Cute Questions to Ask Your Boyfriend
For anyone with a boyfriend and an evening to fill, on the couch, on a long call or in the last text of the day, who wants him smiling and a little embarrassed and not a serious talk. The 91 questions run in six groups, in the order you'd likely use them: Early days, Little things, Our memories, Would you rather, Daydreams, and By text for the ones that fit in a single message. The notes say what to say back, and a good many show how one question can turn into a small tradition between the two of you.
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The questions
Each question, and why to ask it
Early days
What was your very first impression of me, before we'd said a word to each other?
Why ask it
He may remember a laugh from across the room, a jacket, or that you looked busy. Give him your first impression of him right after, down to what he was wearing or holding.
What was I doing the moment you realized you had a crush on me?
Why ask it
It tends to be something you'd never have guessed, like the way you argued about a movie or held a door open with your foot. Once you know what it was, you won't do it again without catching his eye.
What did you do to get my attention back then, hoping I'd notice?
Why ask it
Expect a confession: laughing too hard at your jokes, taking the long way past your desk, learning a band he'd never heard of. Tell him which move really worked, since it's rarely the one he planned.
Who did you tell about me first, and what were your exact words?
Why ask it
A best friend, a brother and his mom each mean something a little different. Have him repeat the words the way he said them then, and you get a small performance of him being smitten.
Were you nervous the first time you held my hand, and could I tell?
Why ask it
A yes is the answer you're hoping for, so no teasing when you get it. Take his hand while he's answering and ask whether it's any easier now.
What do you remember about our first kiss that I probably don't?
Why ask it
The details you missed are probably his to supply: how long he'd been working up to it, what was on the radio, the dog barking next door. If his telling and yours don't match, leave it unsettled. Two accounts of one kiss are better to own than one.
How long did it take you to work up the nerve to text me first, and what did you nearly send?
Why ask it
If you were the one who texted first, flip it and ask how long he stared at your message before replying. The drafts nobody sent are the best part, so offer one of your own.
What did you wear on our first date, and how long did it take you to pick?
Why ask it
Guys who claim they threw on the first clean shirt have sometimes tried three. Whatever he admits to, describe what you remember him wearing and see how close you get.
What's something I said early on that you can still repeat word for word?
Why ask it
You will probably not remember saying it, and that's fine. Don't correct his version; a line he has carried around this long belongs to him now.
What were you sure about me in the first week that I've since proved wrong?
Why ask it
Most of these are flattering by accident: he thought you'd be hard to talk to, or wouldn't like his kind of music. Trade one back, and keep yours to the harmless kind.
What was our very first inside joke, and do you remember how it started?
Why ask it
If neither of you can trace it, that's an answer too, because it means there have been a lot of them since. Bring the old one back for a day and see how long he takes to catch it.
Be honest: how far back did you scroll through my photos when we first started talking?
Why ask it
Everybody scrolls and hardly anybody owns up to it, so reward honesty with honesty and admit how far you went. Then ask which old photo he nearly liked by accident.
What was the first song, show or snack you got into only because of me?
Why ask it
Whatever it is, it's part of his week now and it arrived with you. Name the thing you picked up from him, then swap one new recommendation each: that trade can run once a month for as long as you like.
What's the first gift you ever gave me, and how long did you agonize over it?
Why ask it
The agonizing is the sweet part: three stores, a sister consulted, a receipt kept just in case. If you still have the gift, go and get it while he's talking.
Little things
What's the cutest thing I do without realizing I'm doing it?
Why ask it
The answer is usually a habit you'd have stopped if you knew about it, like humming while you cook, so take it as a compliment and carry on. He has one too, and now is the time to say what it is.
What's your favorite thing about the two of us as a couple?
Why ask it
This one is about the pair of you, and he may reach for something like 'we can be quiet together' or 'we're never bored in a line.' Whatever he names is worth protecting on purpose, so point it out the next time it happens.
What's your favorite thing about me that most people would never notice?
Why ask it
You're asking for the detail only someone close would see: that you remember everyone's order, or always wave the other car through first. Name one of his next, and be just as specific.
Which of my faces do you like best: the sleepy one, the concentrating one or the trying-not-to-laugh one?
Why ask it
He may add a fourth you didn't know you had. Ask for his impression of it, and accept that it will be unflattering and accurate.
What do I say so often that you can hear it in my voice when I'm not around?
Why ask it
A catchphrase you didn't know was a catchphrase. Once it's been named you'll both hear it every time, and it tends to become a joke the two of you keep for good.
What's the surest way to get my real laugh, the one I can't hold in?
Why ask it
If he knows the trigger he's been paying attention, and he'll probably try it on the spot. Let him in on what does the same to him, in case he hasn't worked out that you do it on purpose.
What's your favorite way I say hello after we've been apart all day?
Why ask it
Maybe it's a running hug, a text from the driveway or just how you say his name. Whatever he names, make it the standard greeting for a week and watch whether he notices.
What small thing do I do for you that improves your whole day?
Why ask it
Small is the rule: saving him the last bite, sending a photo of a dog you passed. Now you know what to keep doing, and it costs you almost nothing.
When I'm away for a few days, what's the first thing about me you notice is missing?
Why ask it
Hope for something small and odd, like your running commentary during a show or the way you take over his playlist. That is the thing to send him a little of while you're away: a voice message, a photo, one line of commentary.
Which of my outfits is your favorite, and what do you remember about a day I wore it?
Why ask it
Expect a bad description, 'the green one with the things on the sleeves,' sincerely meant. Wear it the next time you see him and don't mention this conversation.
If you had to sum me up in one word, what's the word, and what was the runner-up?
Why ask it
One word is hard, so give him a minute and don't supply options. The runner-up is often the more honest of the two. Write both down with the date, because this is a good one to ask again in a year.
What habit of mine would you miss if I ever stopped?
Why ask it
This turns a quirk you may be self-conscious about, like stealing his fries or sending eleven texts in a row, into something he's fond of. Believe him, and send the eleven texts.
How can you tell I need a hug before I've said a word?
Why ask it
If he can list the signs, the quiet, the sleeves pulled down over your hands, he has been reading you for a while. If he can't, tell him what they are. It saves you both a guessing game on the next rough day.
When do I look happiest to you: what am I doing, and who's around?
Why ask it
His answer shows you yourself from across the room: singing in the car, halfway through a plate of something, talking about one particular friend. It's also a short list of what to do on a day that needs rescuing.
What smell makes you think of me right away: a shampoo, a food, a place?
Why ask it
It might be your shampoo, or it might be the fries from wherever the two of you always end up. If it's something you can lend, like a hoodie or a scarf, leave it with him the next time you'll be apart for a while.
If the two of us had a song, which one is it, and where were we when it became ours?
Why ask it
It doesn't need to be a love song; a track from one long drive counts. If you can't agree, each of you nominates one and you play both, and the one that gets turned up wins.
What's your favorite nickname for me, and where did it come from?
Why ask it
The origin story is the point, particularly when the name began as a mistake or a joke. If he says he doesn't have one, he has just volunteered to come up with one by the weekend.
What's something silly we do together that you'd never admit to your friends?
Why ask it
The voices you give the cat, the song you both sing while the microwave counts down. Promise the secret is safe, and then do the silly thing right away.
What do you like about being in the same room with me while we each do our own thing?
Why ask it
One for the quiet kind of boyfriend, who often likes this best and has never said so. If he lights up, plan an evening of exactly that: his game, your book, one couch.
Our memories
What's your favorite memory of us from this past year?
Why ask it
Limiting it to one year makes it answerable, where 'favorite memory ever' leaves a lot of people blank. Ask it again every December or on your anniversary, and keep the answers together in one place.
What small moment with me do you replay when you're having a bad day?
Why ask it
Keep it light by asking only for the scene: where you were and what the two of you were doing. Which moment he reaches for tells you what kind of time with you matters most to him.
When did we last laugh so hard that one of us couldn't breathe, and what set it off?
Why ask it
Retelling it usually starts you both up again, and it won't be funny to anyone else, which is as it should be. If you can't agree on who started it, argue the point; that tends to be round two.
What's the best date we've been on so far, and at what point did it become the best?
Why ask it
The turning point is the useful half: when the rain started, when the band turned out to be terrible, when you both gave up on the plan. It shows you what he counts as a good time, which is seldom the expensive part.
What's your favorite memory of us that nobody else was there to see?
Why ask it
With no witnesses, only the two of you can keep it alive, so fill in whatever he leaves out. A good one for a long call when you're missing each other.
What's the best rainy day we've ever spent together?
Why ask it
Rainy days are when plans fall through and something better happens by accident. File his answer away for the next wet weekend and suggest it as though you'd just thought of it.
What's the best car ride we've ever had, and where were we headed?
Why ask it
A drive makes for easy talking, with nobody having to make eye contact. Ask who was driving and who was in charge of the music; if he remembers a song from it, that's the first track of a playlist you both add to after every good drive.
What's the sweetest thing I've ever done for you, by your count and not mine?
Why ask it
Your guess and his answer will often be different things: you'd say the birthday you planned, and he says the night you showed up with soup. His pick tells you which kind of gesture reaches him, big or small, planned or not.
What's the funniest thing that's ever gone wrong on one of our dates?
Why ask it
A closed restaurant or a flat tire makes a better story than any evening that went to plan. Tell it together, taking turns, and notice whose version gets more dramatic.
What of mine have you ended up with that you have no plans to give back?
Why ask it
A hoodie, a book, a pen from your bag, a phone charger. Let him keep it, and name the thing of his that has quietly become yours, so the exchange is official on both sides.
Which picture of the two of us makes you smile every time you scroll past it?
Why ask it
It's often a blurry one where neither of you was ready. Get it printed: a photo on paper, stuck to a mirror or a fridge door, gets looked at far more than one buried in a camera roll.
When did you look over at me and think, I'm lucky?
Why ask it
He may go shy here, so give him a second and don't fill the silence. When he's answered, tell him yours instead of just saying 'aw'; it's a lot to say out loud and get nothing back.
What's your favorite thing we've ever cooked or baked together, disasters included?
Why ask it
The burnt and collapsed ones count double. Pick a date to attempt it again, and agree in advance that whoever ruined it last time is on dishes.
Which memory of us sounds boring when you tell it and is one of your favorites anyway?
Why ask it
Waiting for a train, folding laundry, a walk to nowhere. An answer like that is about the kindest thing he can say, because it means the company was the event.
Would you rather
Would you rather have a dressed-up dinner out with me or pizza on the floor in our pajamas?
Why ask it
Plenty of boyfriends pick the floor, which is good news for everybody's budget. Whichever he chooses, make it the plan for your next free night and let him pick the toppings or the restaurant.
Would you rather find a note from me in your jacket pocket or open the door to a surprise visit?
Why ask it
A note can be kept and a visit can't, so the answer says whether he's a keeper of things or a moments person. Either is easy to arrange, and he won't see it coming if you wait a few days.
Would you rather share one pair of earbuds with me on a long bus ride or one umbrella in the rain?
Why ask it
Both are excuses to stand closer than strictly necessary, which is the whole idea. If he says earbuds, ask what he'd put on; if he says umbrella, ask who ends up holding it and who ends up wet.
Would you rather have met me a year sooner or get one extra hour with me every day from now on?
Why ask it
A year sooner means he thinks you'd have been good for him back then, so ask what he was up to that year. The extra hour means he'd like more of now, so ask which hour of the day he'd put it in.
Would you rather I sang to you badly in public or wrote you a terrible poem and read it aloud at home?
Why ask it
Both are a threat and he knows it. Honor his pick on the spot with four lines or one chorus, and make it clear he owes you the other option.
Would you rather spend a whole Saturday doing my favorite thing or have me spend one doing yours?
Why ask it
Either choice is generous, just in different directions. Do both on back-to-back weekends, with a rule against sighing.
Would you rather I texted you a running commentary on my day or saved it all up for one long call at night?
Why ask it
A practical question dressed as a game, since you can simply start doing what he picks. Say which you'd like from him, too. When one of you narrates everything as it happens and the other goes quiet until evening, it helps to know that neither is a mood.
Would you rather take me on a picnic or to a fair where you have to win me a prize?
Why ask it
The fair is the bolder pick, because the ring toss has humbled better men. If he chooses the picnic, each of you packs one thing the other doesn't know about.
Would you rather the two of us had a secret handshake or a secret code word for 'let's go home'?
Why ask it
The code word is the useful one at a party that has gone on too long, and the handshake is the one you'll still be doing in ten years. Invent whichever he picks before the evening is over, and practice it once.
Would you rather have matching hoodies or matching phone wallpapers?
Why ask it
One is seen by the whole street and the other only by the two of you, so it's a gentle read on how public he likes his affection. If he picks neither, negotiate down to matching socks.
Would you rather get lost with me in a city neither of us knows or show me around the town you grew up in?
Why ask it
One is an adventure and the other is an introduction to who he was at twelve. If he picks his hometown, ask for the first three stops on the tour, and expect one of them to be a place that sells food.
Would you rather dance with me in the kitchen where nobody can see or at a wedding where everybody can?
Why ask it
If he says kitchen, put on a song and collect right then. If he says wedding, he's braver than he lets on, and you can hold him to it at the next one.
Would you rather I always knew what you were thinking or always knew which snack you wanted?
Why ask it
The snack is the wise choice and he'll probably see that. Use the follow-up to learn his snack for a good day and his snack for a bad one.
Would you rather fall asleep halfway through a movie with me or stay up talking until it's far too late?
Why ask it
Nobody's wrong here: one answer says he's comfortable enough to nod off next to you, and the other says he'd trade sleep for the conversation. If he picks the movie, he's also agreeing that you get to choose it.
At the end of a call, would you rather be the one who hangs up or go three more rounds of 'no, you hang up'?
Why ask it
A sweet one for late calls, and a way to find out whether the long goodbye charms him or wears him out. If he likes the three rounds, keep them; if he doesn't, agree on a sign-off line and count down to it together.
Daydreams
What's one small thing you'd like us to do every week, just the two of us?
Why ask it
Hold him to something small enough to survive a busy week: a Thursday walk, pancakes on Sunday, one episode saved for each other. Start it this week, before either of you forgets it was said.
What would our perfect date be if we had a whole free day and only forty dollars?
Why ask it
A budget forces invention and keeps the answer doable. Plan your own version separately, compare the two, and merge the best halves into a real day.
If we got a pet together someday, what would it be and what would we call it?
Why ask it
The naming debate is the real game. Each of you gets three names and one veto, and the winning name goes to a plant or a stuffed animal in the meantime.
What would breakfast look like in a place that was ours: who's cooking and who's still asleep?
Why ask it
Treat it as a daydream and not a plan, so nobody feels a timeline arriving. The casting is the fun: he may hand himself the coffee and you the pancakes, and you're allowed to object.
Where's one place you'd love to watch a sunset with me?
Why ask it
A far-off beach is a fine answer, so follow it with the nearest place that would do for now. A hill or the top of a parking deck ten minutes away counts, and you could be standing on it by Friday.
What's something you've never done that you'd like to try for the first time with me?
Why ask it
Steer it small if he goes straight to skydiving: a food he's never eaten, ice skating, a sport he has only watched. Firsts make a date easy to remember, so write his answer down.
What show, movie series or game do you want us to get through together from start to finish?
Why ask it
Agree on the one rule that matters, which is no going ahead alone. A shared series is something to look forward to on dull weeknights and a reason to call when you're apart.
Which holiday are you most excited to spend with me this year, and what's the one thing we have to do?
Why ask it
The one thing is what matters: carving a pumpkin badly, a certain movie, driving around to look at lights. Do it this year and again the next, and it's a tradition.
If we planned a tiny trip an hour from here, where would we go?
Why ask it
An hour away is close enough to happen. Have him name the place and one thing to eat there, then look at a calendar together before the idea cools.
What do you want our next photo together to be of?
Why ask it
A way to hear what he'd like to do next without asking him for a plan: at a game, on a hike, covered in flour. Then go and take that photo.
What from when you were a kid do you most want to show me: a place, a movie or a snack?
Why ask it
He's offering you a piece of himself at nine, so go in willing to like it, even when the movie has aged badly. Your favorite from that age goes on the list as well, and gets the same fair hearing.
If one table somewhere was always held for the two of us, where would you want it to be?
Why ask it
He'll likely name a place you already go, and seldom the nicest one. Sit at the same table there twice and it's yours as far as the two of you are concerned, no reservation required.
If we kept a list on the fridge of things to do together, what would you write first?
Why ask it
Make the list real, on paper or in a shared note, with each of you adding one thing a month and crossing one off. His first entry is the thing he's been quietly wanting to do.
When we're old, what's one silly thing you hope we still do?
Why ask it
It's a daydream about staying playful, so racing to the car or splitting one dessert is right on target. Add yours, and neither of you is allowed to be sensible.
By text
What's one thing that made you smile today? I want to hear it before I fall asleep.
Why ask it
A goodnight text that asks for something small and good. Send yours back in a line; done most nights, it turns into the way the two of you end the day.
What were you doing today when I popped into your head?
Why ask it
The honest answers are unglamorous, like waiting for the microwave or passing a dog that looks like yours, and those are the ones to hope for. It beats asking whether he thought about you, which has only one polite answer.
Send me the emoji that looks most like me. Why that one?
Why ask it
He will pick something ridiculous first, so demand a serious second attempt. Put the winner next to your name in his contacts, and send back the one that's him.
Text or voice message: which would you like from me at the end of a long day?
Why ask it
Some people want to hear a voice and some want words they can read twice, and it's hard to guess which from outside. Whichever he says, send one tonight so he knows you meant it.
What should I dream about tonight?
Why ask it
He gets to be silly or sweet in a single line, and you report back in the morning on what you really dreamed. That report carries the thread into the next day.
Good morning. What's the first thing you thought when you woke up?
Why ask it
It will usually be 'five more minutes' or breakfast, and that's fine: you're asking to be let into his morning, not to be the answer. Send your own first thought, however unromantic.
How much do you miss me right now, from 'a normal amount' to 'it's getting embarrassing'?
Why ask it
The joke scale lets him say it without feeling sappy. Answer one notch higher than whatever he says.
Tell me one nice thing about me that I can read again tomorrow morning.
Why ask it
Asking outright feels bold, but plenty of people are glad to be told what's wanted. Screenshot it, and send him one unasked the next day so it doesn't only go one way.
What's on your lock screen right now, and do I need to send you a better photo?
Why ask it
If it's his dog or a team logo, you've lost to worthy competition. Send three options anyway and let him choose.
What would our chat be called if we had to give it a name?
Why ask it
A two-person chat with a title is a tiny shared joke you both see many times a day. Take turns renaming it whenever something funny happens.
Fill in the blank: you're my favorite person to ___ with.
Why ask it
Send your own completed version first so he has a pattern to copy. 'Do nothing' and 'get lost' are both excellent answers, and you can play again whenever the thread goes quiet.
Pick one for this weekend, no thinking: sunset walk, movie night or breakfast date?
Why ask it
This one ends in a plan. Whatever he picks, reply with a time, so it's on the calendar while he's still looking at his phone.
What song should I play on the way home so I think of you?
Why ask it
Listen to it for real and text him one line about it when it finishes. Asked every Friday, it becomes a small weekly handover: his song for your ride home, and yours for his.
Something I just saw reminded me of you. Three guesses what it was?
Why ask it
Have the photo ready before you send this. A hint after each miss keeps it going, and what he guesses, a dog, a snack, a terrible car, is a look at how he thinks you see him.
Sweet dreams. What's one good thing waiting for you tomorrow?
Why ask it
It sends him to sleep thinking about something he's looking forward to. If he can't find one, give him one: a call at lunch, a coffee you'll bring, a plan for the evening.
Sweet questions, and the small traditions they start
Practical guidance for the conversation itself
Which group for what you're after
When you want a story
Early days and Our memories are storytelling questions, and a story wants time and a face to tell it to. Ask them in the same room with nothing else on, and expect to get through two or three, not ten. If the story of the first text takes up the whole evening, the evening went well.
When you want to hear something nice
Little things is the group that gets you compliments, so ration it. One of these in an evening is a pleasure for both of you; five in a row and he's being asked to perform. Give one back each time, as specific as the one you got, and tuck these in among the memories and the would-you-rathers, where they come as a surprise.
When you want something to do
Would you rather and Daydreams nearly all end in a thing the two of you could do: the picnic, the code word, the town an hour away. They need no props and nothing looked up, so they carry a long call when neither of you has any news. Keep a note open on your phone, because the answers are plans.
When you have one line
The By text group is written to be answered in a line. Send one question at a time, at an hour when he's winding down and not in the middle of a shift or a game. One that arrives at about the same time most nights becomes something he waits for, and before long he'll be the one who sends it first.
Small traditions that start with one question
The Sunday question
Pick one evening a week and ask a single question from Little things or Our memories, over dinner or on the phone. Take turns choosing it. At one a week those two groups last more than half a year, and the habit never feels like homework.
The shared note
Keep one note on both your phones and add the best answer each time, with the date. It takes a minute, and in a year you'll have a page of small things he said about you that you would otherwise have forgotten. He can add yours.
The same five every year
Choose five questions, such as the one-word summary, the song that's yours and his favorite memory of the past year, and ask the same five on every anniversary or New Year's Eve. Compare them with last year's. Which answers change and which stay put is the entertaining part.
The jar
Write twenty of the questions on slips of paper, fold them and keep them in a jar or a mug near where you both sit. Either of you may pull one on a flat evening. Put in a few blank slips so he can write his own for you.
When the answer isn't what you pictured
He can't remember
If he has no idea what he wore on your first date, or which of you texted first, that is a funny fact about him and not a verdict on the two of you. Tell him what you remember and let him be amazed by it. These questions only work when drawing a blank is a safe answer.
He says 'I don't know'
Some people freeze when asked for a feeling on the spot, and it doesn't mean there isn't one. Offer two options. 'What's the cutest thing I do?' can get a shrug where 'Is it the humming or the thing with the socks?' gets an answer, and often a third option you hadn't thought of.
He turns it into a joke
A boyfriend who answers 'What's the first thing you notice is missing?' with 'your snacks' has still answered, and may be telling the truth. Laugh first. If you'd like the other answer as well, ask for the real one too, once and lightly, and take what you get.
It lands heavier than you meant
Now and then the daydream about breakfast in a place of your own sounds like a timeline to him, or the moment he replays on a bad day arrives with the bad day attached. Follow where he goes if he wants to talk, and let it drop if he doesn't. The light questions will keep.
You wanted it to settle something
If you catch yourself asking these to find out whether things are all right between you, stop and ask that instead, plainly, on another evening. A sweet question asked as a test stops being sweet, and he'll feel the difference. The same goes for the middle of a disagreement: this list is for the good evenings.