Flirty Questions to Ask Your Boyfriend
Flirty questions to ask your boyfriend, for when you've been together a while and want the early butterflies back for an evening, over text or on a night in. The 50 questions are grouped in the order a flirty conversation tends to go: teasing first, then compliments, how the two of you started and date nights, a group written for texting, and a few bolder ones to finish, all of them playful and none explicit.
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The questions
Each question, and why to ask it
Teasing
Who is the bigger flirt out of the two of us, and what's your evidence?
Why ask it
Asking for evidence is what makes it a game: he has to bring up a specific time you flirted with him, which is a compliment in disguise. If he names himself, ask for a demonstration. Either verdict gives you an excuse to prove him wrong on the spot.
Do you still get a little nervous around me, or has that worn off completely?
Why ask it
'Only when you look at me like that' is the answer to hope for, and a flat 'no' is usually comfort, not boredom. Follow up by asking when the nerves were worst, which tends to bring out a story from your first weeks that you haven't heard.
What do I do that distracts you most when you're supposed to be concentrating?
Why ask it
Best asked while he is in the middle of something small, like a game or a recipe, never real work with a deadline. Whatever he names, do it once more and then leave him alone. A shrug here mostly means bad timing, so save it for later.
If I flirted with you tonight like we'd only just met, would you play along or laugh at me?
Why ask it
A set-up more than a question: if he says he would play along, start right away with 'so, do you come here often' on your own couch. Laughing is fine as long as he joins in after. It suits couples who have slid into talking mostly about errands.
Do you think you can still make me blush? You have one try.
Why ask it
A dare, so only ask when you're ready to lose. He will either say something very sweet or something ridiculous, and both count. If he actually manages it, admit it: a boyfriend who learns his effort lands will try again.
Which of my nicknames for you do you secretly like, and which one do you just put up with?
Why ask it
Listen for the name he would never admit to liking in front of his friends. If he says he only puts up with 'babe', invent three worse ones on the spot and make him choose. The secret favorite stays between the two of you unless he says otherwise.
What would you do if I stole your hoodie and never gave it back?
Why ask it
Wear the hoodie while you ask, or send the question with a photo of the evidence. 'Keep it, it looks better on you' is as flirty as answers get. A list of demands for its return is him playing, so negotiate badly on purpose.
Am I more trouble than you expected when you signed up for this?
Why ask it
Say it right after you've done something mildly annoying, like eating the last of his fries. He's meant to agree and then add that he'd sign up again, so prompt him if he forgets the second half. Skip it during a real rough patch, when 'trouble' may get an honest answer you weren't ready for.
What's the cheesiest line you'd use on me if you had to win me over again tonight?
Why ask it
Guys who claim to hate pickup lines usually know three. Score it out of ten, groan loudly, and then let it work anyway. If he blanks, offer your own worst one first so the bar is on the floor.
Compliments
What's your favorite thing about me today? It's allowed to change tomorrow.
Why ask it
'Today' is what keeps it light: he isn't ranking your whole personality, only saying what he noticed since this morning. 'Everything' is a dodge, so ask for one thing, and expect something like the way you sang in the car. Ask again next week and compare.
What was I wearing the last time you couldn't stop looking at me?
Why ask it
It asks him for one picture from memory, not a ranking of your wardrobe. He may be vague on clothes, so 'the green thing' is a real answer and worth a laugh. Then wear the green thing on your next night out and see whether he notices.
My smile or my laugh: which one gets you, if you have to pick?
Why ask it
Forcing a choice between two good things means every answer is a compliment. Ask why, because the reason is the bit you'll remember. An answer like 'your laugh, the real one, not the polite one' comes from someone who has been paying attention for a long time.
What do I do without trying that you find really attractive?
Why ask it
The best answers here are oddly small: the way you tie your hair up, how you talk to waiters, your concentrating face. If what he says surprises you, don't start doing it on purpose or you'll ruin it. Trade him one of his own that he has no idea about.
Want to guess the first thing about you I'd brag about to a friend?
Why ask it
This one is really you paying the compliment, so have the answer ready before you ask. Let him guess twice. His guesses show what he believes you like about him, which is sometimes far off and worth correcting.
Do you know how good you look in that shirt, or is this news to you?
Why ask it
Works only when it's true and only in the moment, so use it the minute he walks in wearing the thing. He might go quiet if he isn't used to hearing it. That quiet is usually pleased, and you may see the shirt a lot more from now on.
What's a compliment you wish I gave you more often?
Why ask it
More sincere than it sounds, so ask it lightly. It could be about his work, his cooking or how he looks, and whatever it is, he has just handed you instructions. Use them within the week, not within the minute, or it sounds like a script.
When do I look my best to you: dressed up for a night out, or in your T-shirt with my hair a mess?
Why ask it
The T-shirt wins more often than you'd expect, and he generally means it. If he picks dressed up, that's your cue to suggest somewhere worth dressing for. Ask on a night in, when you are already wearing the second option.
How we started
What was your first impression of me, and how long did I take to ruin it?
Why ask it
Ask for the first five seconds, before he knew anything about you. 'Loud', 'scary' and 'out of my league' are all worth arguing with, and an impression that still fits means he read you right from the start. Give him yours of him afterward, including the part you got wrong.
Did you know I liked you before I said so, or did I hide it well?
Why ask it
You find out how obvious you were, which is embarrassing in the good way. A boyfriend who says 'I had no idea' was probably just as nervous as you. Follow with the sign you thought was unmissable and watch him realize what he walked past.
Which of us made the first move, really? I want your version on the record.
Why ask it
Two people can remember this very differently, and the disagreement is the fun. State your case like a lawyer and let him state his. Should the two stories match exactly, move on to who took longer to say 'I love you', if you're at that stage.
How long did you spend getting ready for our first date? Be honest.
Why ask it
Changing his shirt twice or cleaning out his car counts as a confession, so reward it with your own number. 'Five minutes' from a guy who turned up looking good deserves some doubt. It works less well if your first date was an accident, in which case ask about the second.
What did you tell your friends about me after our first date?
Why ask it
Ask for the real wording, not the cleaned-up one. 'I told them I was done for' is the dream, but 'I said you were cool' from a guy who plays things down means about the same. If he says he told no one, ask who he wanted to tell.
When did you first want to kiss me, and what stopped you?
Why ask it
Most couples have a gap between the wanting and the first kiss, and his side of that gap is a story you probably haven't heard in full. A precise answer, down to the place, shows how closely he was watching. Tell him when it was for you and see how far apart the two moments were.
What was the moment you thought, 'okay, I'm in trouble with this one'?
Why ask it
'In trouble' lets him talk about falling for you without having to use the word, which helps a guy who gets shy about feelings. The moment he picks is rarely a big one. If he can't find it on the spot, let him come back to it; some of the best answers arrive a day late by text.
What's something small I did in our first month that you still think about?
Why ask it
'Small' steers him away from the anniversary highlights and toward a note, a look or one particular text. Don't be hurt when you have no memory of it; that's the point of asking. Whatever it was can be done again, and doing it this week is the flirtiest follow-up there is.
Date nights
If I'm all yours this Saturday with no plans made, what are we doing?
Why ask it
Name a real day so the answer can turn into a plan. A guy who answers in detail has been wanting to be asked, and 'whatever you want' deserves a gentle 'no, your pick'. Put it in both calendars before the conversation moves on.
Night in: are we cooking together, or ordering food and not leaving the couch?
Why ask it
Either-or keeps it easy when he's tired, and both options end with you next to each other. Cooking together is the more flirtatious choice if you're willing to get in each other's way on purpose. Ask it on the day, around four, while dinner is still undecided.
How would you sweep me off my feet with almost no money to spend?
Why ask it
Removing the budget removes the pressure, and the answers get more personal: a walk somewhere he knows, a playlist, his one good recipe. If the idea is good, call his bluff and ask when. A blank is normal, so offer one of your own to get him started.
Where would you take me if we could disappear for one weekend?
Why ask it
A daydream question, best asked lying around with nowhere to be. Listen for whether he picks somewhere for himself or somewhere he thinks you'd love. Don't turn it into a budget discussion tonight; the planning can wait and the mood can't.
Slow dance in the kitchen: would you actually do it, or would I have to drag you?
Why ask it
Put a song on before you ask, so 'I'd do it' can be tested within seconds. A reluctant dancer who shuffles in a circle with you for one chorus has done something sweeter than a confident one. If he truly hates it, let him off and make him pick the song instead.
You get to pick one thing I wear on our next date. What is it?
Why ask it
One item keeps this sweet: a dress he likes, his jacket, the earrings he bought you. It also tells you what he notices. Should he go blank, narrow it to a color. You keep the right to veto, and you can ask for the same favor back.
If you planned a surprise for me, could you keep it quiet, or would your face give you away?
Why ask it
Half tease about his poker face, half hint that you would enjoy a surprise. 'I could, I've done it before' invites you to ask what you missed. If he takes the hint and something turns up weeks later, don't mention that you asked for it.
Which date of ours would you repeat exactly, same place and same order?
Why ask it
The one he chooses shows what he counts as a great night, which may be much simpler than you'd guess. Offer to redo it, and compare which details each of you has kept. A quick answer here means he has thought about that night since.
Over text
What are you doing right now, and would it be better if I were there?
Why ask it
About the plainest flirty text there is, and it works because the second half has only one good answer. Send it when you know he's doing something dull. If he's busy he'll reply late, and a late 'obviously' still counts.
How distracted are you today out of ten, and how much of that is my fault?
Why ask it
Good for the middle of a workday or a long class, when a number is all he has time to type. Anything above five blamed on you is him flirting back. A 'two, I'm slammed' is honest, so wish him luck and try again in the evening.
Guess which photo of you I just looked at again.
Why ask it
Only send it if there really is a photo, because he will ask to see which one. It tells him you look at pictures of him when he's not around, which he may never have assumed. Send the photo with one line about why you like it.
If I turned up at your door in twenty minutes, what would we do with the evening?
Why ask it
For couples who live apart, and most fun on a night when you could actually do it. Pay attention to how fast the answer comes and whether it includes food. 'I'd need thirty to tidy up' is a yes.
Can I have a selfie of your face right now? I need to check something.
Why ask it
Asking for his face, exactly as it is, keeps this cute and gets you the unposed one with bad lighting. When he asks what you were checking, the answer is 'still cute, thanks'. Send one back so it's a trade, and never pass his along to anyone.
What's the first thing you'll do when you see me next?
Why ask it
A countdown text for the day before you meet up or the last stretch of time apart. Hugs, lifting you off the ground and handing over food are all strong answers. Remember what he says and hold him to it at the door.
Do you miss me yet, or should I stay away a bit longer?
Why ask it
Send it a few hours into time apart, not a few minutes. 'Come back' is the easy win, and 'stay away, I'm enjoying the quiet' is a guy comfortable enough to joke. Don't send it after an argument, when it reads as a test.
Goodnight text or goodnight call: which one do I get tonight?
Why ask it
It assumes you're getting one of them, which is the flirty part. A call when he's tired says a lot. If he picks text, ask for a good one and reply to it in the morning so the thread starts warm.
A little bolder
How long could you go without kissing me before you cracked?
Why ask it
He'll claim a heroic number, and then you get to test it. Set a silly bet on it, with the loser buying the next coffee. It only works as a game if you're prepared to lose it yourself inside the hour.
Forehead kiss, kiss on the cheek or a real one: which do you like getting from me most?
Why ask it
A sweeter question than it looks, since a guy who loves the forehead kiss can feel silly saying so. Whatever he picks, that's the one to give him when you next leave the room. Ask which he thinks you like best and see if he's right.
What would you do if I kissed you right now, halfway through your sentence?
Why ask it
Asked in person, it is a warning and a dare at once. Over text it becomes a promise for later. If he claims he would carry on talking, you're allowed to check.
Big spoon or little spoon, and would you admit your answer to your friends?
Why ask it
The second half is where the teasing is. A guy who owns up to little spoon without flinching is secure, and one who protests too much has answered anyway. Good for the sofa halfway through a movie.
When we're out with other people, do you ever wish it was just the two of us?
Why ask it
Whisper it at the party instead of saving it for the ride home. 'Since about an hour ago' means you can agree on a leaving time together. If he's having a great night with his friends, a happy 'not yet' is fine, and you've still told him where your head is.
Do you like it more when I reach for your hand first, or when you get there before me?
Why ask it
Small enough to ask in the middle of a walk, with your hand already halfway to his. 'When you do' usually means he likes being picked where people can see, and doing it more costs you nothing. If he has never thought about it, take his hand and ask again in a minute.
Is there something flirty I used to do that you'd like me to do more?
Why ask it
The answer is usually modest: texting first, sitting on his side of the booth, saving him the last bite. If he suggests something you're not up for, say 'not that one, pick again' and keep the tone light; you decide how far any of this goes. Then ask what he'd bring back in return.
What's the most romantic thing you've thought about doing for me and haven't done yet?
Why ask it
He admits to the idea without having to deliver it tonight, so shy planners can answer. Don't ask why he hasn't; say you'd love it and leave it there. A long pause followed by 'I can't tell you' is the best possible sign.
So, are you going to kiss me, or do I have to keep asking questions?
Why ask it
Save it for when his answers have been good and you're done talking. It needs a grin and about one second of eye contact. Not one for text, unless he's already on his way over.
How to flirt with someone you're already dating
Practical guidance for the conversation itself
Before you ask
Flirting with a boyfriend is a different job
With a guy you've just met, a flirty question finds out whether he's interested. With a boyfriend you already know, so the question is there to remind you both. That takes the pressure off: no reply can go badly wrong, and you can afford to be sillier.
Pick three, not the whole page
Read through, choose a few that sound like you, and change the wording until they do. A line that isn't in your voice gets 'where did that come from', which is funny once and tiresome five times.
Choose a moment he can answer in
Teasing lands when he's relaxed: on the couch, on a walk, in the car. It falls flat when he's mid-game, late for something or worn out from the day. If a question gets a grunt, suspect the timing before you suspect the question.
Follow the groups in order
Teasing and Compliments are the warm-up and suit any day. How we started and Date nights need a little time, so keep them for an evening. Over text is its own group for the hours you're apart. A little bolder goes last, once you've both been laughing for a while.
On a night in
One question, then a conversation
Ask one, and stay with whatever he says until it runs out on its own. If the first-kiss question turns into twenty minutes of arguing over who was more nervous, the list has done its work and you can put it away.
Answer everything you ask
Have your own answer ready and give it whether or not he asks. Half the flirting is in what you tell him: when you first wanted to kiss him, what he does that distracts you. When only he answers, it starts to feel like a quiz.
Let him be bad at it
A boyfriend who is out of practice at flirting will answer a playful question literally. Laugh, give him an example of the answer you were fishing for, and ask the next one. He usually catches on within a few.
Turn answers into plans
The Date nights group is only worth asking if something comes of it. When he names a place, a meal or a Saturday, put it in the calendar that night. A plan that actually happens is what makes him answer properly next time.
Over text
One a day at most
A single flirty message in an ordinary day stands out. Six in a row read like a list you found online, and he'll answer only the last one.
Send it when he can smile at it
Lunch, the end of a commute and the evening are good. The middle of a meeting or an exam is not. A late reply to a flirty text means a busy afternoon, so don't follow it with a second message asking whether he saw the first.
Make the joke visible
On a screen, 'am I more trouble than you expected' can sound like a real worry. Add the emoji you'd normally use, or a second line that gives the game away, so he knows which answer you're after.
Keep photos to faces
The texts here ask for nothing more than a selfie, and that's on purpose. Anything you send can be saved, so send only what you'd be fine with existing forever, and treat his pictures as carefully as you'd want yours treated.
Finish it in person
The best use of a flirty text is to set up the next time you see him. If he says what he'll do when he sees you, or names the date he'd repeat, bring it up at the door. A thread that never leaves the phone goes stale.
Reading his answers
What playing along looks like
He teases back, asks you the same question, or brings it up again an hour later. A guy who says 'wait, ask me another one' is having a good time, however gruff the answers.
A flat answer
'I don't know' or 'you're fine' can just be tiredness or shyness, not a verdict on you. Drop it for the night and try a different group another day. If playful questions get nothing week after week and that bothers you, tell him so plainly outside the game; a flirty question is the wrong tool for that conversation.
When he takes it further than you want
Some answers will push toward more than you meant. 'Not tonight, pick again' said with a smile is enough, and a good boyfriend takes it without sulking. You set how far the flirting goes, every time, and so does he.
When a question turns serious
Asking about the first kiss or the first month sometimes brings up something real: a doubt he had, a time he nearly didn't call. Let it be serious for a minute and listen. You can go back to teasing afterward, and it's usually better for the detour.