Fun Questions to Ask Your Boyfriend
For a car ride, a slow evening or a text thread with your boyfriend, when you want to laugh and not to have a talk. The 98 questions run in six groups: Funny hypotheticals, Random favorites and small debates, Would you rather, Know me (a quiz on how well he knows you), Cute, and Over text for the ones that fit in a single message. Every question has a note with the follow-up to ask or the game to make of it.
Want questions from the whole vault instead? Try the random question generator.
The questions
Each question, and why to ask it
Funny
Would you still love me if I turned into a worm?
Why ask it
A famous one, and the only wrong answer is a long pause. Move on to the practical side: what he'd keep you in, and whether a worm still gets a vote on what's for dinner.
What animal do you think you are, and what animal do you honestly think I am?
Why ask it
He'll likely pick something noble for himself and something small and loud for you. Make him give evidence for both, then tell him which animal he really is.
If the two of us started a band, what's it called and who plays what?
Why ask it
Neither of you being able to play anything is not a problem, it's the premise. Push for the title of the first album, and for which of you storms out of the band first.
Which of your friends would you trust to plan a heist, and which one would get everybody caught?
Why ask it
He'll cast his whole friend group in under a minute, and you'll hear who he thinks is sharp and who he just loves. Then ask what job you'd get on the crew.
If somebody left the two of us a one-star review as a couple, what would it complain about?
Why ask it
It lets him tease the pair of you as a unit: too many inside jokes, forty minutes to choose a movie. Write the five-star review next, and see whether it brags about the same thing.
If you could only eat from one aisle of the grocery store for a week, which aisle are you living in?
Why ask it
Don't let him stop at 'snacks': he has to name a breakfast, a lunch and a dinner from that aisle. Then make it a dare, with each of you planning one real dinner from your aisle on the next shopping trip.
If you could keep any animal as a pet with zero consequences, which one is moving in?
Why ask it
A capybara person and a tiger person want different things out of life. Make him say where it sleeps and who walks it, because the details are where he starts laughing.
If you were arrested for something completely harmless, what would your friends assume you'd done?
Why ask it
The answer is his own read on his reputation: feeding ducks where it's banned, arguing with a referee at a kids' game. Follow up by asking whether you'd be his one phone call or the person he'd hide it from.
What's the dumbest thing you'd buy with lottery money before doing anything sensible?
Why ask it
Everyone's sensible list is the same, so skip it. Give each of you one ridiculous purchase with no budget and compare: an arcade machine and a hot tub can share a house.
If a theme park were built about your life, which ride would have the longest line?
Why ask it
The long line is the story he's proudest of, and he'll tell it. Ask which ride nobody would get on, and what the gift shop sells.
Which store or restaurant would it hurt most to be banned from for life?
Why ask it
You find out where his money and his Saturdays really go. The better follow-up is what he'd have to do to earn the ban.
If you were the villain in a kids' movie, what would your very mild evil plan be?
Why ask it
Mild evil plans are pet peeves in a cape: banning slow walkers, abolishing Monday mornings. Whatever he'd outlaw is the thing to tease him about the next time it happens in real life.
Which celebrity gets cast as you in the movie about us, and who do they get to play me?
Why ask it
He'll cast himself generously, so watch what he does with your part. Swap answers, then choose the scene from your real life that would have to make the final cut.
If you had to compete at the Olympics next month, which event gets you the least embarrassing result?
Why ask it
The reasoning is the entertainment, usually some version of 'all I'd have to do is not fall over.' Finish by picking the event the two of you would enter as a pair.
What's the most useless superpower you'd still be thrilled to have?
Why ask it
Set the bar with one of your own, like never stubbing a toe or always finding a parking spot on the first pass. Score them together: the winner is the power that's most pointless and would still get used every day.
If you were famous, what would the paparazzi keep catching you doing?
Why ask it
It's how he sees his own most ridiculous public habit, whether that's buying four of the same snack or losing an argument with a self-checkout. Confirm it, or add the one he left out.
If you had to live inside one movie or show for a month, which one, and how soon would you want out?
Why ask it
Most dream worlds turn out to have terrible plumbing, so the second half gets the laugh. Check whether you're invited, and take a no in good spirit if the place is full of dragons.
Random
What's a meal that only one person on earth makes the right way, as far as you're concerned?
Why ask it
Find out what makes theirs different, and whether you're allowed to attempt it or should leave it well alone. If the cook is a grandparent, the dish tends to arrive with a story.
What food does everybody seem to love that you just don't get?
Why ask it
Find the one where the two of you disagree and make him try a bite of a good version. Fair is fair, so he gets to pick one for you.
What was your favorite thing you owned as a kid, and what happened to it?
Why ask it
The fate is the story: left on a beach, sold at a yard sale, still in a box in his parents' garage. If it survived, ask to see it.
What's the first concert or big game you remember going to, and who took you?
Why ask it
Who took him is the better half of the answer. It often brings in an uncle, an older sibling or a friend's dad you've barely heard about.
What's the last thing you looked up at two in the morning?
Why ask it
Late-night searches are pure curiosity: how tall an actor is, whether sharks sleep. Trade yours, with the rule that nobody has to explain.
What smell takes you straight back to being a kid?
Why ask it
Smell answers come with a place attached, so ask where he's standing when it hits him: a grandparent's kitchen, a pool deck, the back seat of a certain car.
What did you believe as a kid until an embarrassingly late age?
Why ask it
Most of these are oddly logical, which is what makes them funny. Find out who finally set him straight and how he took the news.
What's a pointless fact you can't seem to forget, and who or what taught it to you?
Why ask it
The source is the better half: a cereal box, a substitute teacher, one documentary watched at the wrong age. Trade one each, and whoever can't back theirs up with a quick search owes the other a snack.
What's your favorite day of the year that isn't a holiday or your birthday?
Why ask it
Opening day, the first warm evening and the Friday before a long weekend all count. Remember his, since it's a day you can quietly plan something small around.
What did you want to be at seven, and what would you pick now if money and talent weren't an issue?
Why ask it
Put the two answers side by side. Sometimes the astronaut has turned into a man who wants a quiet bike shop, and how he got from one to the other is a good ten minutes.
Pineapple on pizza, ketchup on eggs, cereal for dinner: which one are you defending?
Why ask it
One question, three possible arguments. Take the opposite side for five minutes even if you agree with him; a fake fight over toppings is more fun than nodding.
What's the most overrated thing that people our age pretend to enjoy?
Why ask it
A harmless grumble about brunch lines or a show everyone quotes tells you what he's only doing to be polite. Worth knowing before you plan a weekend around it.
What's the right way to spend a day off: a full plan or no plan at all?
Why ask it
You probably know which side he's on, but hearing him argue it is the point. The loser of the debate does the next free Saturday the winner's way without complaining.
What song do you know every word of and have no idea why?
Why ask it
Insist on a few bars, since this one is wasted if he only names it. The usual culprits are a commercial jingle, a cartoon theme or something a sibling played all summer.
What's the oddest compliment anyone has given you that you still think about?
Why ask it
Get the name of whoever said it and how long ago, because the odd ones get carried around for years. Then give him one of your own that's just as strange and just as true.
What small treat stays in your budget no matter how tight money gets?
Why ask it
Make a quiet note of the answer, whether it's good coffee, one brand of socks or the streaming service with his sport on it. You've just been handed a gift idea that can't miss.
Would you rather
Would you rather skip every line you ever have to wait in or never see another ad for the rest of your life?
Why ask it
A patience test in disguise. If he picks lines, ask which line he hates most, and you'll know where not to take him on a Saturday.
Would you rather I planned your whole birthday as a surprise or you picked everything and I just showed up?
Why ask it
The one would-you-rather here with a practical use. Remember what he says and act on it, because once a surprise is underway it's too late for him to tell you he'd have liked a say.
Would you rather sit next to a nonstop talker on a long flight or in front of a kid who kicks the seat?
Why ask it
Have him say what he'd do about it, too. Whether he'd put up with it in silence or turn around politely is a fair preview of traveling with him.
Would you rather eat only breakfast food forever or never have breakfast food again?
Why ask it
Pancake people answer before you finish the sentence. If you land on opposite sides, the compromise is breakfast for dinner this week, his choice of menu.
Would you rather be unbeatable at every video game or pretty good at every sport?
Why ask it
The choice is between crushing one room and being welcome in every pickup game. See which friend he'd most want to beat first.
Would you rather be stranded on an island with me and no snacks or alone with a full pantry?
Why ask it
Nobody should pass this loyalty test too quickly, and a long think is the honest answer. Ask which three snacks would have tipped it, then answer it yourself without flinching.
Would you rather never wash another dish or never sit in traffic again?
Why ask it
Both are daily, both are dull, and people feel surprisingly strongly. His pick is the one he'd be most grateful to have taken off his hands once in a while.
Would you rather get matching tattoos chosen by my mom or matching haircuts chosen by yours?
Why ask it
Make him describe what each mother would pick before he decides, because the descriptions are the game. Swap in a sibling or a best friend if a mom isn't an easy subject for either of you.
Would you rather know the ending of every movie before it starts or never be able to watch the same movie twice?
Why ask it
This sorts the rewatchers from the people who hate spoilers. If he'd give up rewatching, find out which one film he'd beg an exception for.
Would you rather lose your phone for a week or lose your voice for a week?
Why ask it
Play it out: how does he order food, tell a joke or win an argument? If he keeps the phone, propose a silent hour where you can only text each other from the same couch.
Would you rather have a dog that talks but is rude to guests or a cat that cooks but judges everything you eat?
Why ask it
No sensible answer exists, which is the charm. Get him to do the voice, and to say what the pet would report about the two of you.
Would you rather I picked your outfits for a week or your lunches for a week?
Why ask it
It comes down to which he trusts more, your taste or your idea of a decent meal. Offer to make it a real trade for three days, and let him pick yours.
Would you rather narrate your own life out loud for a day or have me narrate it?
Why ask it
Try thirty seconds of each right now. Narrating him making a sandwich in a nature documentary voice is usually enough to settle it.
Would you rather be famous for something embarrassing or unknown for something great?
Why ask it
He'll have the embarrassing thing ready before you ask, so ask. Save this one for a long drive, because the answers wander.
Would you rather travel back to meet me as a kid or forward to see the two of us at eighty?
Why ask it
The sweet one of the group. If he picks the past, tell him what he'd have found; if he picks the future, ask what he hopes the two of you are bickering about.
Would you rather drive all ten hours of a road trip or navigate the whole way with a paper map?
Why ask it
Best asked on the road itself. You'll find out who wants the wheel and who wants the snacks, and that can be settled before the next long trip.
Know me
What's my usual order at a coffee shop, word for word?
Why ask it
Write it down before he answers so nobody can dispute the result. Half credit for the right drink in the wrong size, and he gets to quiz you on his.
Which food will I pick off my plate every single time?
Why ask it
He's probably the one who ends up eating it, so he ought to know. A right answer makes the olives or the pickles officially his from now on.
If I've gone quiet in another room for an hour, what am I most likely doing?
Why ask it
His guess is a little portrait of how you look from outside: reorganizing a drawer, deep in a video about a stranger's kitchen. Tell him how close he was, then guess his.
Which song do I always skip, and which one must never be interrupted?
Why ask it
Two answers, two points. Test it on the next drive by handing him the playlist and watching what he does with it.
What's my middle name, and for a bonus point, my shoe size?
Why ask it
Plain facts are where confident people come undone. Keep it kind if he misses the shoe size, which is a thing nobody is ever told outright.
What's my biggest pet peeve, and when did you last set it off?
Why ask it
A boyfriend who names it instantly has been tiptoeing around it for months. If he's wrong, he's about to learn what it is, so tell him nicely.
What three things are always in my bag or my pockets?
Why ask it
Three is hard enough to be a real test. For extra credit, have him name the one you'd panic over losing, then empty the bag and check.
Which emoji do I use the most, and which one do I use wrong?
Why ask it
He can't check his phone until he's locked in an answer. The second half tends to start a debate about what that emoji means, which a third person can settle.
What do I claim takes five minutes that has never once taken five minutes?
Why ask it
Expect getting ready, a quick stop at one store or 'one more episode.' Laugh along, since he's the one who's been waiting through it, then find out what his own five-minute lie is.
How can you tell I'm hungry before I admit it?
Why ask it
He will know the tell, and you may not: a certain silence, a sudden opinion about where to eat. Useful for both of you, because now he can just hand you a snack.
What's the fastest way to make me laugh when I'm in a bad mood?
Why ask it
If he has an answer ready, he's been studying. If he doesn't, give him one, because it's among the handiest things he can know about you.
What was I wearing the first time we met, or the first time you really noticed me?
Why ask it
Don't expect accuracy. A confident wrong answer is funnier than a right one, and what he does remember, a color or a laugh or where you were standing, is the sweeter detail.
Beach, mountains or city: which do I pick, and what do I complain about once we're there?
Why ask it
The first half is easy and the second is the real quiz. If he nails the complaint, he gets to choose the next weekend away.
What am I weirdly competitive about?
Why ask it
You may think the answer is nothing, and he may have a list. Card games, parking, being right about directions: hear it out before you defend yourself.
If I won a five-minute shopping spree in any one store, which store am I running into?
Why ask it
Count down from three and say the store at the same time. A miss still helps him, since the right store is a birthday hint he didn't have to ask for.
What small, harmless thing am I irrationally afraid of?
Why ask it
Keep it to the funny ones, like moths, balloons or phone calls to strangers. Then trade: he names his, and neither of you gets to use them later.
What would I say is your most annoying habit, and what would I say is your best one?
Why ask it
He's guessing your opinion of him, which flips the quiz. Correct the annoying one gently and confirm the best one loudly.
Cute
What's your favorite thing we do together that costs nothing?
Why ask it
Free favorites are the easiest to repeat, so his answer is a plan for the next flat evening, whether that's a walk, cooking or the couch with separate books.
What do I do that you find cute and I'd be embarrassed to hear about?
Why ask it
Brace yourself for an impression of your concentrating face or of how you talk to dogs. Don't argue with it. Then tell him his.
What's your favorite thing about me that has nothing to do with how I look?
Why ask it
Taking looks off the table makes him work for it, and you tend to get something small, like how you talk to waiters or the way you tell a story. Say one back straight away so he isn't left holding a compliment alone.
When did you first know you liked me, down to the moment?
Why ask it
Ask for the scene: where you both were, what you'd just said. His moment is often one you don't remember at all, which is the nice part.
What did you think on our first date that you kept to yourself?
Why ask it
Usually nerves, or a detail about you he was too shy to mention. Swap answers, since you were both doing the same quiet math across the table.
Which photo of us is your favorite, and why that one?
Why ask it
Have him find it and send it. The reason is rarely that you both look good; more often it's what happened five minutes before or after.
What song makes you think of me, even if it's a strange choice?
Why ask it
It may be something that was playing in a car once, with nothing romantic in the lyrics at all. Put it at the top of a shared playlist and add yours for him.
If you had to retire the nickname you call me, what would the new one be?
Why ask it
If he has no nickname for you, this is where one starts. Veto power is yours, but give the new one a week of trial first.
What's a memory of us that you think I've forgotten?
Why ask it
He gets to be the keeper of something, and you get a small piece of your own history back. If you do remember it, tell him your side of that day.
What's the best date we've had that was never meant to be a date?
Why ask it
You may hear about a grocery run that took two hours or a wait at the tire shop. It tells you he counts ordinary time with you, and it's easy to do again on purpose.
Which thing of mine would you steal if you thought I wouldn't notice?
Why ask it
The hoodie tax usually runs one way, so it's fair to ask. Whatever he names, a blanket, your good pen, your playlist, consider lending it for a week.
If you had to describe me as three foods, which three?
Why ask it
Sillier than it is sweet until he explains his choices, and then it turns sweet. 'Something spicy, something comforting and a wild card' is about the best review available.
Where do you want to take me that you've never taken anyone?
Why ask it
Put a date on it before the conversation moves on, or it stays an idea. The places that come up are rarely fancy: a fishing spot, a diner in his hometown, a hill he used to bike to.
What's the nicest thing I've said to you that I probably don't remember saying?
Why ask it
It's often a throwaway remark, not the speech you planned. Hearing which one stuck shows you what he likes to hear, so you can say it again knowingly.
If the two of us had our own holiday, what date would it be and how would we celebrate?
Why ask it
The date he picks is a clue to which day of yours he treasures. Keep the celebration small enough to really do, then put it in both calendars.
What do my hugs score out of ten, and what would get me to an eleven?
Why ask it
Demand a detailed review. The right response to any score below ten is an immediate retest.
Over text
Which three emojis sum up your day so far?
Why ask it
Guess the story before he tells it. Your wrong guesses are the fun part, and it takes him five seconds to answer between other things.
What's the most recent photo on your phone that needs explaining?
Why ask it
Get the photo first and the explanation second. Screenshots of things he meant to look up later count, and are often the best ones.
What's the view from exactly where you're sitting right now?
Why ask it
A dull desk or a parking lot still puts you inside his afternoon. Send yours back so it's a trade and not a check-in.
What's the most boring thing you've done today, written as a movie trailer?
Why ask it
Refilling a stapler becomes 'one man, one office, no way out.' Reply with the trailer for your own dullest hour, and keep going until one of you is caught laughing at a desk.
What should I have for lunch? You get one answer and no follow-up questions.
Why ask it
Low stakes, and he gets to feel useful from across town. Send a photo of the result, and honor the pick even if it's a gas station burrito.
This or that, one word each: sunrise or sunset, sweet or salty, call or text?
Why ask it
Three in one message keeps it quick enough for a busy day. Guess his answers before they arrive, send yours after, and argue about the one you each got wrong.
Who's the better driver, you or me, and what would a neutral passenger say?
Why ask it
Debates go well by text because nobody can interrupt, so let him build his case. Name the neutral passenger and really ask them.
Which of us is more likely to tear up at a movie, and which movie proves it?
Why ask it
He'll say you, so have the title of the one that got him ready. If he denies it, that's your next movie night chosen.
If you had to save my number under something other than my name, what would it be?
Why ask it
A screenshot is the only acceptable proof that he changed it. Change his in return and don't reveal it until you're together.
What's made you laugh the hardest today, even if it was dumb?
Why ask it
Have him forward it or retell it badly. On a day when nothing has, you know to send something, which is a quiet way of checking how he's doing.
Which meme or GIF is you right now?
Why ask it
Answer in kind and try a rule of no words for the next five messages. Good for a day when he's too busy to type but not too busy to scroll.
What are you having for dinner, and what do you wish you were having?
Why ask it
The wish is the half to keep. Save it, because he's just told you what to suggest the next time you're choosing a place.
What are two true things and one lie about your day?
Why ask it
An old party game that suits texting, since he has time to make the lie plausible. Guess, then send your own three.
Which text of mine have you screenshotted or saved?
Why ask it
If there is one, ask him to send it back to you. You'll learn which kind of message from you he keeps, the funny kind or the kind one.
Quick, no thinking: what's the first word that comes to mind when my name lights up your phone?
Why ask it
Speed is the rule, so give him ten seconds. A food or an inside joke is as good an answer as a compliment, and he's allowed to demand yours on the same clock.
What did you see today that made you think of me?
Why ask it
Send this near the end of the day, and have one ready about him for when he asks back: a dog, a sign with a typo, someone ordering his usual.
How to turn a list of questions into a good hour
Practical guidance for the conversation itself
Where each group works best
In the car
Would you rather and the Funny group suit a drive: nobody needs to look anything up, and the driver can answer without taking his eyes off the road. Read them out yourself if he's driving. Leave the ones that ask for a photo or a demonstration until you've parked.
On a slow evening
Know me and Cute want you both in the same room, because half the fun is watching his face while he guesses your shoe size. Pick five, not twenty. When one question turns into a twenty-minute story, the list has done its job and can go away.
In a text thread
Send one question, not a batch. A single odd question in the middle of a workday reads as you thinking of him; six in a row reads as a survey. The Over text group is written to be answered in a line, a photo or an emoji, so he can reply between other things.
With other people around
Funny and Random are safe in front of friends or family, and other people's answers add to the fun. Keep Cute and Know me for when it's just the two of you: being quizzed on your middle name in front of his friends is fun for nobody but the friends.
Four games to make of the list
Guess first
For the Know me group, type your real answer into your phone before he guesses. One point for a hit, half for close, and then swap: he asks the same question about himself. First to five picks dinner. The swap matters, because a quiz that only runs one way starts to feel like a test.
Predict the pick
Each of you chooses five would-you-rather questions for the other and writes down a prediction in secret. Score a point for every correct one. It's a guessing game about each other dressed up as a guessing game about talking dogs.
Defend it
Take any of the debates, such as the better driver or pineapple on pizza, and give each side sixty seconds without interruption. Then switch sides and argue the other position just as hard. Arguing against yourself is where it gets funny.
One a day
Send one Over text question at about the same time each day for a week, and let him send one back. Stop after the week even if it's going well. A game that ends on a high gets asked for again.
Keeping it light
Answer everything you ask
Go second, but always go. If he's the only one answering, it turns into an interview within a few questions. Your answer is also what gives him something to tease you about, which is half of what he's there for.
When he gives a one-word answer
Don't ask a bigger question; ask a smaller one. 'Which aisle?' 'Snacks.' 'Fine, so what's for dinner on Tuesday?' Funny questions run on detail, and most people need one nudge before they commit to the bit.
When a light question gets a real answer
Sometimes the favorite toy has a sad ending, or the birthday question turns up a birthday that went badly. Put the game down and listen. You can pick the list back up later, and he'll remember that you didn't rush past it.
When a guess stings
Know me questions can miss in ways that feel personal, in either direction. Treat a wrong answer as new information for him, not as proof of anything. If a miss really bothers you, say so once, plainly, on another day.
Skip freely
Not every question fits every boyfriend. If he hates hypotheticals, go straight to the debates; if he's shy about the sweet ones, tuck a single Cute question in among ten silly ones. Nothing here needs to be finished.