Cute Questions to Ask a Guy
Cute questions to ask a guy you like, or one you have just started seeing, for when you want to make him smile and not put him on the spot. The 79 questions come in the order you would use them: Easy and sweet, When he was little, His soft side, About you two, Daydreams and Goodnight texts. The first two groups never mention the two of you, so they are safe with a crush you have barely spoken to, and the notes say which of the later ones to save until he has shown he likes you.
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The questions
Each question, and why to ask it
Easy and sweet
What always makes you smile, even on a bad day?
Why ask it
A warm first question that nearly everyone can answer, and the answer tends to be a dog, a little cousin or one particular song. Ask to see it or hear it right then, because watching him light up over a photo of his dog is the reason to ask. Have your own answer ready, since he will want to know.
Are you a hugger, or do you need a warning first?
Why ask it
Either answer is endearing: the guy who hugs everyone and the one who goes stiff as a board. A hugger may offer proof on the spot, so ask only if a hug from him would be welcome. If he needs a warning, give him one the next time you say goodbye and watch him grin.
What's the cutest thing you've ever seen an animal do?
Why ask it
He will probably reach for his phone to show you the video, which puts the two of you shoulder to shoulder over one screen. Guys who would never call anything cute will say it about a dog without blinking. Have one of your own to trade.
What's your comfort movie, the one you've seen a dozen times?
Why ask it
A comfort movie tells you more than a favorite one, because nobody picks it to sound impressive. If it is animated or made for ten-year-olds, that is the answer you were hoping for, so do not tease. 'I've never seen it' is an easy way to be invited to watch.
What's the nicest thing anyone has said to you lately?
Why ask it
Expect a pause, because plenty of guys have to dig for this, and some will come up with a compliment from years ago. Let the pause sit. Once he has answered, add a true one of your own so his list is one longer than when you asked.
What song do you put on when you're in a really good mood?
Why ask it
Good-mood songs are rarely cool ones, which is the charm. Ask him to play ten seconds of it, or if you are texting, listen before you reply so you can say something about the actual song. Hum it near him a week later and see how long he takes to notice.
Do you have a nickname that only your family uses?
Why ask it
Family nicknames are usually left over from when he was three, and he will act embarrassed while giving you the full history. Enjoy it, and do not start using it in front of his friends. Being trusted with the name is the cute part.
What's your favorite thing to do on a rainy day?
Why ask it
More cozy than revealing: you get blankets, video games, soup or a very long nap. Listen for whether his rainy day has room for a second person in it. Asked on an actual gray afternoon, it also finds out whether he is free.
What's the one treat you'd pick after a rough day?
Why ask it
File the answer away. It will be oddly specific, a certain flavor from a certain shop, and turning up with it some week when he is stressed will mean more to him than anything you could say. No need to tell him why you are asking.
Do you sing in the car, and how bad is it?
Why ask it
Most guys will own up to it and insist they are terrible, and the confession is what makes it sweet. Ask which song gets the full performance. If you ever end up in his passenger seat, you know what to put on.
What would you name a puppy if you got one tomorrow?
Why ask it
Puppy names are hard to say without smiling. A guy with a name ready has wanted that dog for years, so ask what kind it is and where it would sleep. When he asks what you would call yours, pick something that goes with his.
What's your favorite smell in the whole world?
Why ask it
Smells are tied to people and places, so 'cut grass' or 'my grandmother's kitchen' comes with a story if you ask where it takes him. It suits an early conversation because it asks for nothing personal and usually gets something personal anyway.
What's the best gift you ever got, and who gave it to you?
Why ask it
The second half matters more than the first, since it tells you who knows him well. Notice whether the gift was expensive or just exactly right, like a mixtape or a drawing from a little sister. Useful to know before his birthday comes around.
Are you ticklish, or are you going to pretend you're not?
Why ask it
A staple of the cute list, and best with a guy you already joke around with. He will deny it, and the denial is the fun. Leave it as a question unless he is plainly inviting you to test it, because tickling someone who has not asked for it is annoying, not cute.
When he was little
What were you like as a little kid?
Why ask it
Open enough that he picks the story: the shy one, the loud one, the kid who took the remote apart to see inside. Ask whether his mom would describe him the same way, since her version is usually funnier. Then say what you were like, so it is a swap and not an interview.
What's your favorite childhood memory?
Why ask it
The classic, and it earns its place. His first answer is often a general one, like summers at his grandpa's, and the good part comes when you ask what one day there looked like. Watch his face while he tells it.
Did you have a stuffed animal or a blanket you couldn't sleep without?
Why ask it
Ask for the name. There is always a name, and a grown guy saying 'Mr. Bear' out loud is the reason to ask. If the thing still lives in a closet at his parents' house, that is his secret to share and not yours to pass around.
What did you tell everyone you were going to be when you grew up?
Why ask it
Dinosaur expert, garbage truck driver and astronaut come up a lot. The sweet follow-up is whether any piece of that plan survived: the boy who wanted to dig up bones is often still the one reading every sign in the museum.
What cartoon did you never miss?
Why ask it
If you watched it too, you have an instant bond. If you did not, he gets to explain the plot in far more detail than it needs, which is just as good. His favorite character says a little about who he wanted to be at eight.
Who was your hero when you were about seven?
Why ask it
Seven is the age of wearing one costume for a month straight, so ask what he did to be like them and whether photos exist. The hero may be somebody in a cape or an older cousin with a bike. Now and then it is a grandparent he misses, so keep it for after the easier kid questions.
What were you scared of as a kid that seems funny now?
Why ask it
'That seems funny now' steers him toward the vacuum cleaner or the basement stairs and away from anything that was truly frightening. Admit yours straight after. A guy laughing at his six-year-old self is about as relaxed as he gets.
What's the most trouble you ever got into as a little kid?
Why ask it
Kid crimes are tiny, so this stays cute and never becomes a confession: a haircut he gave his sister, a crayon mural on the hallway wall. Ask what the punishment was and whether it was fair. He will still have an opinion.
Is there a baby photo of you that your family brings out every time?
Why ask it
You are really asking to see it, and he knows. A guy who shows you without much of a fight is comfortable around you. If he refuses, 'one day' and a smile is enough, and it leaves you both something to look forward to.
What did you collect when you were little?
Why ask it
Where the collection is now is the better half of the answer. Rocks and trading cards have a way of surviving in a box under a bed, and if his did, he may offer to show you the best one. Say what you hoarded at eight so he is not the only one confessing.
What game did you make up as a kid that only made sense to you?
Why ask it
Invented games come with rules he can still recite, and the sillier they were, the more animated he gets. Ask who else was allowed to play. If you are feeling brave, ask him to teach you: learning the laws of a lava-floor game from a grown man is a very good ten minutes.
Did you have an imaginary friend when you were little?
Why ask it
If he did, the details are the treat: what it looked like, where it sat at dinner, the day it quietly stopped coming around. If he did not, ask who got the full report instead, because there was usually a dog, a toy truck or a tree in the yard that heard everything.
Who was your very first crush, back in elementary school?
Why ask it
Kept to the playground years, a classmate in second grade or a cartoon character, it stays sweet. You also hear how he acts when he likes someone, which at seven was usually hiding or chasing her around at recess. Do not slide from here into questions about exes; that is a different conversation for a much later day.
His soft side
What's something you're secretly a softie about?
Why ask it
The word 'secretly' is a promise that you will not make a big deal of it, so keep it. He might say old couples holding hands, or his little sister's school plays. 'I like that about you' is the right size of reply.
What movie made you tear up, even if you'd never tell your friends?
Why ask it
Much lighter than asking when he last cried, because a movie gives him cover. Films about dogs, dads or toys come up again and again. Tell him which one gets you, so the two of you are even.
Who in your family are you softest with?
Why ask it
A grandmother, a little brother, a niece: his voice tends to change when he gets to them. Ask what the two of them do together. Wait until you have talked a few times, since family is tender ground for some people, and move on easily if he keeps it short.
What's the kindest thing a stranger has ever done for you?
Why ask it
The stories are small ones. Someone covered him when he was short at a register, or a driver stopped to let him cross in the rain. Ask whether he has ever done the same for somebody else, and do not be surprised if he goes quiet and then says yes.
What's the cutest habit you've ever noticed in someone?
Why ask it
He has to name a real habit, like humming while concentrating or thanking the bus driver, and he will usually be picturing a specific person. Do not ask who. If the habit is one of yours he will get around to saying so, and if it is not, you have learned what catches his eye.
What's a sound you love that most people wouldn't think twice about?
Why ask it
A quick answer means he is someone who pays attention: rain on a car roof, a ball dropping through a net, his dog's nails on the kitchen floor. Offer yours too. When his sound happens while you are together, point it out before he does.
What do you do to cheer up a friend who's having a bad day?
Why ask it
Some guys bring food, some make jokes until one works, and some just sit there, which may be the best answer of the three. You are hearing how he looks after people. On a bad day of your own, you will recognize the move when he tries it.
Have you ever written someone a note or a letter by hand, and did you give it to them?
Why ask it
Birthday cards for his grandmother count, and so does the note he wrote in fifth grade and never delivered, which is the story you are hoping for. Leave it at the telling. Asking to read one, or who it was for, turns a sweet answer into an inspection.
Do you ever get butterflies, and what sets them off?
Why ask it
It asks about nerves in general, so he can say 'before a game' and stay safe or say something braver. Do not push for the braver version. Should he turn it around, 'sometimes, lately' is plenty.
What makes you blush?
Why ask it
Short enough that he may go red just from being asked. Compliments in front of other people and being sung to on his birthday are common answers. Whatever he names, do not do it to him in public for sport: a blush is only cute when the person is enjoying it a little.
What's something you've kept for years just because of who gave it to you?
Why ask it
Not the same as the best-gift question, because this thing is usually worth nothing: a ticket stub, a bracelet made by a small cousin. The follow-up is where he keeps it. A wallet or a desk drawer means he looks at it more than he lets on.
What's something sweet you've done for someone and never told them about?
Why ask it
Some guys have one and will be shy about it: the anonymous note, the chore done before anyone else woke up. Others have nothing, and that is no mark against him, since kindness done out loud counts too. From someone he has just met it can feel like a test, so give it a few weeks.
What makes you feel most at home?
Why ask it
The answers are rarely about a building. He will say a certain couch, someone's voice in the next room, a game on in the background. 'Tell me about it' is all the follow-up it needs, and it suits a guy who has moved away for school or work, when home is on his mind anyway.
About you two
What should our handshake be?
Why ask it
Less a question than a project. Build it there and then, three moves at most, and the two of you have something nobody else does. It works with a guy who is still only a friend, because a handshake promises nothing and feels like a secret anyway.
Can I give you a nickname, or do you already have one you like?
Why ask it
Asking permission is the cute part, and it keeps you from landing on a name he was teased with in sixth grade. Try two or three out loud and let him veto. The keeper is the one that makes him roll his eyes and smile at once.
What emoji is the most me?
Why ask it
Made for a text thread, and he can answer in one tap, which a shy guy appreciates. The sunflower and the little gremlin mean very different things, and both are affection. Send back the one that is most him, then use the pair as shorthand.
What do I say all the time without noticing?
Why ask it
Knowing your catchphrases means he listens closely, and he will probably do an impression. Let him. Then do your impression of him, kindly, so you have each shown the other you have been paying attention.
What's the funniest thing I've done without meaning to?
Why ask it
He gets to tease you, and you find out what he remembers, which will be something you had forgotten: a word you mispronounced, a door marked pull that you pushed. Laugh at it. Being easy to tease kindly is a large part of being easy to be around.
What's something you love that you think I'd love too?
Why ask it
He is choosing one piece of his world to hand you, whether it is a show, a taco place or a trail, so take him up on it for real. Watch the episode or try the place. Reporting back afterward is a whole second conversation.
What did you notice about me first?
Why ask it
Everyone expects this one on a cute list, and it works because it sends him back to a specific moment: your laugh, your jacket, the way you argued with a teacher. Say what you noticed about him in return. Hold it until he has given you some sign he likes you, or it lands as fishing.
What's your favorite thing about hanging out with me?
Why ask it
Easier than 'what do you like about me', since he can talk about what the two of you do. 'I don't have to try' and 'you laugh at my jokes' are bigger compliments than they sound. Tell him yours while he is still a bit pink.
Were you nervous the first time we hung out?
Why ask it
The past tense makes it safe to admit. 'A bit' is the usual answer, often with a story about changing his shirt twice or arriving early and walking around the block. If you were nervous too, say so, because finding that out is one of the nicer early discoveries.
What have you found out about me that you'd never have guessed when we met?
Why ask it
You hear how his picture of you has changed, nearly always in your favor: funnier than he thought, more competitive, worse with directions. Ask what he assumed at first. It needs a month or so of knowing each other, or he has nothing to compare.
What's one small moment with me that you keep thinking about?
Why ask it
'Small' stops it from being a declaration, so a guy you have been seeing for three weeks can still answer: the walk to the bus, the time you both got the giggles in the library. If he names one you never thought twice about, ask what made it stick.
Which of us do you think is the bigger softie?
Why ask it
A gentle argument that both of you win. He says you, you say him, and each of you has to produce evidence, which means trading the sweet things you have caught the other doing. Concede gracefully when he brings up the commercial that made you cry.
What's one thing you want us to do that we haven't done yet?
Why ask it
It only makes sense once you have done a few things together, so it suits the first weeks of seeing each other and not a crush you have barely spoken to. Keep the scale small. He says bowling, you say Saturday, and a trip can wait for a later year.
If you had to describe me to your mom in one sentence, what would you say?
Why ask it
'To your mom' is what makes him squirm, since the sentence has to be both clean and true. With a guy you are only starting to see, say out loud that it is hypothetical. If he tells you he already has, take a second to enjoy that before you ask what she said.
Daydreams
If you could wake up anywhere tomorrow morning, where would it be?
Why ask it
He can answer in one word or five minutes: a beach, a cabin, his grandmother's porch. Ask what the first hour looks like and notice the pace of it. Some guys are up a mountain by seven and some have not left the blanket.
What does your perfect date look like, down to the snacks?
Why ask it
'Down to the snacks' keeps him off the candlelit speech and onto details: mini golf, one specific pizza, who drives. A crush will hear it as a hint, so ask only if 'why, are you offering?' is a reply you would enjoy. If you are already seeing him, you have just been handed next weekend.
What does your dream house have that no normal house does?
Why ask it
It lets a grown guy plan a treehouse again, and the answers run to slides, a secret door behind a bookcase and a room that is only for snacks. Add a room of your own design and see whether he gives it a good spot.
Sunrise or stars: which would you rather get up or stay up for?
Why ask it
A this-or-that with a picture attached. Star people will tell you about one specific night on one specific roof or field. If you are already seeing each other, either answer is easy to actually do, and it costs nothing but an alarm or a blanket.
If you opened a little shop that sold only one thing, what would it sell?
Why ask it
Small dreams are cuter than big ones. Pancakes, repaired bikes, houseplants, exactly one kind of sandwich. Ask what the shop is called and whether you can have a job there; a guy who hires you on the spot and gives you a title is enjoying himself.
Where would you build a blanket fort, and what's allowed inside?
Why ask it
The rules are the fun, so argue about them: whether phones are allowed in, who is in charge of snacks, how many movies fit in one night. With someone you are seeing, this is most of the way to a real plan for a rainy evening.
If you could eat one meal anywhere on earth tomorrow, where and what?
Why ask it
A travel daydream and a favorite food in one. Noodles in Tokyo, his aunt's kitchen, a taco stand he found on vacation and has never stopped talking about. Ask who is across the table: he might say you and he might say his grandfather, and both are good to hear.
If you had a boat, a cabin or a camper van, which one and where would it be?
Why ask it
Three ways of running off for a weekend. Lake people, woods people and road people are different kinds of daydreamer, and he will know at once which he is. Ask what he would name it, because boats have to have names and vans deserve them.
What's a tiny dream you have, something small you'd just love to do someday?
Why ask it
Tiny dreams are things like seeing snow, owning a decent record player or learning one song on guitar. They are easier to say out loud than life goals, which is why this works on a guy you have only known a few weeks. Trade him one of yours before he can feel silly about his.
What kind of old man do you think you'll be?
Why ask it
It looks at the future with no pressure in it, because nobody is being asked about plans. He will pick a type, the grumpy one on the porch or the grandpa with candy in his pocket, and probably do the voice. Keep 'and where am I?' to yourself unless you have been together a good while.
If you could keep one day of your life in a jar to open again, which day?
Why ask it
A sweeter way to ask about his best day, and one that needs a minute of quiet. The days people choose are often ordinary: a beach with cousins, a long drive with his dad. Why he chose it is worth more than the day itself, so ask.
What would you wish for on a shooting star tonight?
Why ask it
He may say he cannot tell you or it will not come true, which is the right answer and a charming one. Do not dig. If he does tell you, be gentle with it, since people sometimes put real wishes inside joke-sized questions.
Goodnight texts
On a scale of wide awake to already dreaming, where are you?
Why ask it
A check on whether to keep talking or let him go. 'Halfway gone' means say goodnight now, kindly, and do not take a slow reply personally. 'Wide awake' means you can borrow one more question from the Daydreams group.
Before you fall asleep: what was the best five minutes of your day?
Why ask it
'Five minutes' gets you a moment and not a summary. As a last text it sends him to bed thinking about something good, with you attached to it. Tell him yours in one line and say goodnight; this one should not turn into an hour.
What's one thing you're looking forward to tomorrow?
Why ask it
It points him at the next day, and a small answer like a good lunch is fine. Check in about it afterward ('how was the famous burrito?'), since being remembered is most of what makes somebody feel liked.
Are you a fall-asleep-instantly person or a stare-at-the-ceiling person?
Why ask it
Ceiling-starers tend to text late, which may explain some of his reply times. Ask what goes through his head up there. If he claims to be out in thirty seconds, tell him you are jealous and let him prove it.
What's the last thing you do before you turn the light off?
Why ask it
A peek at his routine without being nosy: a chapter of a book, one more video, checking that the dog is on the bed. If the honest answer is 'text you', he will probably say so, and you can stop wondering.
How many pillows do you sleep with, and is that the right number?
Why ask it
Completely pointless, which is what the end of the day is for. People have strong feelings here. One-pillow guys and five-pillow guys will both defend themselves, and it is a cozy argument to fall asleep on.
What song should I fall asleep to tonight?
Why ask it
He can answer with a link and no words, which suits a sleepy guy. Play it, and tell him in the morning what you thought. He picked it with you in mind, so even a strange choice says something.
What's the strangest dream you've had lately?
Why ask it
Send it late, when dreams are on topic. Dream stories ramble, so expect several messages in a row. Nothing needs interpreting: 'why was your teacher a duck?' is the correct level of analysis.
What are you hoping to dream about tonight?
Why ask it
Softer than asking to be in his dreams. He can say flying, or pizza, or 'you'll find out tomorrow'. Reply with 'report back in the morning' and tomorrow's first message is already set up.
Can I tell you one thing I liked about today?
Why ask it
He will say yes, so have the thing ready, and make it about him if you can: 'you saved me a seat', 'that joke in math'. It is a compliment with a doorbell on it, which gives a shy guy a second to brace. Bolder than it looks, so wait until you are fairly sure he likes hearing from you.
What should I ask you tomorrow?
Why ask it
He hands you tomorrow's opening line and gets all night to wonder how you will use it. Guys often pick something they have been wanting to tell you. Ask it word for word in the morning.
Do you want a good morning text tomorrow, or would that wake you up?
Why ask it
Asking first is cuter than just sending one, and it finds out when he gets up. A yes is a small standing invitation. Keep the morning message short, because nobody wants a paragraph before breakfast.
Goodnight. Same time tomorrow?
Why ask it
Hardly a question, and the sweetest one here for a thread that has become a nightly thing. It says you liked today and expect another like it. Send it only once the habit exists; on day two of texting it assumes too much.
How to ask a cute question so it stays cute
Practical guidance for the conversation itself
What makes a question cute
Small and specific beats clever
A cute question asks for something little: the name of a stuffed animal, a good-mood song, the rules of a blanket fort. He can answer in a sentence, nothing rides on it, and it works said plainly. If a line needs a wink or a setup to land, it belongs on a flirty list.
He should feel liked, not examined
The test is how he feels after answering. 'What were you scared of as a kid that seems funny now?' leaves him laughing at a six-year-old. 'What's your biggest fear?' leaves him feeling studied. Between two versions of a question, pick the one that gets a story and a smile.
Trade answers
Every question on this page can be turned around, and it should be. Tell him your cartoon, your comfort movie, what you would sell in your one-thing shop. Five sweet questions in a row with nothing given back is still a quiz.
One or two at a time
These are for dropping into a conversation that is already going: at lunch, on a walk, in a thread about homework. One or two in an evening is plenty. If you read them off the page one after another he will notice, and the charm goes with it.
Which group to use when
A crush you have hardly talked to
Stay in Easy and sweet and When he was little. Nothing there mentions the two of you, so a guy who is only being friendly can answer without feeling cornered, and a guy who likes you gets an easy way to keep talking.
A guy who is friendly back
Once he is asking you things too, His soft side and Daydreams open up. They ask for a little more of him, a movie that made him tear up or the day he would keep in a jar, so they suit a quieter moment with nobody else listening.
Someone you have just started seeing
About you two is written for this stage. The group starts with a handshake and a nickname, which are safe with a friend, and ends with how he would describe you to his mom, which is not. Go down it only as far as things have actually gone.
Too much too soon
A question is too soon when it only makes sense if he already likes you. Asking what he noticed about you first, in the first week of talking, leaves him to invent a compliment or dodge. The notes flag the ones to hold back. When unsure, ask the version that is about him and leave yourself out of it.
What to say back
React before you move on
The reply matters more than the question. Laugh, say 'wait, really?', ask one thing about what he just told you. Going straight to the next question tells him the answer was not the point.
Never tease a soft answer
If he tells you about the blanket he slept with until he was nine or the movie that made him cry, that was a small act of trust. Smiling at it is fine. Turning it into a joke later, or in front of his friends, teaches him to give you the safe answer next time.
Keep one detail and bring it back
The treat he wants after a rough day, his good-mood song, the tiny dream. Pick one thing per conversation to remember, and use it a week or two later: the snack on a bad Tuesday, the song sent with no message. That does more than any question on the list.
When he gives you a short answer
A one-word reply usually means the question caught him off guard or the timing was off. Answer it yourself in a line, which shows him the size of answer you had in mind, and carry on with something ordinary. If short answers are all you get over a couple of weeks, ease off and let him come to you.
Sending one as a goodnight text
One question, then goodnight
A goodnight text should be easy to answer with his eyes half closed. Send one question, enjoy the reply, tell him yours in a line and say goodnight. The Daydreams group is there for the nights he says he is wide awake.
Send it while he is still up
Aim for the hour he usually goes quiet, not long after it. A question that arrives at one in the morning reads as a different kind of message, and it may wake him. If he answers at breakfast, that is still an answer, and a nice start to the day's thread.
Let an unanswered one rest
If last night's question got no reply, do not send another on top of it. He fell asleep, or his phone was in another room. Wait for him to pick the thread back up, and if a day or two passes without that, slow down.
Not every night straight away
A goodnight text every single night is a habit for two people who are already seeing each other. With a crush, two or three a week keeps it a nice surprise. 'Goodnight. Same time tomorrow?' sits at the bottom of the group for a reason: it belongs to a thread that already runs most nights.