Flirty Questions to Ask a Guy
Flirty questions to ask a guy you like, whether he is standing next to you or at the other end of a text thread: playful, cute and complimentary, and never more than that. The 93 questions run from gentle to bold across six groups: Playful openers, Compliments in disguise, Funny and flirty, Over text, Is he interested and Getting bolder. Each one has a note on how to say it and how to read what he says back.
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The questions
Each question, and why to ask it
Playful openers
Do you smile at everyone like that, or should I feel special?
Why ask it
Ask it the second you catch the smile, while it is still on his face. 'Everyone' said with a grin is him teasing you back, and 'just you' is the answer you were fishing for. Whichever you get, smile back and let him be the next one to speak.
On a scale of one to ten, how much trouble are you?
Why ask it
Ask it with a half smile so he knows a serious answer is not wanted. A guy who claims a ten is playing along, and so is the one who says 'a two, I'm very well behaved', because the only reply to that is 'I don't believe you'.
Were you planning to say hi, or was I always going to have to do it?
Why ask it
For the guy you keep trading looks with across a classroom or a party. It teases him for waiting and tells him the looks were noticed. 'I was working up to it' is as good as a confession.
Are you a good idea or a bad idea?
Why ask it
Short enough to say in passing, and there is no wrong reply. 'Bad idea' with a grin is about the flirtiest thing he can say back. Should he ask which one you were hoping for, he has taken over the game, so answer him.
What's your excuse for being this distracting?
Why ask it
Works best when you really are meant to be doing something else, like studying or working a shift beside him. Keep your eyes on your notes when you say it. An apology with a grin, followed by him carrying on exactly as before, means he liked hearing it.
Is this seat free, or are you saving it for someone more interesting?
Why ask it
Start sitting down as you ask, so the question is clearly a joke. You are fishing for 'nobody more interesting than you', and plenty of guys will supply it. When the seat really is taken, 'my loss' and a smile is all you need.
Are you shy, or are you being mysterious on purpose?
Why ask it
Meant for the quiet one at the edge of the group. Both options flatter him, which makes it far easier to answer than 'why are you so quiet?'. A shy guy can take 'mysterious' and run with it, and then he has a character to play for the rest of the conversation.
Do you want to hear my first impression of you, or would you rather not know?
Why ask it
Hardly anyone turns this down, so have a real answer ready that is half tease and half compliment: 'I thought you were too cool to talk to, and then you tripped over a chair.' Once you have told him, he owes you his first impression of you.
Which of us do you think is the worse influence?
Why ask it
It puts the two of you on a team before anything has happened. Whoever he names, disagree, and you have a playful argument that can run all evening. 'You, obviously' is worth noticing: blaming you is a way of saying you get to him.
How have we gone this long without really talking?
Why ask it
Good for someone you have known by sight for months: a classmate, a coworker, a friend of a friend. It says you wish you had started sooner without quite saying it. Notice whether he blames himself, blames you or suggests making up for lost time.
If I dared you to do something right now, would you say yes before hearing what it is?
Why ask it
You are finding out how much he trusts you and how much he likes a game. Have a small dare ready, such as swapping seats or showing you the last photo he took, because a yes with nothing behind it falls flat. Keep the dare to something he could do in front of a teacher.
What would I have to do to steal you from your friends for five minutes?
Why ask it
Say it quietly at a party or a lunch table, to him and not to the whole group. Standing up on the spot is the best answer he can give. Some guys will name a price, like a snack or the next dance, and paying it is half the fun.
You have ten seconds: what's the most interesting thing about you?
Why ask it
Count down out loud on your fingers, because the time pressure is the fun of it. Panic answers are better than polished ones. Whatever he blurts out, ask for the full story once the clock stops.
Is your day going well, or do you need me to rescue it?
Why ask it
An ordinary 'how's your day' with an offer attached. Have a small rescue in mind in case he takes you up on it: a snack from the vending machine, a walk to his next class, a terrible joke. A good day needs no rescue, so ask what made it good instead.
Where did the last hour go, and why is that always your fault?
Why ask it
It belongs at the end of a long conversation, when one of you has just noticed the time. Blaming him is the compliment, because you are telling him the hour flew. He may blame you straight back, which is the same compliment returned.
Compliments in disguise
Can you laugh like that again? I wasn't ready the first time.
Why ask it
Say it straight after a real laugh, the kind he did not plan. Praising his laugh is more personal than praising something he did, so expect a second of surprise. He probably cannot laugh on command, and trying to will set him off again.
What's the catch with you? There has to be one.
Why ask it
The compliment is in the suspicion: you are saying he seems too good so far. He will list his flaws to prove he is normal, and they tend to be funny ones, like dancing, parallel parking or replying on time. Pick one and offer to judge it in person.
Do you plan your jokes in advance, or are you really this quick?
Why ask it
Wait until he has made you laugh twice in a minute. He may credit a brother, a favorite show or years of being the smallest kid in class. A guy who suddenly cannot think of anything funny to say has been flattered.
Does your hair just do that, or is there a whole routine I don't know about?
Why ask it
Light enough for someone you barely know, and it lets him know you have been looking. Tease him about the routine if he admits to one. A claim that it is all natural should be met with open disbelief.
Why does everything sound more interesting when you explain it?
Why ask it
Use it after he has gone on about something he loves, like a game, an engine or a band. It rewards him for talking instead of making him self-conscious about it. Do not be surprised if he explains something else to you within the hour.
Did you know you get a certain look when you talk about something you love?
Why ask it
He will ask 'what look?', and then you get to describe it. Keep the description kind and specific, such as the way he talks faster or starts using his hands. You are telling him you watch him when he is not performing, which flatters more quietly than a remark about his looks.
Do you practice being this charming, or is it an accident?
Why ask it
Keep it for a moment when he has done something smooth, such as holding a door or remembering your order. 'Accident' is modest and 'hours of practice' is him joking back. A blank look means he did not know he was being charming, which is sweeter.
How are you this calm about everything? I need lessons.
Why ask it
For the guy who stays steady when a plan falls apart or a test goes badly. Asking for lessons turns the compliment into something he can offer you. 'I'm not calm at all, I just hide it' is a small true thing about himself, so do not joke past it.
Do your eyes always do that when you smile?
Why ask it
Bolder than it reads, because it makes plain you have been looking at his face. Say it quietly and one to one, never in front of his friends. He will probably ask 'do what?', and you can leave that unanswered with a shrug.
Can you say my name again? I like how it sounds when you say it.
Why ask it
It compliments his voice while asking for almost nothing. Use it right after he has said your name, and keep your own voice low and unhurried. He will probably say it again with a laugh, and you can listen for whether your name turns up in his sentences more often afterward.
How long did it take you to get that good? I was watching the whole time.
Why ask it
Ask after you have watched him play, draw, cook, skate or fix something. Admiring a skill he worked for goes deeper than praising his looks, and the second sentence admits you could not look away. Listen for how many years he has been at it, then ask to see more.
Who raised you to be this polite? I'd like to send a thank-you card.
Why ask it
This one is about character, so use it when you have seen him be kind to a waiter, a younger kid or someone left out. He will probably name a parent or a grandparent. It is flirting he could repeat to his mother, which makes it safe to say with other people in earshot.
Do you have any idea how easy you make it to be around you?
Why ask it
Almost a straight compliment, with a question mark to give him something to answer. Good for the quiet guy who thinks he is boring company. 'Only with you' in reply means the flirting has become mutual.
What is that cologne, and are you aware it's unfair?
Why ask it
Fine at close range, a little odd if called across a table. He will likely tell you the name. Whether he has it on the next time he knows he will see you is worth a quiet look.
Do your friends know you're the reason the group photos look good?
Why ask it
The most direct line in this group, softened by how over the top it is. Deliver it deadpan while you are both looking at an actual photo. Watch how he deflects: 'you've clearly not seen the ones you're in' is him returning the favor.
Funny and flirty
How many of my bad jokes can you take before you walk away?
Why ask it
Follow it with a truly awful pun so he has something to judge. A guy who groans and stays is enjoying himself. One who answers with a worse joke of his own has matched your level, so keep going.
If we got stuck in an elevator, which of us would get annoying first?
Why ask it
He will say you, you will say him, and the back and forth is the point. Push it further by asking what his survival plan is. A plan that includes keeping you entertained is flirting.
What's our team name if we enter a trivia night together?
Why ask it
You are asking him to invent something that belongs to the two of you. A fast, silly answer shows he likes the idea of being a pair. Keep the name: bringing it up a week later is an inside joke ready made.
Who's your celebrity crush, and should I be worried?
Why ask it
The first half is the question everybody asks, and the second half is the flirt. 'Very worried' is a tease, and 'not at all' is a compliment he may not realize he is paying. Tell him yours afterward, since fair is fair.
Want to hear the worst pickup line I know and give it a score?
Why ask it
Pickup lines are an easy way in, because the two of you get to laugh at flirting while doing it. The more groan-worthy the line, the better this works. Take your score out of ten, then demand he beat it with one of his own.
If we were in a movie, is this the part where we can't stand each other or the part where we figure it out?
Why ask it
Best with a guy you bicker with for fun. It names what every rivals-to-something-more plot is about without making you say it. Give him a second after 'figure it out', because he may have surprised himself.
In a staring contest, which of us blinks first and which of us laughs first?
Why ask it
Do not wait for the answer. Start the contest. Ten seconds of eye contact with a reason attached is easier than ten seconds without one, and whoever laughs first has lost in the nicest possible way.
Would you let me win at mini golf, or would I have to earn it?
Why ask it
A date idea wearing a joke. 'Earn it' means he is competitive and wants you to try. 'Let you win' is gallant, so tell him you would know and be insulted, and then name a day.
If we had to turn up to a costume party as a pair, what are we going as?
Why ask it
Pairs come with built-in meaning, so listen to what he reaches for: two rivals, a famous duo, a couple. Argue over who gets the better half. With a real party coming up, this stops being hypothetical.
How long would we last in a silent library before one of us got us thrown out?
Why ask it
Works on a study partner or anyone you whisper with when you should not. Any answer under ten minutes is him admitting you make each other laugh at the wrong moments. Ask who the librarian would blame, and expect him to say you.
If I baked you cookies and they were awful, would you eat them anyway?
Why ask it
A small test of whether he would put being kind to you ahead of being honest with you. 'Every last one' is the sweet answer, and 'I'd tell you gently' is a good one too. Whichever you get, you now have an excuse to bake.
Which of us would get us lost first on a road trip?
Why ask it
It pictures hours in a car together and treats that as normal. Follow up with who controls the music and who is in charge of snacks. A guy who starts assigning jobs is already on the trip.
What do I get for putting up with your taste in music?
Why ask it
Only fair if you have heard his music, so ask after he has made you listen to something. He will defend the song and then name a reward, often food. Hold him to it.
What nickname would you give me if you had to pick one right now?
Why ask it
Being given a nickname is a small claim on you, which is why this feels flirty. Putting him on the spot gets a sillier answer than giving him a day to think. Veto the first one on principle, and answer to the second.
Would you share your umbrella with me, or watch me get soaked and laugh?
Why ask it
On the cute end of flirty, and good for a gray day when it could come true by three o'clock. Sharing is the gentleman's answer. 'Laugh first, then share' is the honest one from a guy who is comfortable teasing you.
Over text
Did you smile when my name popped up just now? Be honest.
Why ask it
An opener for a thread that is already friendly, sent as the first message of the day. 'Maybe' usually leans toward yes. Expect the question to come straight back, and tell the truth when it does, since you started it.
Bored yet, or am I still the best thing on your phone?
Why ask it
Send it in the middle of a long back-and-forth, not at the start of one. It jokes about being a nuisance while assuming you are not one. Should he name a game or an app as your rival, declare war on it.
Guess what I'm thinking about. I'll tell you when you're getting warm.
Why ask it
A game gives him a reason to send several messages instead of one. Have a real answer ready, something light like pizza or the joke he made yesterday. A first guess of 'me' means he is hoping to be right.
Should I be flattered that you replied that fast?
Why ask it
Send it only when he has replied within a minute, and only once. 'Yes' is a clear signal, and 'I was already on my phone' is a guy protecting his pride.
What's my contact name in your phone? I want to know if I've earned an emoji yet.
Why ask it
He can check in two seconds, so you will get a quick reply. First name only means nothing yet. A nickname or an emoji means he has thought about it, and a screenshot as evidence is a bonus.
What would it take to get a voice note from you? I've forgotten what you sound like.
Why ask it
It asks for more of him without asking for a photo, which keeps it comfortable. Some guys hate recording themselves, so let a refusal go. When one does arrive, answer with one of your own instead of typing.
What was the last thing that made you think of me?
Why ask it
The flirty text everyone expects on a list like this, and it earns its place because he has to produce a specific moment. A song, a joke or a sandwich all count. 'Nothing yet today' can be a tease, so read it next to everything else he sends.
Good morning. Did I make your first five thoughts today?
Why ask it
Send it before his day gets busy, since a question gives him more to answer than a plain good morning. 'Top three' is him flirting. A sleepy 'morning' with nothing else is just a guy who is not awake yet.
I bet I can make you smile in three texts. Want to start the clock?
Why ask it
Now you have to deliver, so line up the three before you send this: a photo of something ridiculous, an inside joke, one honest compliment. Losing is fine. 'Nope, try again' is him asking for three more.
Rate my last text out of ten. I thought it was pretty smooth.
Why ask it
Use it after a line of yours that was a bit much, to show you can laugh at yourself. A harsh score with a laughing emoji is affection. A ten means he is being kind or is completely gone, and both are good news.
Whose turn is it to text first tomorrow, yours or mine?
Why ask it
Send it as a goodnight message, so tomorrow is settled before today is over. 'Mine' is a promise, and you get to see whether he keeps it. Who starts the conversations over a week tells you a lot, which makes this worth asking even as a joke.
If we were hanging out right now instead of texting, where would we be?
Why ask it
It keeps the daydream to a place: a diner booth, a bench at the park, the arcade. Whatever he pictures is a date he would say yes to, so save the answer. A place close by deserves one more text from you: 'when?'
Finish this sentence for me: 'I was hoping you'd ask me...'
Why ask it
He gets to pick the question he wants, so the answer can be a joke or a real hint. Give the three dots a minute. Then ask him whatever he wrote, word for word.
Is there a me-shaped gap in your weekend, or is it fully booked?
Why ask it
Send it by Thursday so there is still time for him to make room. It is an invitation he can accept without either of you saying 'date'. Busy but interested sounds like 'not Saturday, how about Sunday?', and a plain 'booked' with no other day offered is its own answer.
Would you rather keep texting or hear the rest of this in person?
Why ask it
Start a story, stop halfway and send this. It moves the conversation off the phone, where a smile can do the work an emoji cannot. A vote for texting is not a disaster: finish the story and try again another week.
Sweet dreams. Any chance I'm in them?
Why ask it
Cheesy on purpose, and the cheese is what makes it safe: he can laugh at it or play along. Send it as your final message so he does not have to answer until morning. A reply that same night is a good sign.
Is he interested
What makes you look twice at someone?
Why ask it
General enough to ask early, and personal enough to be useful. Listen for whether he lists looks or something like a laugh or confidence. When part of it sounds like you, he may be choosing his words on purpose.
What kind of date would you be most excited to be asked on?
Why ask it
Listen to how much detail he gives: a full plan suggests he has pictured one lately. Notice whether it fits things he knows you like, and say which part of it you would enjoy.
Do you get quieter or louder around someone you like?
Why ask it
Guys split both ways on this, and you may have been misreading him. Compare the answer with how he acts around you. A quiet guy who says 'quieter' has possibly just explained the last month.
How do you feel when the other person makes the first move?
Why ask it
Asking tells him you are the kind of person who might. Relief is a common answer, since going first is the part a lot of people dread. A guy who says he prefers to do it himself needs a clear opening, so give him one and see.
What was the first thing you noticed about me? You're not allowed to say my shoes.
Why ask it
Ruling out a joke answer nudges him toward a real one. A detail from before you two had ever spoken, such as where you were sitting or what you were laughing at, means he noticed you earlier than he let on. Have your answer about him ready, because he will ask.
If I went quiet for a week, would you notice by day two or day five?
Why ask it
Underneath the joke, you are asking whether you are part of his routine. 'Day one' is the best answer available. A crack about enjoying the peace is still engagement, but notice when jokes are all you ever get.
Do you remember the first thing I ever said to you?
Why ask it
Getting it right, or even close, means the moment stuck. No idea at all is common and proves nothing, so tell him, and make the story funny instead of making him feel bad.
What's the nicest thing you've done for someone you liked?
Why ask it
Shows you what his effort looks like when he is interested: a long drive, a saved seat, a song learned on guitar. Compare it, privately, with anything he has done for you. Small versions of the same thing count.
What do you do when you like someone and can't tell if they like you back?
Why ask it
This is your own situation handed to him as a question. Some guys wait, some test with jokes, some ask a friend to find out. Whatever he describes, check whether he has been doing it with you.
Are you good at taking hints, or do you need things spelled out?
Why ask it
Treat the answer as instructions. 'Spell it out' means your hints may have been going over his head, and you can stop hinting. 'I notice everything' from a guy who has not reacted to yours is either a bluff or an answer, and the next week will show which.
What's the longest you've liked someone without saying a word?
Why ask it
A number in months tells you he is patient with a crush, and a guy like that may never show his hand first. Ask what finally made him say something, or what stopped him.
What would someone have to do to really impress you?
Why ask it
You are asking for the cheat sheet and he knows it. Food, laughing at his jokes and being nice to his dog are common entries. Do one of them within the week, and see whether he notices that you listened.
Is there anyone you're hoping will text you tonight?
Why ask it
Light, a little nosy, and best asked by text for obvious reasons. 'You already did' is the reply you are after. A name that is not yours stings, but it saves you weeks of guessing.
If I asked your best friend whether you're single, what would they say?
Why ask it
The detour through the friend makes a blunt question funny, and it is one you need answered before going any further. Take 'it's complicated' at its word and ease off.
If I invited you somewhere and you didn't know anyone else going, would you still come?
Why ask it
Turning up for you alone is the whole point of the question. 'Depends what it is' is fair, so have a real thing in mind: a friend's birthday, a school play, a game. Give a yes the day and the time before he can think twice.
Getting bolder
Should I stop flirting with you, or is it working?
Why ask it
Admits what you have been doing and asks for a progress report. People rarely say 'stop' to this unless they mean it, so take a stop at face value. 'Keep going' tends to come with a red face.
Be honest: cute, funny or trouble. Which one am I?
Why ask it
A safer cousin of 'do you think I'm cute', because every option is a compliment. 'All three' is the smooth reply. A vote for 'trouble' deserves a follow-up: ask what you did, and enjoy the list.
Do you have a type, and am I anywhere near it?
Why ask it
The second half is the bold part, so say it lightly and be ready to hear the answer. An interested guy tends to describe someone suspiciously like you. A type that sounds nothing like you gets a shrug and 'do types ever turn out to be right?'
What's something you like about me that you haven't said out loud?
Why ask it
It assumes there is something, which is a confident thing to assume. Give him time, since sincere compliments come slower than jokes. Thank him without brushing it off, then tell him one about himself.
Do you ever think about me when we're not talking?
Why ask it
Better by text or on a walk than face to face across a table, where it can feel like a spotlight. 'Sometimes' from a shy guy is a big admission. Tell him when you think about him, with one real example.
Have you ever thought about us as more than friends?
Why ask it
For a friendship that has been drifting toward something else. Ask only if you could cope with either answer, because it cannot be unsaid. A long pause is not a no: it may just be him deciding how honest to be.
Do you think we'd be a good couple, or would we drive each other up the wall?
Why ask it
The joke half gives him cover to consider the serious half. 'Both' is the reply of a guy who has pictured it. A list of reasons you would be good together was probably not written on the spot.
If I said I had a crush on you, would that be good news?
Why ask it
A confession with the word 'if' in front of it, so you can still call it a hypothetical. His face will answer before he does. Good news means you can drop the 'if'.
What would you do if I took your hand right now?
Why ask it
Ask it quietly while you are walking side by side. 'Hold on' and 'find out' are both invitations. Hesitation or a laugh means keep your hands in your pockets and change the subject without any fuss.
If I rested my head on your shoulder during a movie, would you move?
Why ask it
Small, sweet and easy to picture, which makes it a gentle way to ask about being close. 'I'd stay very still' is the classic nervous answer and a good one. It also proposes a movie.
If a slow song came on right now, would you ask me to dance or suddenly need to check your phone?
Why ask it
Made for a school dance, a wedding or a kitchen with the radio on. The phone option lets a shy guy laugh at himself. With music actually playing, hold out a hand and settle it.
What would you say if I asked you to walk me home?
Why ask it
Keep this one for a guy you already know and trust, like a classmate or a friend, and not someone you met that night. It is a small, old-fashioned request that buys you fifteen unhurried minutes together. An offer from a guy who lives in the opposite direction is worth noticing.
Are you a kiss-on-the-first-date person, or do you like to wait?
Why ask it
As bold as this page gets, and it asks for his opinion; it is not an offer. Keep it for when the flirting is clearly going both ways. Should he ask which you prefer, say so or just smile, and change the subject if the mood turns into something you do not like.
So, when are you going to ask for my number?
Why ask it
For someone you have just met and do not want to lose track of. Say it as you are getting ready to leave, so he has to act. Handing him your phone with a new contact open removes his last excuse.
What's stopping you from asking me out?
Why ask it
Use it when you are fairly sure he likes you and nothing is happening. The honest answers are usually nerves or not being sure of you, and both are fixed by telling him you would say yes. Any other reason is one you want to know.
Is it too soon to say I'd like to see you again?
Why ask it
Say it at the end of a good first hangout, before the goodbye gets awkward. It is honest, it is kind, and it saves you both two days of wondering. 'Not too soon' should be followed by a day of the week.
Do you know anyone funny, free on Friday and currently standing in front of me?
Why ask it
An invitation built as a joke, for when you have something to invite him to: a dance, a game, a birthday. He only has to say 'I might know a guy'. Have the time and place ready, because the next thing he asks will be where.
How to flirt with questions without overdoing it
Practical guidance for the conversation itself
Making a flirty question land
Tone does half the work
Read flat, 'what's your excuse for being this distracting?' is a complaint. Said with a small smile and a lighter voice it is a compliment. If you cannot say a question without cringing, pick a different one: he will hear the cringe before he hears the words.
One flirty line, then a normal one
Flirting works by contrast. Drop one of these into an ordinary conversation about school, work or the game last night, then go back to the ordinary conversation. Three in a row stops being a spark and starts being a routine he has to keep up with.
Have your own answer ready
Nearly every question here can be turned around, and a guy who is enjoying himself will do exactly that. Decide beforehand how much trouble you are out of ten and what you would do in a staring contest. Freezing on your own question takes the air out of it.
Work down each group, and earn the last one
Every group starts gentle and ends bolder. Playful openers and Compliments in disguise are safe with someone you hardly know. Getting bolder is for a guy who has already flirted back at least once, because those questions ask him to say something real, and the last few of them are invitations, so have a day or a plan in mind before you ask.
Pacing it over text
Match his rhythm, roughly
If he answers in a few lines an hour later, a wall of text thirty seconds after that is a lot to receive. You do not need to count minutes or wait on purpose. Just keep your messages about as long and about as frequent as his, and let the pace pick up when he picks it up.
One flirty question a day is plenty
Send one, enjoy the reply, and let the rest of the day's messages be normal. A thread where every line is a tease gives him nothing to relax into, and the question that would have made him grin on Monday is noise by Thursday.
Make the tone visible
Text removes your face, so a tease can read as a dig. A 'be honest', an emoji or a joke at your own expense shows him which way to take it. Before sending, read the message as if it came from someone you barely know. If it could sound cold or pushy, soften it.
Never flirt into a silence
A flirty line sent after a message he has not answered yet asks him for two replies at once, and it starts to feel like being chased. Wait until he has answered, even if that is tomorrow. If two messages in a row go unanswered, stop there and let the next one come from him.
Use the phone to get off the phone
Texting keeps things warm between the times you see him. It is a poor place to find out whether he likes you, because the looks and the pauses are missing. The last few Over text questions, about where you would be hanging out, the gap in his weekend and hearing the rest in person, exist to turn a good thread into a plan.
Reading his reply
What flirting back looks like
He turns the question around on you, makes the joke bigger, teases you about your answer, or brings the line up again days later. A longer reply than the question needed is a sign too. Any one of these means carry on.
What polite looks like
He answers the literal question and stops. A 'haha' and a change of subject, no question back, the same friendly tone he uses with everyone. One reply like that tells you very little. The same reply to three different questions tells you a good deal.
Shy is not the same as uninterested
Some guys go red, go quiet or make a clumsy joke when someone flirts with them, and it can pass for a brush-off. Look at what he does next. A shy guy who likes you stays nearby, keeps the conversation alive some other way, and often comes back with an answer an hour later.
Watch what he does, not only what he says
Words in the moment are easy. Whether he messages first sometimes, remembers what you told him and makes time to see you is harder to fake. Good banter with none of that behind it is fun, and you should take it as fun and nothing more.
When he does not flirt back
Step down one level and keep talking
If a line lands flat, do not explain it or apologize for it. Say 'well, I thought it was funny', laugh, and ask him something ordinary. Going back to friendly conversation without a wobble keeps things comfortable for both of you and leaves the door open.
Give it one more try on another day
A flat reply can be about his day, the friends standing next to him or an exam in the morning. Try once more later in the week, somewhere quieter, with a question from the top of a group. Change the setting, not the volume: going bolder to force a reaction rarely gets the one you want.
Believe a pattern
If two or three gentle tries over a couple of weeks all get kind, level replies, he has answered you. He does not owe you a reason, and you have not done anything wrong by asking. Dropping the flirting and staying friendly is the move that lets you both keep the friendship.
When he says no, or is seeing someone
If he tells you he is not interested, asks you to stop or mentions a girlfriend or boyfriend, stop flirting completely. 'No worries, thanks for telling me' is all it needs. Carrying on after a clear answer is no longer playful, and it puts him in a spot he did not ask to be in.