?
Why ask it
He has to take a quick tour of his room in his head, and what he stops on is usually a gift, a trophy or something he built. Over text, a photo of it is a fair request.
What's your gas station order on a road trip?
Why ask it
Everyone has a fixed one and thinks theirs is normal. Next time you stop for gas, you can test whether he was telling the truth.
Which song do you know every word of, fast parts included?
Why ask it
The song is seldom a cool one, which is why it is a good question. If it comes on later, he owes you a performance, and he knows it the moment he answers.
What cartoon did you love when you were little, and does it still hold up?
Why ask it
Pins down which years he was a kid and what he hurried home to watch. Lots of people have rewatched an episode as an adult and have a verdict ready.
What's the best place you've ever been, and would you go back or leave it perfect?
Why ask it
Some guys would return every year and some would rather keep the memory untouched, which says a little about how he treats good things. If he would go back, ask what he would do exactly the same way.
What's the most comfortable thing you own?
Why ask it
A chair, a hoodie, a pair of ancient slippers. It is an easy one for a tired evening, and the follow-up is how long he has had it and who has tried to throw it out.
Which animal do you go to first at the zoo?
Why ask it
Nobody has to think hard, and grown men turn out to hold strong feelings about otters and big cats. If it comes up twice, a zoo or aquarium trip has just suggested itself.
What's your favorite sport to play, and is it different from your favorite to watch?
Why ask it
Plenty of guys play pickup basketball and watch something else entirely, and the mismatch is worth a question of its own. If he likes neither, ask what he does to burn off energy.
What if
If you could have any superpower, but only for ten minutes a day, which one would you take?
Why ask it
The time limit is what keeps this from being the question he has answered a hundred times. Ten minutes of flying is a commute and ten minutes of mind reading is trouble, so have him plan the ten minutes.
Someone hands you a million dollars that you have to spend by Friday. What's the first thing you buy?
Why ask it
The deadline rules out 'I'd invest it' and forces a real shopping list. Notice who else gets something, because a guy who buys his mom a house in the first three purchases is telling you plenty.
If you could time travel once, there and back, would you go to the past or the future?
Why ask it
Past people tend to be curious or nostalgic, and future people want to know how things turn out. Have him name the exact day he would set the dial to.
If you could have dinner with anyone, living or dead, who is it and what are the two of you eating?
Why ask it
A classic, and the menu is the fresh part: he has to picture sitting across from a hero while eating wings. Find out what his first question to them would be.
You're stuck on a desert island with one album, one snack and one person. What are your three?
Why ask it
Three small picks are easier than one big one, and he will agonize over the snack. Do not fish to be the person. Just enjoy his reasoning for whoever he names.
If you had to live as an animal for one week, which one are you choosing?
Why ask it
The week limit makes him practical about it, weighing naps against predators. House cat and eagle are the popular answers, and they come from two very different guys.
If you woke up amazing at one sport, which would it be and what would you do with it first?
Why ask it
Fans answer in a heartbeat and non-fans pick something unexpected like darts or surfing. The 'first' part separates the guy who would go pro from the one who only wants to beat his brother.
If you could spend a month inside any movie, show or game, which world would you pick?
Why ask it
Shows his taste without asking him to list favorites. Push on the details: where he would live there, what his job would be, and whether he would survive the month.
If aliens landed and gave you one afternoon to show them Earth, where would you take them?
Why ask it
A roundabout way of asking what he thinks is best about the world, and the answers are often very local: a taco truck, a certain lake. Then ask what he would steer them well away from.
You get a free plane ticket, but it leaves tonight. Where are you going?
Why ask it
Tonight removes the planning, so he names the place he has been quietly wanting to see. Ask what he would do in the first hour after landing.
If you could delete one chore from your life forever, which one goes?
Why ask it
Everybody has a nemesis, and it is usually dishes, laundry or anything involving a phone call. A relaxed way to learn what daily life looks like at his place.
If you could ask one question about your future and get a true answer, what would you ask?
Why ask it
Heavier than it sounds, so ask it once a couple of silly answers have already landed. What he asks about, whether work, family or where he ends up living, shows what is on his mind.
If you could invent a holiday, what would it be called and what would everybody have to do on it?
Why ask it
There is no stock answer to this one, so he has to build it from nothing: National Nap Day, or a day when nobody is allowed to reply 'k'. The rules he sets show what he wishes he had more of, and you can ask what date it falls on.
If you could bring back one thing that got discontinued, a snack, a show or a store, what would it be?
Why ask it
He will answer with real feeling, because everyone is still upset about one canceled show or vanished chip flavor. It also tells you what he grew up on.
If you had to change your first name tomorrow, what would you change it to?
Why ask it
Most guys have considered this at least once, often around age ten when they wanted to be called Blaze. Ask if he likes his real name and where it came from, which is a good story more often than you would expect.
If you had to teach a class tomorrow with zero preparation, what subject could you pull off?
Why ask it
A sideways route to what he knows cold, and it is rarely his job or his major. Ask for the first two minutes of the lesson.
In a zombie apocalypse, are you the leader, the one with the plan, or the first one caught?
Why ask it
Guys have usually thought this through in more detail than is healthy. Whatever role he claims, ask where he would hole up, and tell him honestly which role you think he would get.
If one song played every time you walked into a room, which song would you want?
Why ask it
He is choosing his own entrance, so the pick shows how he would like to come across: tough, funny or dramatic. Ask what would play if his friends were choosing instead.
A genie gives you three wishes, and none of them can be money. What do you ask for?
Why ask it
With money off the table he has to say what he would want the money for. The third wish is the telling one, since the first two go to the obvious things.
About him
What tiny thing annoys you way more than it should?
Why ask it
The pet peeve question, and people answer it with surprising energy: slow walkers, loud chewing, a phone on speaker in public. Remember the answer, mostly so you never do it.
What's the weirdest dream you can still describe from start to finish?
Why ask it
Dreams make no sense, so nobody can answer this one badly, and he will probably begin with 'okay, so I was at my old school, but it was also a boat'. Do not try to interpret it. Ask who else was in it and trade him one of yours.
If trophies were handed out for everyday stuff, what would you win one for?
Why ask it
It lets him brag about something small, like parallel parking or never losing his keys. Guys who are shy about real achievements will happily claim best sandwich maker.
What's a hill you'll die on that doesn't matter at all?
Why ask it
This is where you find out that he has rules about loading a dishwasher or which way the toilet paper hangs. Disagree with him on purpose and enjoy the next five minutes.
What do you refuse to lose at, even when nothing is riding on it?
Why ask it
Board games, finding the best parking spot, getting off the plane first. Guys who call themselves laid-back still have one, and finding out early saves you from challenging him to it by accident.
What job did you think was the coolest in the world when you were little?
Why ask it
Sounds like trivia and turns out to be a picture of him at seven, wanting to drive a garbage truck or play in the pros. Ask what part of that job he would still enjoy.
What was your first username or email address, and how embarrassing is it now?
Why ask it
Embarrassing in the safest possible way, since he was eleven and thought 'xX_shadow_Xx' was a strong choice. The name tends to point at whatever he was obsessed with that year, so ask about that next.
Were you a loud kid, a quiet kid or a kid who was always in trouble?
Why ask it
Three boxes make it quick, and he will probably ask for a fourth. Ask whether he is still that kid, and whether his mom would agree with his answer.
What did you believe for way too long as a kid?
Why ask it
That swallowed gum stays in you for seven years, that his teacher lived at the school, that the moon was following the car. Funny first, and then you hear who finally told him.
Spiders, heights or speaking in front of a crowd: which would you pay the most to avoid?
Why ask it
Three ordinary fears, so naming one costs him nothing and no one has to confess anything deep. Say which one you would pay to skip, then ask how much money would get him to face his.
Do you believe in ghosts, aliens, luck or none of the above?
Why ask it
Four doors in one question, and he only needs to open one. A flat 'none' is rare, and most people have a single story they cannot explain, so ask for that story.
Who's the funniest person you know, and what makes them so funny?
Why ask it
Asking about someone else takes the pressure off, and he will act out the friend's best line. You also find out who he spends his time with.
What would your friends say is the most 'you' thing you do?
Why ask it
Putting it in his friends' mouths lets him describe himself without sounding full of himself. Once you meet them, you can check his answer against theirs.
What do you spend money on without thinking, and what do you refuse to pay for?
Why ask it
Shows where his priorities sit without asking about money directly: some guys buy concert tickets freely and will circle for twenty minutes to avoid paying for parking. He will get more worked up about the second half.
What's the best gift anyone has ever given you?
Why ask it
What he names is seldom the priciest thing he owns. Listen for who gave it, because you are hearing about someone who knows him well and what being known looks like to him.
What's the nicest thing a stranger has ever done for you?
Why ask it
He may need a minute, so leave room for it. The story shows what kindness looks like to him, and a good second question is whether he has ever done the same for someone else.
What's the earliest thing you can remember?
Why ask it
It comes out in fragments: a kitchen floor, a dog, a red coat. Nobody has a rehearsed answer, which is why it works with no lead-in, and it usually opens onto where he grew up and who was around.
What have you changed your mind about lately?
Why ask it
It can be as small as mushrooms or a band he used to make fun of. If he names one without squirming, you have also learned that he can say 'I was wrong' out loud.
What's one thing you want to have done by this time next year?
Why ask it
A year is close enough that he will name something real, like a trip, a team or a car, where 'bucket list' gets you skydiving. Ask what the first step is and whether he has taken it.
About us
If I were a snack in a vending machine, which one would I be?
Why ask it
Ridiculous enough that he cannot get it wrong, and yet whatever he picks is a tiny description of you. Make him explain the choice, then tell him which snack he is.
If we got in the car right now with no destination, which direction would you drive?
Why ask it
Especially good if you are in the car already. He will name a road, a town or 'toward food', and sometimes the answer turns into the actual plan for the afternoon.
If we found a dog today and kept it, what would we name it?
Why ask it
Pure play, and it shows how the two of you negotiate: he suggests, you veto, somebody proposes Kevin. Works at any stage, since a made-up dog commits nobody to anything.
What's one food I have to try because you love it?
Why ask it
He gets to be the expert, and you get a ready-made thing to do together if you want one. Promise an honest review, including if it is bad.
What show should we start together, and are you the type to watch ahead?
Why ask it
Watching ahead is a small betrayal that people take very seriously, which is why the second half gets a bigger reaction than the first. Settle the rules now, before either of you has something to confess.
Who would get us lost faster, you or me?
Why ask it
Directions are a touchy subject for plenty of guys, and that is what makes it funny. Expect a defense of his sense of direction and at least one story about a missed exit, and have your own ready.
Which of us would crack first in a week with no phone?
Why ask it
Expect him to say you, at which point you can ask how he coped the last time his battery died. The teasing stays friendly because neither of you would last, and it can turn into a real bet for a single evening.
What do you think I'm secretly good at?
Why ask it
A guessing game that doubles as a compliment, since he has to imagine you being skilled at something. Tell him how close he got, and then guess his.
Guess three things about me that you don't know yet, and I'll tell you how many you got.
Why ask it
Turns the usual direction around so that he is the one working. His guesses show how he sees you so far, and the wrong ones are the ones you will both remember.
If I ordered for you at a restaurant, what do you think I'd get you?
Why ask it
He is being asked how well he thinks you know him. Tell him your real guess afterward, and next time you eat out, one of you can try it for real.
If we had to make dinner with only what's in your kitchen right now, what are we eating?
Why ask it
A fridge inventory with a plot. Cereal and hot sauce is a common and honest answer, and it tends to end with a debate over who is the better cook.
If we entered a contest as a team, what kind of contest could we win?
Why ask it
It asks what the two of you are good at together, wrapped up as a joke about chili cook-offs and three-legged races. He will also end up saying which of you would carry the team.
If we swapped lives for a day, what's the first thing you'd do as me?
Why ask it
He has to describe your life as he pictures it, and the picture is often funnier and kinder than you expect. Then tell him what you would do with a day as him.
What's something random you've always wondered about me?
Why ask it
Gives him permission to ask the thing he has been curious about, which is usually smaller than you would fear: your middle name, why you hate a certain song. Answer it properly, since you asked for it.
What do you remember about the first time we talked?
Why ask it
Details are the prize here: what you were wearing, what you said, where he was standing. If he remembers nothing, laugh and give him your version, which is its own good conversation.
What's the most random thing you remember me saying?
Why ask it
Flattering to ask and flattering to answer, because a quote from weeks ago shows he was listening. Be ready for a line you have no memory of saying.
How to ask a random question and get more than a shrug
Practical guidance for the conversation itself
Dropping a question into a silence
Say it like you just thought of it
A random question works because it sounds like something that crossed your mind, so skip the windup. 'Okay, pancakes or waffles?' in a quiet car is enough. Explaining that you found a list of questions makes him feel he is being run through it.
Give your own answer second, and quickly
Let him go first, then give yours without being asked. A guy who has just admitted to 214 open tabs wants to hear your number, and once you have both answered it is a conversation and no longer a quiz.
Chase the detail before the next question
The oldest tab, the person who gave him the gift, the reason he needed to know how long to boil an egg: the second thing he says is nearly always better than the first. One 'wait, why?' does more than three fresh questions.
Two or three, then let it run
If a question turns into ten minutes about his brother's terrible driving, it has done its job. Leave the rest of the list alone until the talk runs dry by itself.
Four lulls and what to reach for
A pause on a date
Use This or that and Favorites. They are short enough to answer between bites and they give you plenty to react to. Keep About us for later in the evening, when it is clear you are both enjoying yourselves.
A quiet car
Pick the ones you can act on: the speaker, windows down or air conditioning, the gas station order, which direction he would drive. If he is at the wheel, you work the phone and the buttons. What if questions suit a long stretch of highway, because he can think with his eyes on the road and nobody has to hold eye contact.
A text thread with nothing in it
Send one question with no greeting and no 'so'. Quick questions suit a phone best, since the answer is often on the phone already: the last search, the oldest open tab, a picture somebody sent him. Add your own answer in the same message so he has something to reply to even when he is busy.
A boy you hardly know
With a classmate or a friend of a friend, stay in Quick, This or that and Favorites. They ask for nothing personal and work in a hallway or a group chat. About him can wait until he has started asking you things back.
What each group is for
Quick and This or that cost him nothing
These can be answered in a word, which is exactly what you want when a silence has gone on too long. Their job is to get him talking at all. If a pick starts an argument about waffles, stay in the argument.
Favorites and What if give him room
Once he is answering in sentences, move to these. Each has a twist built in, a ruined pizza or a superpower with a time limit, so he cannot hand you the answer he has given a dozen times before.
About him only sounds random
Questions about childhood beliefs and pointless hills to die on feel as light as the rest, but the answers tell you what he was like at seven and what he cares about now. Mix one in after every few silly ones and do not announce the change of gear.
About us needs some history
The first few are pure play, such as the vending machine snack or the dog's name, and work on a guy you met last week. The ones further down, like the first time you talked or something he remembers you saying, assume the two of you have a past to draw on. If he answers one warmly, that is a fair sign he would like more of them.
When a question falls flat
He answers in one word
Take the word and build on it yourself: 'Waffles? Okay, toppings.' If two in a row get nothing, he may be tired, driving or thinking about something else, and a comfortable silence is a better choice than a third question.
He says 'I don't know'
Offer your own answer or give him two options to choose between. 'I don't know' usually means the question was too wide open, and a wrong guess from you ('I bet it's a hoodie') is easier to correct than a blank is to fill.
The answer turns crude or unkind
Skip the polite laugh. Change the subject with a pick from This or that, 'okay, windows down or air conditioning?', and carry on as if nothing was said. If it keeps happening, that is information about him and no fault of the questions.
A light question hits something real
The earliest memory or the best gift can lead to a parent who is gone or a rough year. Listen, say you are glad he told you, and let him decide whether to stay there. Following a real answer with a joke question right away can feel as if you were not listening.