21 Questions to Ask a Guy
Questions for playing 21 Questions with a guy you like, in person or over text, whether he is someone you have been talking to for a while or a boy at school you barely know. The page holds four rounds of 21, each a full game on its own: Easy for someone you have just met, then Funny, Flirty and Deep for when you know each other. You take turns, he can throw any question back at you, and every question carries a note on what his answer tends to show or when to hold it back.
One at a time · 01 of 84
Easy
“What's your favorite movie of all time, and how many times have you seen it?”
Why ask it
The standard opener, because he cannot get it wrong. Listen to the count more than the title: someone who has watched a movie a dozen times will tell you why without being asked, and that is your follow-up handled.
Want questions from the whole vault instead? Try the random question generator.
The questions
Each question, and why to ask it
Easy
What's your favorite movie of all time, and how many times have you seen it?
Why ask it
The standard opener, because he cannot get it wrong. Listen to the count more than the title: someone who has watched a movie a dozen times will tell you why without being asked, and that is your follow-up handled.
Which band or artist would you go see live no matter what the ticket cost?
Why ask it
Asking about a concert gets a real name where 'what music do you like' gets 'a bit of everything'. If you know the artist, say so. If you don't, ask which song to start with and actually play it later.
If you had two free weeks, a car and a full tank, where would you head?
Why ask it
A road trip shows more than a dream destination does: whether he plans every stop or just goes, and who gets the passenger seat. Ask what would be playing in the car.
Back in elementary school, what were you sure you'd grow up to be?
Why ask it
A firefighter, a pro athlete, the driver of the garbage truck. Nobody is embarrassed by a plan made in second grade, so it is safe on the first day you talk. Ask what happened to the plan only if he seems to want to say.
What does someone in your family cook that nothing else comes close to?
Why ask it
Home cooking comes with a person attached: a mom, a grandparent, an uncle at a grill. You hear a little about his family without asking about it directly. Remember the dish, because knowing it a month from now will count for more than it should.
What do you do for fun on a weekend: sleep, sports, friends or a screen?
Why ask it
Offering the menu makes it quick to answer over text. Whatever he picks first is what he protects his time for, and it tells you what a weekend plan with him would realistically involve.
What could you talk about for an hour without running out of things to say?
Why ask it
Then let him, at least for a few minutes. How a guy sounds when he is on his subject is one of the better things you can learn in a first game, and he will remember that you listened.
Are you a dog person, a cat person, or something stranger?
Why ask it
Anyone with a pet will have a photo out within ten seconds, and you should ask to see it. If he has none, ask what he would get. In person this fills a quiet moment better than almost anything.
What's the best vacation you've been on so far, and who was there?
Why ask it
'Who was there' matters more than the place. A family road trip, a week with his friends and a trip alone are three different stories, and you hear who he likes spending long days with.
If you could have dinner with anyone at all, famous or not, living or not, who would you invite?
Why ask it
An athlete or a musician is the usual pick, and it hands you his hero in one word. Now and then the answer is a grandparent he barely knew, and that one deserves a gentler follow-up than 'why them?'. Either way, ask what he would want to ask them.
Which class do you actually like, or liked best back in school?
Why ask it
Works whether he is still in school or finished years ago. Skip the follow-up about grades and ask about the teacher: a favorite class nearly always turns out to be a favorite teacher.
What show would you make me watch first if you got to pick?
Why ask it
He is recommending, so he will sell it, and you hear what he finds funny or gripping. If you have seen it, that is ten minutes of conversation for free. If not, promise one episode and a report, which gives you a reason to talk again.
Who in your family are you most like, and would they agree?
Why ask it
Family questions can get heavy, but this one stays light, and you find out who is in the family without asking for a list. Listen for whether he says the name proudly or with an eye roll.
What sport or game are you honestly good at?
Why ask it
'Honestly' gives him permission to brag a little, which most guys enjoy and few get invited to do. If it is something two people can play, you have just found the first thing to do together.
What do you want to try at least once, even if you'd be terrible at it?
Why ask it
'Even if you'd be terrible' takes away the pressure to sound impressive, so you get surfing, stand-up or a cooking class. Ask what has stopped him so far. If it is something you want to try too, say so.
Are you a morning person or a night owl, and when would you get up if nobody made you?
Why ask it
Noon is a common and honest answer. It is practical if you end up texting, too: you learn when he is awake enough to reply, and when a slow answer means he is asleep and nothing else.
Sweet or salty: which snack can you not be trusted around?
Why ask it
About as low stakes as a question gets, which is why it suits someone you met an hour ago. Expect a brand name and strong feelings. Disagreeing with his pick is a perfectly good way to start teasing him.
What's the best present anyone has ever given you?
Why ask it
He will describe the gift, but the part worth hearing is who gave it and why it landed. Something handmade or chosen with care usually comes with a story about the person, and that story is more use to you than a wish list.
What did you do all summer as a kid once school let out?
Why ask it
Bikes, a pool, a grandparent's house, video games in a dark room. You get his childhood in one picture without asking anything personal, and he will usually ask for yours right back.
How would your best friend describe you in one sentence?
Why ask it
Easier than asking him to describe himself, because he can hide behind the friend. Notice whether the sentence is a joke or a compliment. Expecting to be roasted is a good sign: it usually means he is at ease with himself.
What's coming up in the next few weeks that you can't wait for?
Why ask it
Shows you what his life is busy with right now: a game, a trip, a birthday, the end of exams. If he says 'nothing really', suggest something. That is as close to an opening as an easy question hands you.
Funny
Which superpower would you pick: flying, invisibility, reading minds or something better?
Why ask it
Everyone has thought about this, so nobody stalls. Make him defend the choice and then tell him what is wrong with it. A guy who picks mind reading should be asked whose mind he wants to read first.
What's the most embarrassing thing that's happened to you in front of a crowd?
Why ask it
Give yours first if he hesitates, because nobody wants to be the only one who confessed. If he can tell it and laugh, he does not take himself too seriously, which is worth finding out early.
You come into a fortune overnight. What's the dumbest thing you buy in the first week?
Why ask it
'Dumbest' stops him from saying he would invest it. You get the jet ski or the lifetime supply of something, and usually, a sentence later, the house he would buy his mom.
What three things are you taking to a desert island, and why isn't one of them a boat?
Why ask it
The old standby with the loophole closed. Practical guys pack a knife and a water filter, funny guys pack a couch. Ask whether you would make the list as a fourth item and see how fast he answers.
What tiny thing do other people do that drives you up the wall?
Why ask it
Let him rant, since anyone fully worked up about people who stop at the top of an escalator is good entertainment. Then give him yours, and see whether the two of you can agree on a shared enemy.
What's a hidden talent of yours that hardly anyone has seen?
Why ask it
Ear wiggling, a card trick, an accent, free throws with the wrong hand. In person he will usually start showing you before you finish asking. Over text, a ten-second video is the only acceptable proof.
Do you have a scar with a good story, or a bone you broke doing something dumb?
Why ask it
Nearly every guy has one, and most are proud of it. Ask to see the scar if there is one. 'And did you do it again?' gets a yes more often than you would think.
What's the biggest animal you honestly think you could outrun?
Why ask it
Guys have usually thought about this more than they will admit, and the confidence is the joke. Look doubtful whatever he names. Asking for his reasoning gets you a five-minute speech with hand gestures.
If you had to sing one song in front of everyone you know, which gives you the best chance?
Why ask it
Even a guy who would never touch a microphone has picked one in his head. Ask for a few lines if you are together. Over text, ask for a voice note and find out how brave he is.
What lie did an older kid tell you that you believed for years?
Why ask it
That swallowed gum stays in you for seven years, that the ice cream truck plays music only when it has run out. Sweet as well as funny, so a nice one for a guy who is a little shy. Ask how he found out the truth.
If your friends had to cast you as a cartoon character, who would they pick?
Why ask it
Asking for his friends' pick keeps him honest. Left to himself he would say the hero, and they would say the sidekick who eats everything. He is going to ask who you would be, so have a pick ready that is not the obvious one.
What's the worst thing you've ever cooked, and who had to eat it?
Why ask it
A kitchen disaster is easy to laugh about and tells you, on the side, whether he cooks at all. Anyone who claims never to have ruined a meal has probably never made one.
Would you rather always be ten minutes late or always be twenty minutes early?
Why ask it
A would-you-rather that is really about him. He already knows which one he is, and so does everyone who has waited for him. Handy to know before the two of you ever agree on a time to meet.
What's the funniest thing you ever got in trouble for?
Why ask it
School stories work best, and if you know him from class you may even have been in the room. Listen for whether he was the ringleader or the one caught holding the evidence.
Have you ever sent a message to exactly the wrong person? What did it say?
Why ask it
Made for playing over text, where the danger is live. The stories about a screenshot sent to the person in it are the best ones. If his involves a message about a girl, you are allowed one follow-up and no more.
What are your three most recent emojis, and what do they say about your week?
Why ask it
Recents are hard to fake, which is the point. Over text he just sends them, and in person you make him hold up the screen. The skull, the crying-laughing face and the plain thumbs up are three very different guys, so show him yours and let him judge you too.
What are you way too competitive about for no good reason?
Why ask it
Board games, parking spots, who walks faster. A guy who can admit it is easier to play against than one who says he does not care about winning. The natural next move is to challenge him at whatever he names.
If you swapped lives with one of your friends for a week, who would it be and what would go wrong first?
Why ask it
You find out who his friends are without asking for a list, and you hear how he talks about them when they are not around. Affectionate insults are a good sign.
What are you scared of that you know is ridiculous?
Why ask it
Moths, mascots, the drain at the deep end of the pool. Keep it to silly ones and leave real fears for the Deep round. Laugh with him, admit one of your own, and do not use his against him later, however tempting a moth emoji is.
What's your guilty pleasure: the song, show or snack you'd rather your friends never found out about?
Why ask it
The answer is nearly always something aimed at people half his age or twice it: a kids' movie, a baking show, his mom's playlist. Promise to keep it to yourself, and then do. Confess yours straight after, so it is a trade and he is not the only one exposed.
What nickname have you been stuck with, and who's still allowed to use it?
Why ask it
There is always a story, usually from a team or an older brother. Do not start using the name yourself straight away. Ask whether you could earn the right, which is a small flirt hidden inside a joke.
Flirty
What does your perfect first date look like, start to finish?
Why ask it
The question everyone expects in this game. Tell him which part of his answer you would enjoy and which part you would change, because 'sounds fun' ends the turn and an opinion starts a conversation.
What's the first thing you notice about a girl?
Why ask it
Most guys say eyes or a smile because it is the safe answer, so ask what the second thing is. That one is usually truer. Skip it when his friends are listening, since he will only perform for them.
Who was your first crush, and did they ever find out?
Why ask it
Far enough back to be harmless, and the story usually stars a seven-year-old with a plan that went nowhere. You hear whether he was a kid who said something or one who stared from across the room, and whether that has changed.
Love at first sight: real, or something people decide afterward?
Why ask it
Safe to ask early in a flirty game, because it is about love in general and not about the two of you. Whichever side he takes, ask whether it has happened to him. The pause before he answers is the interesting part.
What do you look for in a girl, going by the ones you've actually liked?
Why ask it
The second half is there to stop him reciting a list. He has to think of real people, and what they had in common is his type whether he would call it that or not. Check the description against yourself, but do not ask him to do it for you.
What did you think of me the very first time you saw me?
Why ask it
Only ask if you can take an honest answer. 'I thought you were stuck up' is common and nearly always followed by 'and then we talked'. Have yours about him ready, because this is one he is certain to throw back.
Which famous person did you have a crush on growing up?
Why ask it
The growing-up version is funnier than the current one and sets up no comparison with you. Expect someone from a kids' show, or now and then an animated character, which he will regret telling you.
Are you secretly a romantic, or do you leave that to the movies?
Why ask it
The usual result is a guy who says 'no' and then describes something thoughtful he once did. Ask for an example in place of a yes or no. Leave it out with a guy you met today: it asks for a soft side before he knows you.
What's a small thing a girl does that you find cute, even when she has no idea she's doing it?
Why ask it
The answers are oddly specific: tucking hair behind an ear, getting competitive over a board game, laughing before the joke is finished. If he describes something you do, he probably knows it. Let it go by without comment and enjoy it.
Would you rather be asked out or do the asking?
Why ask it
A practical question in a flirty costume. If he says he would love to be asked, he has told you what would work on him. If he insists on doing the asking, he has told you to be patient.
What do you get complimented on the most, and do you believe it?
Why ask it
He gets to repeat a compliment without sounding vain, since you asked. The second half is where it turns sweet, because plenty of guys do not believe the nice things they hear. Add one of your own that he did not mention.
How do you show someone you like them: words, time, gifts or doing things for them?
Why ask it
Then think back over the last few weeks. If he shows it by doing things, he may have been telling you for a while by fixing, carrying or saving you a seat. You also learn what to watch for in place of a text that says it outright.
What's a deal breaker for you, big or small?
Why ask it
'Big or small' lets him start with a silly one. Asked lightly, it gets you rudeness to waiters or never asking a question back. Asked heavily, it gets a long story about a past girlfriend, so keep your tone easy.
Where would you take me if you wanted to show off your favorite place?
Why ask it
It makes him picture the two of you somewhere, which is all a flirty question has to do. A specific place means the invitation is half made. 'I'd like to see that' finishes it without you having to ask him out.
What do you like most about me so far, if you had to pick one thing?
Why ask it
Needs a little history, so not for a first conversation. 'One thing' keeps it from being a request for a speech, and 'so far' leaves room for more. Thank him and take your turn: asking for a second thing spoils the first.
What's the bravest thing you've done because you liked someone?
Why ask it
Walking across a cafeteria counts. So does sending the first message. If his answer is 'nothing yet', smile, say there is still time, and take your turn before he has to respond.
Which couple from a movie or a show would you most like to be half of?
Why ask it
Expect a groan first and a name second. The pair who bicker for six seasons and the pair who were best friends first are two different wishes. Ask which half he would be, and do not volunteer to be the other one until he asks.
Dream night: dressed up and out somewhere, or sweatpants and a movie?
Why ask it
An either-or is the easiest kind of flirty question to answer by text. Most people say sweatpants, and then you get to ask which movie and who is in charge of the snacks.
Texting all day, or saving it up for when you see each other?
Why ask it
If you are playing over text, he is answering about the conversation he is in, and he knows it. 'Depends who it is' deserves the follow-up 'and for me?'. Ask it once and take whatever you get.
What could someone do on a completely normal day that would make your whole week?
Why ask it
A change of pace from teasing. The answers are small: a message before a big game, food turning up, someone remembering what he said last week. You may well find a use for what he tells you.
Do you have a crush on anyone right now, and do I know them?
Why ask it
Most people start a game of 21 with a guy in order to get to this one. Keep it until late and ask it lightly, ready for any of three answers: a name, a 'maybe', or 'do you?'. That third one is the best sign, and it means you have to answer.
Deep
What's your best memory from when you were a kid?
Why ask it
A deep question that is pleasant to answer, so a serious game can start with it. Small scenes come up more than big events: a fishing trip, a kitchen, a backseat at night. Ask what he can still hear or smell from it.
What's your proudest moment so far, and who was there to see it?
Why ask it
Who saw it changes what kind of pride it is. A moment with a parent or a coach in the stands is one kind, and one nobody clapped for, such as getting a little brother through a bad year, is another. Tell him it is impressive, plainly, once.
Who do you look up to most, and what would you copy from them?
Why ask it
A dad, a coach, a grandfather, an older cousin. Whatever he would copy is a description of who he wants to become, so remember it. If nobody comes to mind, do not push, since that can be a sore spot.
What do you hope your life looks like in five years, and which part are you least sure about?
Why ask it
The first half sounds like a job interview, and the second half is there to make it human. A guy still in school may see no further than graduation, which is a fine answer. Listen for whether the plan is his or his parents'.
What would you chase if money and other people's opinions didn't count?
Why ask it
Take away the two usual excuses and see what is left. Often it is something creative or somewhere far away. If he says he would change nothing, he is either very lucky or not ready for this one yet, so move on.
What's something almost nobody knows about you?
Why ask it
He decides how much it weighs. Some guys offer a fun fact and some offer a secret. Whichever it is, he chose to tell you, so it does not get repeated to your friends, however good it is.
What are you most afraid of, once you get past easy answers like heights?
Why ask it
With heights and spiders ruled out, you tend to get failing, being alone, or letting his family down. Do not try to talk him out of it or promise it will never happen. Say you get it, then give him yours at the same size.
What's one choice you'd make differently if you got a second try?
Why ask it
Gentler than asking for his biggest regret, because a choice can be small: a team he quit, a school he picked. If he gives you a big one, he is trusting you with it. Ask what he would do differently and leave the why alone.
If you could change one thing about yourself overnight, what would it be?
Why ask it
Listen for whether he names something about how he looks or how he acts. Resist the reflex to say 'but you're perfect', which shuts the door. 'I've never noticed that' is kinder and is usually true.
Would you rather be respected or liked, if you could only have one?
Why ask it
A big question with no personal risk in it, so it works as a breather in the middle of a serious game. Most guys answer fast and then start arguing with themselves. Ask who he learned that from.
What's the most important thing the people who raised you taught you?
Why ask it
The wording leaves room for a grandparent, a stepdad or an older sister, which matters when you do not know his family yet. Some guys answer with a lesson they kept, and some with one they are determined to do differently.
What's the one thing you can't forgive in a friend?
Why ask it
This is his line, and people tend to draw it where they have been hurt before: lying, talking behind his back, vanishing when things got hard. He is also telling you what he will expect from you, so take note of it.
Who do you go to when something is really wrong?
Why ask it
You learn who his person is: a brother, a mom, a friend since kindergarten. 'Nobody, I deal with it myself' is a common answer, and it deserves a gentle 'does that work?'. Ask that once and let it be.
What gets you choked up, even when you try to hide it?
Why ask it
Plenty of guys have been teased for this, so ask it kindly and never in front of anyone else. A movie about a dog is a full answer. Do not laugh unless he laughs first.
Have you ever been in love, or thought you were at the time?
Why ask it
'Or thought you were' lets him answer without declaring anything, and a crush at fourteen is a fair reply. You are not asking for a name or the whole story. If the answer is yes, 'how did you know?' is the one follow-up worth a turn.
What do you want from a relationship, if you want one at all?
Why ask it
What a first date is to a flirty game, this is to a serious one. Believe what he says, including 'I'm not looking for one right now'. Hearing that inside a game beats guessing at it for three months.
Can you see yourself as somebody's husband or dad one day?
Why ask it
It is about the picture in his head and not about you, which is what makes it safe to ask. A quick yes, a firm no and 'I've never thought about it' are each worth knowing. Do not ask it in the first week.
What's something hard you got through that changed you?
Why ask it
Keep this for a guy you have known a while, somewhere nobody can overhear. Let him choose how much to tell. When he stops, the best reply is your own answer at about the same length, so he is not the only one who opened up.
What do you want people to remember you for?
Why ask it
Big, so give him a moment and do not fill the silence. Whatever comes out, being funny or being someone people could count on, is what he is working at being now. Ask how he thinks he is doing.
Where are you when you feel the most like yourself?
Why ask it
On a field, in a garage, with two particular friends, alone with headphones on. A calm question that still goes somewhere. If he says 'right now, sort of', that is about the best thing a guy can say in this game.
What have you learned about me today that you didn't expect?
Why ask it
A good way to close any game of 21, because it turns the whole thing around and shows you what he was paying attention to. If he brings up a small answer you gave near the start, he was listening the entire time.
How to play 21 Questions with a guy
Practical guidance for the conversation itself
How the game works
The two-line version
Take turns asking each other one question at a time until you have each asked 21. Every question gets an honest answer or a pass, and he can throw any question straight back at you.
You answer your own questions
Before you ask anything, check that you would answer it yourself, because 'what about you?' is a legal move at any point and he will use it. Having your answer ready keeps the game even. A guy who has answered ten questions and heard nothing back starts to feel examined.
Passes cost nothing
Give each player three passes and never ask why one was used. If he passes, make your next question an easier one, not a harder version of the same thing. The passes are yours too: if he asks something you would rather not answer, pass, and if he keeps pushing after a pass, end the game there.
Four rounds of 21
This page holds four rounds of 21 questions each, 84 in all: Easy, Funny, Flirty and Deep. Each round is a complete game on its own. Play one round in a sitting and stop there, or build your own 21 from several rounds. Nobody needs all 84 in one night.
Which round to play
You have just met, or barely talked
Play Easy. Nothing in it asks him to be funny on demand or to admit anything, which is right for someone you met this week or a guy from class you have only said hi to. If his answers get longer as the round goes on, he is enjoying it, and you can borrow a few from Funny before you stop.
You already joke around
Play Funny. It suits a guy who is a friend first, a group chat, or a slow afternoon. The questions are there to be argued with, so disagree with him often. How he takes being teased is the main thing this round shows you.
You like him and think he might like you
Play Flirty, after a few Easy or Funny questions and not cold. The round stays with crushes, compliments and dates, and goes no further than that. If he answers the first two in a few words and does not send one back, switch rounds. Nothing is lost, and you have your answer for today.
You know each other well
Play Deep, with only the two of you there and nowhere to be. It is the wrong round for a first conversation and for a group, where a serious answer gets a laugh it did not ask for. Answer every question you ask in it, at the length he did.
Building a mixed game
Seven questions from each of three rounds makes 21. Easy, then Funny, then Flirty is the usual order for a guy you like, and Easy, Funny, Deep for a friend you want to know better. Move to the next round only when the last few answers came easily.
Playing over text
Start it with one line
Send 'Want to play 21 Questions? You go first.' Letting him ask first shows him the game runs in two directions, and his first question tells you which round he is in the mood for.
Send one question at a time
Send a single question, wait for the answer, say something about the answer, and only then take your next turn. Three questions in one message read like a form to fill in. A line of your own about what he said is what keeps it from feeling like a quiz.
It does not have to finish tonight
A game over text can run for days. Number the questions ('Q7') so you both know where you are, and pick it up after school or work at the next number. An unfinished game is a ready reason to message him tomorrow.
What to keep off the screen
Messages can be screenshotted and passed around, so do not ask or answer anything by text that you would mind his friends reading. Hold the heavier Deep questions for a call or for sitting next to each other, where you can hear how he means it.
Reading his answers and keeping it kind
Short answers
One-word replies usually mean the question was too big for where the two of you are, not that he is bored. Go back to Easy, give one long answer of your own, and watch whether his answers grow.
When he throws one back
'What about you?' is the best thing he can say. It means he is curious about you, which is what the game is for. Answer at the length and honesty you were hoping to get from him.
What stays in the game
Whatever he tells you in a Flirty or Deep round stays between the two of you. Do not repeat it to friends, and do not bring it up later as a joke. If a question lands badly, say 'skip that one' and take an easy turn yourself.
Knowing when to stop
Twenty-one each is the limit, not the goal. If you reach question nine and realize you have been talking about one answer for half an hour, the game has done its job, and you can stop counting.