21 Questions to Ask a Girl
For playing 21 Questions with a girl you like, in person or over text: you take turns asking, she can throw any question back at you, and you answer your own too. This page holds four full rounds of 21, 84 questions in all: an easy round for someone you've just met, a funny round, a flirty round and a deep round for when you know each other. Every question has a note on how to follow it up, how to answer when it comes back to you and which ones to save for later.
One at a time · 01 of 84
Easy round
“What does a Saturday with nothing planned look like for you?”
Why ask it
An easy opener, since nobody has a wrong Saturday. Notice whether her free day is full of people or happily empty, and know what yours looks like, because she will probably ask.
Want questions from the whole vault instead? Try the random question generator.
The questions
Each question, and why to ask it
Easy round
What does a Saturday with nothing planned look like for you?
Why ask it
An easy opener, since nobody has a wrong Saturday. Notice whether her free day is full of people or happily empty, and know what yours looks like, because she will probably ask.
Where did you grow up, and what's the one thing I'd have to see or eat there?
Why ask it
Fine to ask even if you're from the same town, because then you can argue over the one spot a visitor shouldn't miss. Notice whether she describes the place fondly or as somewhere she left. Have your own hometown pick ready, since she'll want to hear it.
What's the last show you finished, and should I watch it?
Why ask it
The second half makes her the expert and gives you homework you can report back on. When it's your turn, name one show and say why in a sentence. A list of six ends the conversation.
Which three songs have you played most this month?
Why ask it
Asking about this month gets what she really listens to, not the favorite band she has named since ninth grade. Over text, ask her to send one, and listen to it before you reply.
Morning person or night owl, and what happens if someone talks to you at the wrong hour?
Why ask it
She knows which one she is without thinking, so the story is in the second part: the night owl facing a 7 a.m. alarm, the early riser at a party past eleven. If you turn out to be opposites, tease her about it now and plan around it later.
Do you have a pet, or which animal would you bring home tomorrow if you could?
Why ask it
Works either way: she has one and shows you forty photos, or she doesn't and describes the dog she has already named. Ask the pet's name, real or imagined, and the next ten minutes take care of themselves.
Someone hands you a boarding pass for a flight that leaves tonight: where do you hope it's going?
Why ask it
'Tonight' rules out the carefully planned dream trip and gets the place she'd go on impulse. Ask who she'd bring and what she'd eat first. When it's your turn, pick somewhere you'd really go, not somewhere impressive.
If you had to eat the same dinner every night for a month, what would you choose?
Why ask it
A month is long enough that she has to think and short enough to stay funny. Remember the answer for the next time you're choosing where to eat. If hers is something you can't stand, say so and let her argue for it.
Do you have brothers or sisters, and what did you fight about most as kids?
Why ask it
The front seat, the remote, borrowed clothes that came back stained. Old fights are told fondly now, which keeps this on the funny side of family. An only child can tell you what she got all to herself and whether it was worth it.
Which day of the year do you look forward to most: a holiday, your birthday or something only your family does?
Why ask it
The third option is where the good answers are: a yearly lake trip, a cousin sleepover, pancakes on the first day of snow. Ask what would ruin the day if it went missing.
What's your star sign, and does it sound anything like you?
Why ask it
She gets to describe herself by agreeing or arguing with the chart, which is easier than being asked to describe herself outright. Know your own sign before you ask, and be prepared to hear what it says about you.
What movie can you quote from start to finish, and who made you watch it the first time?
Why ask it
Ask for a line and she'll usually do the voice, which is a good sign the game is going well. The 'who made you watch it' part introduces a sister, a dad or a best friend without you asking about them directly.
Do you have a hidden talent, and can you show me right now?
Why ask it
The demonstration is the fun of it: a cartwheel, an accent, writing backward. In a text game, ask for a video or a voice note and offer to send yours in return.
Who's your closest friend, and how did the two of you meet?
Why ask it
People light up describing a best friend, and the how-we-met story is usually a good one. Remember the friend's name. You will hear it again, and it's good to already know who she is.
What's your biggest pet peeve, the small thing that gets to you every time?
Why ask it
Complaining about something tiny is oddly bonding, so once she has named hers, add yours to the pile, whether it's wet sleeves or a phone on speaker in public. If you do the thing she names, admit it before she notices.
What did you want to be when you were seven, and does any of it still show?
Why ask it
Traces tend to survive: the kid who wanted to be a teacher is often the friend who explains things, and the would-be vet still stops for every dog. Ask which part of the job she'd still take. Give your real answer too, even if it was garbage truck driver.
What subject could you give a full hour's talk on with zero preparation?
Why ask it
Then let her, at least for a few minutes. Someone talking about the thing she loves is at her most relaxed, and you find out what to ask about next time.
What's one good thing that happened to you today?
Why ask it
Good as a first message because it asks for news, not a biography. If her day has been rough she'll say so, and you can either ask about that or send a sillier question to cheer it up.
You get one superpower, but only for a day: which one, and what's the first thing you do with it?
Why ask it
The power matters less than the first use. Flying to the beach, reading one particular person's mind, pausing time for a nap: each says something different. Have a silly answer and a real one for when she throws it back.
What's on your bucket list that you could actually do this year?
Why ask it
'This year' turns a someday list into something close to a plan. If one of hers sounds like something you'd enjoy too, say so and leave it there for now.
What's something about you that surprises people when they find out?
Why ask it
How surprising to be is up to her: a black belt, a twin, a year lived abroad. Whatever she picks is the thing she'd like you to know next, so ask about it before you move on.
Funny round
What's a story about you that was mortifying at the time and is funny now?
Why ask it
Asking for one that has turned funny keeps out anything that still hurts. Tell yours in full when she asks, tripping included. This round only works if both of you look a bit silly.
Pineapple on pizza: yes, no, or should we not have this conversation yet?
Why ask it
There is no winning this argument, which is the appeal. Take the opposite side for a minute even if you agree with her. A pretend fight this early shows you can disagree and both still be laughing.
Which animal do you think is quietly judging people the hardest?
Why ask it
Cats get blamed a lot, and so does any goose near a pond. Ask what the animal is thinking, because the impression is where the laugh is. Nobody has a prepared answer to this, so it works even on someone tired of the standard questions.
What are you scared of that makes no sense at all?
Why ask it
Laugh with her, never at her, and offer one of yours in the same breath, even if it's only moths or the automatic flush. Don't test the fear later as a joke.
If you came with a warning label, what would the small print say?
Why ask it
'Do not approach before coffee' or 'will cry at dog commercials'. She gets to tease herself, and under the joke there's usually a true instruction. Write yours in advance, since it's harder than it sounds.
What's the worst pickup line anyone has ever tried on you?
Why ask it
An easy story to tell, because she comes off well in it and someone else looks ridiculous. It's also a quiet guide to what not to do. If she asks for the worst one you know, deliver it with total commitment.
Which chore would you pay real money never to do again?
Why ask it
Her hatred will be specific and heartfelt, and it's usually fitted sheets or anything involving a drain. Offer to trade it for the chore you can't stand, then argue about who got the better deal.
What's the most effort you've ever put into not getting off the couch?
Why ask it
Dragging the remote closer with a foot, eating cereal with a fork because the spoons were dirty, turning off a light with a thrown sock. There's no shame in any of it, so it's easy to answer honestly. Yours should be worse than hers.
In a zombie movie, what's your job on the team, and how long do you last?
Why ask it
The comedy is in how she ranks herself, anywhere from leader to the one who trips in the first ten minutes, and you're allowed to argue with her verdict. Then ask where she'd put you on the team.
What excuse do you use most to get out of plans?
Why ask it
She knows hers instantly, whether it's a headache or an early start. Then ask, grinning, whether she has ever used it on you, and take whatever she says well.
What's the strangest photo on your phone right now?
Why ask it
Made for a text game, since she can send the evidence. Don't press if she'd rather describe it than show it. A blurry picture of a pigeon with a long explanation is the ideal result.
If you won the lottery tomorrow, what's the first completely unnecessary thing you'd buy?
Why ask it
Everyone says they'd pay off the house, so 'unnecessary' is there to get the real wish: an indoor slide, a personal smoothie chef, one sneaker in every color. Then ask what she'd buy once the novelty wore off.
What did you believe as a kid for way longer than you should have?
Why ask it
That swallowed gum stays for seven years, or that teachers lived at school. These beliefs are usually someone's fault, so ask who told her. It's embarrassing in a harmless way, and safe with someone you barely know.
If you were a villain, what would your very minor crimes be?
Why ask it
It shows her sense of humor more than her morals, so expect crimes on the scale of taking the last slice or hiding one sock from every pair. Volunteer as her accomplice and confess a crime of your own.
You're stuck on a desert island and can bring three things, none of them useful. What do you pack?
Why ask it
Banning useful things kills the dull answers about knives and matches. What's left is comfort: a blanket, a playlist, a particular snack. You learn what she reaches for when things go wrong.
What's your karaoke song, and is it a good choice or just a confident one?
Why ask it
If she says she would never do karaoke, ask what she performs alone in the car. Either way you have learned a song you can put on at the right moment later.
What's the most ridiculous argument you've ever won, or refused to lose?
Why ask it
Whether a tomato is a fruit, how to say 'gif', which way the toilet paper hangs. She will get heated all over again while telling it, which is the fun. Don't reopen the argument unless you're prepared to lose it too.
What's your guilty pleasure, the show or song you'd never put on with other people in the room?
Why ask it
Name yours first if she hesitates, and make it properly embarrassing, because a guilty pleasure tends to come out only after someone else has gone first. If you know the show or song she names, quote a line of it. Don't call it bad, even as a joke.
What's the least cool way you've ever hurt yourself?
Why ask it
Keep this to bumps and bruises: walking into a glass door, a stapler incident, falling up the stairs. If the story starts to sound serious, drop the jokes and just listen.
One horse-sized duck or a hundred duck-sized horses: which fight do you take?
Why ask it
An old internet question that still starts a real debate. Make her explain her strategy, then pick the other side and defend it. How seriously she plans the fight is the entertaining part.
What would the movie of your life so far be called, and who plays you?
Why ask it
The title is a one-line summary of how she sees her own story, and the casting is pure vanity. When it comes back to you, cast someone far too good-looking with a straight face. She will enjoy correcting you.
Flirty round
When you meet someone new, what do you notice before anything else?
Why ask it
A gentle way to start flirting, because she can answer about people in general: hands, voice, whether they thank the waiter. Expect her to ask what you noticed about her, and make your answer specific and kind.
Who's your celebrity crush, and how long has it been going on?
Why ask it
Safe flirting, since the person is nowhere near the room. Don't compare yourself to them out loud. Ask what the appeal is, and if she says funny or kind, that tells you more than the name did.
Do you have a type, or do you only find out when it's standing in front of you?
Why ask it
Plenty of people say they have no type and then describe one in detail. Listen without auditioning for the part. When she asks you back, describe qualities, not a checklist of looks.
What's more attractive: a great smile, a good voice, or someone who makes you laugh?
Why ask it
A pick-one question gets a quick answer, and she will probably add a fourth option of her own. Her pick tells you what you can stop worrying about. If she turns it around, answer with something true about her and not a line.
What's your biggest ick, the small thing you can't unsee once a guy does it?
Why ask it
Expect something oddly specific, like running for a bus with a backpack on. Laugh, and don't promise never to do it. Skip this one if you're easily rattled, because you will spend the rest of the day checking yourself.
Who was your very first crush, and what did you do about it?
Why ask it
Usually the answer is 'nothing at all' or 'gave him half my sandwich', and both are charming. Old crushes are safe ground because nobody has anything at stake anymore. Trade yours, name included.
When you like someone, do you get louder or quieter around them?
Why ask it
Of all the flirty questions, this one is the most useful to you. If she says quieter, a short reply may not mean what you feared. Tell her which one you are and she can do her own math.
Do you believe in love at first sight, or is that just a very good first impression?
Why ask it
A light debate with a real opinion under it, and romantics and skeptics both enjoy defending their side. Don't steer it toward the two of you yet. It works best as a general question.
What's your favorite love story from a movie, a show or a book?
Why ask it
Her pick shows what romance looks like to her: slow and friendly, dramatic, or two people bickering for six seasons. Ask which scene she'd rewatch. If you don't know the story, ask her to pitch it in three sentences.
What do your friends say about your taste in guys?
Why ask it
Putting it through her friends lets her be honest and funny at once, and 'they've given up' is a perfectly good answer. Leave past boyfriends alone unless she brings them up herself.
Flowers, a handwritten note or your favorite snack turning up unannounced: which one wins?
Why ask it
All three are small and none costs much, which is why her choice is worth remembering. If she picks the snack, it's because it proves someone paid attention. Don't deliver it the next day. Wait for a day that needs it.
What's the nicest surprise anyone has ever pulled off for you?
Why ask it
It doesn't have to be romantic, and one from a friend or a grandparent is just as good. Listen for the size of it. For some people it's a party in a decorated garage, and for others it's a saved seat.
Do you like it when a guy makes the first move, or would you rather make it yourself?
Why ask it
Ask this before you make one. Her answer saves a lot of guessing, and if she says she prefers to go first, the kind thing is to make that easy and not to rush her.
Being asked out: better in person, or in a text you can read twice?
Why ask it
Some people find being asked in person brave, and some find it a lot of pressure with nowhere to look. Once she has told you which she is, you have no excuse for doing it the other way.
What would a date need to have for you to tell your friends about it afterward?
Why ask it
Less about a perfect date and more about what she'd count as memorable: good food, a surprise, someone who made her laugh until she had to sit down. Take notes in your head, not on your phone.
What's the boldest thing you've ever done to get someone's attention?
Why ask it
You get a story and a measure of how brave she is when she likes someone. If she says she has never done anything bold, that's worth knowing too. Your own answer should be true, even if it's small.
Did you look me up online before we started talking, and what did you find?
Why ask it
Plenty of people do, and admitting it is funny. Confess your own search first if she stalls. Keep it light, and don't quiz her about an old photo she'd rather you forgot.
What did you assume about me before we had ever talked?
Why ask it
Only for someone you've talked to more than once. Brace for 'quiet' or 'full of yourself', and laugh at either. When she asks for yours, lead with the guess that turned out to be right and good.
Are you talking to anyone right now, or am I allowed to keep flirting?
Why ask it
Direct, so keep your tone light, and hold it until she has flirted back at least once. A yes is useful to hear and should be taken graciously. A no, said with a laugh, is your sign to carry on.
What do you think I'm like on a date: smooth, nervous or trying too hard?
Why ask it
She has to picture a date with you to answer, which is the whole idea. Whatever she guesses, admit that the truth is probably nervous. A little honesty there lands better than pretending to be smooth.
This is my last question of the round: can I take you out sometime?
Why ask it
Ask it only if her answers have been warm and she has been sending questions back all along. Have an actual plan ready, with a day and a place. If she says no or not yet, thank her for the game and mean it.
Deep round
Which version of you do your closest friends get that nobody else sees?
Why ask it
A soft way into the serious questions, because that version is usually louder, sillier or more opinionated, and she will enjoy describing her. Ask how long it takes someone to meet that side. Then describe yours.
Who do you look up to most, and what do they do that you'd like to copy?
Why ask it
The second half moves it from naming a hero to describing a way of living. It's often a grandmother, an older sister or a coach. When she asks you, pick someone you know in person over someone famous.
Who in your family are you most like, and how do you feel about that?
Why ask it
She will usually name the person fast and then take a while over the second half. A shared temper and a shared laugh both come up, so don't assume it's a compliment or a complaint until she says. If family is a sore subject she can keep it to one line, and you should let her.
What moment in your life so far are you proudest of?
Why ask it
Let her brag, and don't follow it with a bigger one of yours. Ask what it took. The work behind the moment usually says more about her than the moment does.
What's your happiest memory, the one you'd replay first?
Why ask it
Give her time, because people tend to scroll through a few before choosing. The details she includes, like who was there and what the weather was doing, are worth asking about. Answer it yourself right after, so it feels like a trade.
What's your best quality, and which one gets you into trouble?
Why ask it
Often it's the same trait with the volume turned up: loyal and stubborn, honest and blunt. When it comes back to you, name a real flaw. 'I care too much' doesn't count, and she will know it.
What did you used to be insecure about that doesn't bother you now?
Why ask it
Asking about one she is past keeps it safe, and the story ends on a win. Don't tell her the insecurity was silly, even kindly. Ask what changed, and share one of your own that you have also outgrown.
What's your biggest fear that has nothing to do with bugs, heights or the dark?
Why ask it
Not for the first week of knowing someone. What comes up is often about people: being left out, letting someone down, losing someone. Don't try to solve it. Thank her, then answer at the same depth.
On a bad day, what helps most: advice, a distraction or someone sitting with you?
Why ask it
Worth asking even if you skip everything else in this round. It's easy to assume everyone wants what you would want, and this saves you from guessing wrong. Tell her yours too, then remember hers when the bad day comes.
If money didn't matter, what would you do with your days?
Why ask it
The classic daydream, and still a good one. Notice how close the answer is to what she's doing now. If it's far off, ask what a small step toward it would look like, and resist turning it into a pep talk.
Where do you want to be five years from now: which city, what work, who's around?
Why ask it
The three parts stop it from sounding like a job interview. She doesn't need a plan, and a shrug is a fair reply. Notice which of the three she is surest about, and ask about that one.
What dream are you a little embarrassed to say out loud?
Why ask it
She is taking a risk by telling you, so keep a straight face even if it's becoming a famous singer. Ask how long she has had it. Skip this one unless you'd answer it honestly yourself.
If you got one do-over, big or small, what would you spend it on?
Why ask it
Softer than asking for her biggest regret, though it leads to the same place. 'Big or small' lets her pick a haircut over a heartbreak if she wants. Ask what she'd do the second time, not why she got it wrong the first.
What's been the hardest year of your life so far, and what changed after it?
Why ask it
Keep this for someone you've known a good while, on a day with time to listen. She can name the year without explaining it, and that's enough. The 'what changed' half lets her finish on what she took from it.
What would someone have to do to lose your trust, and could they get it back?
Why ask it
You're hearing her rules, and rules like these tend to come from experience. Don't ask who did it. If she says trust doesn't come back, take that seriously and don't debate it.
Do you believe in fate, or do you think we're mostly making it up as we go?
Why ask it
A bigger-picture question that gives you both a breather from personal history. You don't have to agree. Ask what in her own life made her think so, and tell her which way yours points.
Have you ever been in love, and how did you know?
Why ask it
A no is as complete an answer as a yes, and 'I thought so at the time' is fair too. Ask about the knowing, not about the person, so it doesn't turn into a conversation about an ex. When she sends it back, don't claim more or less than is true just to match her.
What are you actually looking for in a relationship right now?
Why ask it
Only ask if you're ready for any of the usual answers. 'Nothing serious', 'something real' and 'I don't know yet' are all fair, and each tells you where you stand. Be just as plain when she asks you.
Do you see marriage or kids in your future, or is it too early to say?
Why ask it
Far too much for someone you've just met, and fine between two people who have been talking for months. Treat it as curiosity, not a negotiation. If your answers differ, nobody needs to settle it during a game.
If you had five minutes with yourself at thirteen, what would you tell her?
Why ask it
The answer is usually reassurance: it gets better, stop worrying about that group, keep drawing. It shows what was hard at that age without asking her to relive it. Yours will probably be embarrassing, which helps.
Of everything we've asked each other, which of my answers surprised you most?
Why ask it
Save it for the very end of the game. It tells you what she heard and what stuck, and it hands the last word to her. It only works if you've been answering your own questions all along, or she will have nothing to choose from.
How to play 21 Questions with a girl you like
Practical guidance for the conversation itself
The rules in two lines
The whole game
You ask one, she asks one, and you keep going until you have each asked 21. Whoever is answering can throw the question straight back, and then the asker has to answer it too. Those are all the rules. Everything else here is about playing it well.
Answer your own questions
Before you ask anything on this page, know what you would say to it. She is likely to send it back, and 'I don't know, I only wanted to hear yours' takes the air out of the game. A fair rule for both players: never ask what you wouldn't answer.
Agree on skips before you start
Give each player three skips with no explanation owed, and say so at the start, so that using one feels like part of the game and not a refusal. When she skips a question, let it go. Asking it again later in different words is the quickest way to end the game.
Follow-ups don't count
A 'why?' or a 'then what happened?' is free and doesn't come off anyone's 21. If one answer turns into ten minutes of talking, stay there. Nobody is keeping score, and the questions are only a way to get the two of you talking.
Four rounds, and which one to play
Each round is a full game
The list is four rounds of exactly 21, so one round is one complete game for the person asking. You don't have to play all four, and you can ask a round in any order you like. Pick the one that fits how well you know her and keep the others for another day.
Just met: the easy round
With someone you met this week, stay in the easy round. Every question in it can be answered in a sentence by a person who doesn't know you yet, and none asks about family trouble, exes or feelings. If she starts giving long answers and asking you things back, borrow a few from the funny round.
Funny comes before flirty
The flirty round reads very differently after twenty minutes of laughing than it does cold. Play the funny round first, or at least a handful from it. It also shows you what kind of teasing she enjoys, so you aren't guessing when you try it.
Flirty only when it goes both ways
The flirty round starts general and ends on the two of you, with a real invitation as question 21. Ask the last five only if she has been flirting back. If her answers get shorter, drop to the funny round without comment. If she says she isn't interested, believe her the first time and either carry on as friends or call it a good game.
Deep is for later
The deep round is for someone you already know, and it rarely belongs in the same sitting as a first conversation. It doesn't have to be played all at once. Three of these questions on a long walk can be a whole evening, and the notes flag the ones that need the most trust.
Playing over text
One question per message
Send a single question and wait for the answer. Three at once looks like homework, and only the easiest one will get a reply. Tell her up front that it's a game of 21 Questions, so a run of questions makes sense and she knows she gets to ask too.
Reply to the answer before you ask again
The common mistake by text is firing the next question the second her answer lands. Say something about what she wrote first, even one line, and answer the question yourself if she sent it back. Then ask the next one.
Let it run for days
A text game doesn't need to finish in one night. Three or four questions an evening can carry a round through a week, and the evening message becomes something she expects. Don't time her replies, and don't send a second question because the first has gone unanswered for an hour.
Use what a phone is good for
Some questions are better by message than in person: the three songs she has played most, the strangest photo on her phone, the hidden talent sent as a video. Ask for the evidence and send your own. Save the end of the flirty round and most of the deep round for a phone call or the next time you see her, when she can hear how you mean it.
When the game stalls
She answers in one word
Go back to the easy or funny round and answer the next question yourself, at length, before she does. Often a short answer means she isn't sure how much you want to hear. If the answers stay short after that, wrap up warmly and try another day.
She never asks anything back
Remind her once that it's her turn, and offer her the page so she can pick. Some people need permission to ask. If she still doesn't, you are running an interview, so stop at a natural point well short of 21.
A question lands badly
Say 'forget that one, it wasn't a good question' and move on with something light. Don't ask why it bothered her and don't apologize three times. Then let her ask the next one, so the turn is hers again.