Funny Questions to Ask
Funny questions to ask people at family dinners, on road trips with friends and in group chats that have gone quiet. They are sorted into silly, hypothetical, embarrassing, debates and random, and each group runs from easy to harder. A last group holds fun questions to ask someone you do not know well yet, where the aim is an easy answer and not a joke.
This set also feeds the Question of the Day.
The questions
Each question, and why to ask it
Silly
Which kitchen utensil do you think has the biggest ego?
Why ask it
Nobody has a prepared answer, which is the point. Expect a surprisingly heated case against the whisk, and ask what the humble spatula thinks of all this.
What two animals should swap sounds?
Why ask it
Short enough to ask anyone, including kids. The best answers come with a demonstration, so request one: a mooing pigeon is funnier performed than described.
What song should play every time you open your refrigerator?
Why ask it
Mundane settings make any song absurd, and a fridge is as mundane as it gets. People who answer instantly have clearly thought about their own theme music before.
If your shoes could talk, what would they complain about first?
Why ask it
A gentle way to let people make fun of themselves. You learn who walks everywhere, who never unties their laces and who owns a pair they have been meaning to replace for years.
What would a documentary about your morning routine be called?
Why ask it
Titles force people to be concise, so the jokes arrive fast. Follow up by asking who narrates it, which tends to reveal how dramatic they think their mornings are.
What is a word that sounds like an insult but is completely innocent?
Why ask it
Works best in a group, because one answer triggers five more. Let people try their word on each other in a stern voice. Skip it if anyone present is likely to push past innocent.
Which vegetable looks like it is hiding something?
Why ask it
Pure nonsense, which makes it a good test of whether someone will play along. The ones who commit to a full theory about the artichoke are the ones to sit next to at dinner.
What would you name a boat if your only goal was to make the whole marina groan?
Why ask it
An open invitation to puns, so aim it at the person who loves them. Everyone else gets to groan, which is its own kind of participation.
What is the least intimidating name you can think of for a motorcycle gang?
Why ask it
Tough image, soft name: the contrast carries the joke. Good for groups because people build on each other, and the winning name usually gets adopted as the team name for the night.
What mythical creature would make the worst roommate, and what is the first house rule it breaks?
Why ask it
Asking for the broken house rule pushes people past naming a dragon and into specifics. Listen for whose answer sounds suspiciously like a real former roommate.
If your sneeze had a catchphrase, what would it be?
Why ask it
Everyone knows what their own sneeze sounds like and nobody has ever been asked about it. Best with people who know each other, since half the fun is friends correcting the answer.
How would you describe your dancing on an official form?
Why ask it
Bureaucratic framing makes people describe themselves with a straight face, which is where the comedy is. Offer an example to get them going, such as 'enthusiastic, structurally unsound'.
What noise do you make when you get up from the couch, and when did that start?
Why ask it
The second half is what gets the laugh, because everyone remembers the year the noise arrived. Lands better with anyone old enough to have a noise. Children will just look at you.
What is the fanciest possible way to describe the last thing you ate?
Why ask it
Turns a granola bar into a tasting menu. It rewards the theatrical person in the group, and you can keep it going by having someone else guess what the dish really was.
What would a museum exhibit about your bedroom floor be called?
Why ask it
A roundabout way of asking how tidy someone is without sounding like a parent. The honest answers involve the phrase 'mixed media'. Ask what the centerpiece of the collection would be.
Which of your belongings would be the first to turn on you if objects came to life?
Why ask it
People answer with the thing they have neglected or mistreated, so it doubles as a confession. The printer comes up a lot. Ask what it would say in its opening statement.
What would your job title be if it described what you really do all day?
Why ask it
Works for students, parents and retirees too, since everyone has an unofficial role. An answer like 'Senior Finder of Lost Shoes' tells you more about a person's day than their real title does.
What award would the people you live with give you that you would rather not win?
Why ask it
A self-roast that stays affectionate, because the awards are for small crimes: Most Lights Left On, Longest Shower, Worst at Replacing the Toilet Roll. If the household is present, they will happily hand out a few more.
What would your villain name be if your evil power came from your worst habit?
Why ask it
A self-roast with a cape on it. People pick the habit they are already comfortable joking about, so it stays light. Let the group suggest names for anyone who gets stuck.
If your life had a laugh track, which moment from this week would have gotten the biggest laugh?
Why ask it
Hardest of the silly ones because it needs a real memory, so give people a second. It gets you an actual story instead of a one-liner, and usually a slightly painful one.
Hypothetical
If you had to carry one piece of furniture everywhere you went for a year, which would you choose?
Why ask it
A quick sorting of the practical from the chaotic. Some people pick a folding chair and consider the matter closed, others commit to a grandfather clock and accept their fate. Ask how they would get it onto a bus.
If every door announced your arrival like royalty, what title would it give you?
Why ask it
People reach for a grand title and then undercut it, which tells you how they see themselves. Good early in a gathering, because the titles stick for the rest of the evening.
If you could only use one facial expression for a whole day, which would cause the least trouble?
Why ask it
Ask them to demonstrate it and hold it while someone else answers. 'Least trouble' makes them think through a dentist visit, a job interview and a surprise party, all with the same face.
If you became mayor of a town populated entirely by geese, what would your first policy be?
Why ask it
Absurd premise, real personality test. Some negotiate with the geese, some flee, some immediately take the side of the geese. Worth asking what their campaign slogan was.
If ordinary errands were professional sports, which one would you go pro in?
Why ask it
Fresher than asking about hidden talents, because everyone has one errand they are smug about. Parallel parking and grocery bagging champions will identify themselves with no modesty at all.
If you had to enter a talent show tomorrow with no time to practice, what would your act be?
Why ask it
No time to get good, only time to commit: the deadline is the joke. If the mood is right, ask for a ten-second preview. If not, a description is plenty.
If you were a ghost with only petty powers, how would you haunt a house?
Why ask it
Removes the horror and leaves the mischief. Answers like moving the scissors or unpairing socks tell you exactly what drives that person mad in their own home.
If you got a parade in your honor but the theme had to be ridiculous, what would it celebrate?
Why ask it
A sneaky way of asking what small achievement someone is proudest of. The best answers are tiny victories, like finally returning a library book. Ask what the lead float looks like.
If you had to wear one costume to every formal event for the rest of your life, which would you pick?
Why ask it
'Formal' is the word that matters, because they have to picture the costume at a wedding. People split between the comfortable option and the one that makes the best entrance.
If you had a superpower that only worked on Tuesdays, which one would still be worth having?
Why ask it
The Tuesday limit forces a bit of planning, and the planners in the group reveal themselves by scheduling their whole week around it. Ask what happens at midnight if they are mid-flight.
If you were shrunk to the size of a grape, which room in your home would be the most dangerous?
Why ask it
Makes people tour their own house in their heads, and the answers get vivid quickly. Pet owners tend to realize the real threat is not a room at all.
If you had to live inside a board game for a week, which one would be the most miserable?
Why ask it
Asking for the most miserable option is funnier than asking for the best. People get oddly specific about rent, dice and being sent back to the start. Follow with which game they would survive.
If you had to give a lecture on the most trivial subject you know far too much about, what would it be?
Why ask it
Everyone is an accidental expert in something, like the plot of one cartoon or the layout of one grocery store. Let them give the first minute of the lecture. They will want to.
If your ten-year-old self ran your life for a day, what would be for dinner and what would go wrong?
Why ask it
Nostalgia becomes comedy with the 'what would go wrong' clause. Expect dessert for dinner and a missed appointment. It also shows what kind of kid they were without asking directly.
If you could make one harmless thing illegal purely out of spite, what would it be?
Why ask it
Pet peeves arrive in their purest form. 'Harmless' and 'spite' give people permission to be unreasonable, so nobody needs to justify banning whistling. Ask what the penalty is.
If aliens landed and you were the first human they met, how would you accidentally embarrass the species?
Why ask it
People answer with their most reliable social failing: the overlong handshake, the nervous joke, offering snacks too soon. Self-aware and affectionate, so it suits mixed company.
If you had a butler for one day but could only give him absurd tasks, what would he be doing?
Why ask it
The restriction stops people from answering 'laundry' and being done. You find out who wants a butler for drama, such as being announced at the grocery store, and who just wants grapes peeled.
If you had to win an argument using only interpretive dance, which argument would you pick?
Why ask it
Two questions in one: what they argue about, and how they move. The best follow-up is asking to see the opening gesture. Expect a reenactment of a long-running dispute about the dishwasher.
If you had to be stuck in an elevator with a mime, a magician or a ventriloquist, who would you choose?
Why ask it
A three-way choice gets faster answers than an open question, and everyone has a firm position on at least one of these. Ask which of the three they think would crack first.
If a cooking show made you compete using only what is in your fridge right now, how doomed are you?
Why ask it
A fridge inventory disguised as a game. You will hear about the half jar of pickles and the mystery container. Harder than it looks, since it requires honesty about condiments.
Embarrassing
What was your first email address or screen name, and how does it feel to say it out loud?
Why ask it
Low-stakes embarrassment with a built-in time capsule. The usual formula is a hobby plus a string of numbers. Go first with yours and the rest of the table will follow.
What did you spend time practicing in the mirror when you were younger?
Why ask it
Easy to answer because the shame is mild and long expired. Autographs, award speeches, a raised eyebrow and one specific dance move all come up. If the group is comfortable, ask whether they can still do it.
Have you ever confidently gotten into the wrong car, and what happened next?
Why ask it
Confidence is what makes it a story: the seatbelt was on, or a conversation had started, before anyone noticed. Ask who was more startled, them or the driver. Anyone who has been the driver has an equally good version.
What do you do when you still have not heard what someone said after asking them to repeat it twice?
Why ask it
Asking a third time feels impossible, so the interest is in the escape. People confess to a laugh, a nod and a hope that it was not a question. Ask about the time it was a question.
What is the most ridiculous thing you ever did to impress a crush?
Why ask it
Pretending to love a band or a sport is the standard confession. Keep it to the distant past if partners are present, and then ask the important question: did it work.
What phase did you go through that you hope no photos survived from?
Why ask it
Broad on purpose, since a phase covers music, slang, clothes and an entire personality. Let people volunteer details at their own pace. The ones who still defend the phase are the most entertaining.
What is the clumsiest thing you have done in a place that was supposed to be silent?
Why ask it
Libraries, exams, weddings and recitals all qualify, and the silence is what makes each story worse. Good for groups, because the memory of trying not to laugh is contagious.
What is the worst message you ever sent to the wrong person or the wrong group chat?
Why ask it
A modern classic of mild horror. Most stories are harmless, like a grocery list sent to a manager. Let people skip it if they go pale, because some wrong-chat stories are not funny yet.
What is the worst answer you have given after being called on when you were not listening?
Why ask it
The bluff is the key ingredient, so ask how long they kept it going before someone noticed. Works well among coworkers, since it lets senior people admit that they drift off in meetings too.
Have you ever pretended to know a book, band or show to keep a conversation going, and how did it end?
Why ask it
The ending is where the comedy is: a narrow escape, or a direct question they could not answer. It also quietly tells the room that admitting you do not know something is fine tonight.
What is the least heroic way you have ever injured yourself?
Why ask it
Steers away from serious accidents and toward the ankle sprained stepping off a curb. Anyone who leads with a sports injury is usually hiding a better story involving a sofa.
What basic skill did you have to secretly look up far later than you would like to admit?
Why ask it
Answers range from boiling an egg to reading an analog clock. It is embarrassing in a relatable way, and once one person admits theirs, the rest of the room gets honest quickly.
What is the silliest thing someone has caught you doing when you thought you were home alone?
Why ask it
Usually a full concert performance or a conversation with the cat. Keep the tone light and take the first answer offered. Best among friends who will respond with their own version.
Have you ever grabbed the hand or arm of a stranger you mistook for someone you knew, and what did they do?
Why ask it
Supermarkets and crowded platforms are the usual settings, and the childhood version, reaching up for the wrong parent's hand, counts too. The stranger's reaction is the punchline, so ask for the look on their face.
What is the longest you have called someone by the wrong name before it became too late to fix?
Why ask it
A slow-burn embarrassment that can run for years. The best answers involve elaborate avoidance strategies. Ask whether the other person ever found out, and whether they are in the room.
What have you broken at someone else's house, and did you own up to it?
Why ask it
Check that the owner is not at the table before asking. The object is rarely the story. What people tell is the cover-up: the quiet repair, the vase turned to face the wall, the years of silence. Now and then someone decides tonight is the night to confess.
What were you sure you were good at until you saw or heard a recording of yourself?
Why ask it
Singing, dancing and public speaking lead the confessions. It needs a bit of trust, so save it for later in the conversation, and add that recordings are unkind to everyone.
What is the pettiest reason you have ever been close to tears?
Why ask it
Pettiest keeps it from getting heavy: a dropped sandwich, a printer, a game lost to a younger sibling. If someone offers something that sounds real, take it seriously and move gently on.
What is the longest you kept up a small lie because correcting it felt too awkward?
Why ask it
Think of the coworker who believes you love hiking. Put it last in a round of embarrassing questions, since it asks for the most honesty. Ask if the lie is still running today.
Debates
Does a movie count as watched if you slept through the middle of it?
Why ask it
A low-stakes argument nearly everyone has a side on. The sleepers defend themselves fiercely. Settle it by asking whether they could explain the plot to a jury.
Is saying you are on your way a lie if you have not put your shoes on yet?
Why ask it
Separates the literalists from the optimists in about four seconds. Couples and roommates already have a history with this one, so stand back and let them present evidence.
Which form of potato is the best, and which one is coasting on its reputation?
Why ask it
Someone has to insult a beloved potato, and the second half of the question makes sure of it. Reliable with any age group, and nobody leaves without having defended mashed.
Is it acceptable to open a snack in the store before you have paid for it?
Why ask it
One side is appalled that anyone does this, and the other does not see the problem, since they were always going to pay. Ask whether the ruling changes for a crying toddler, or for grapes sold by weight.
Is replying with just a thumbs-up polite or quietly hostile?
Why ask it
Splits the room in ways people do not expect. It is useful information as well as a debate, since you will find out how your own replies have been landing all this time.
What is ruder: arriving at a party ten minutes early or forty minutes late?
Why ask it
Hosts and guests answer differently, so ask who in the group has hosted recently. The numbers are chosen to make it close. Someone will insist early is the greater crime, and any host will back them.
Who should control the thermostat: whoever pays the bill, whoever is coldest or whoever gets there first?
Why ask it
Offering three candidates keeps it from becoming a two-person standoff. Expect roommates and families to cite real incidents. Skip it if a real thermostat dispute is currently underway.
Is it acceptable to clap when the plane lands?
Why ask it
Opinions are instant and oddly passionate. The clappers say gratitude, the opposition says the pilot cannot hear you. A good one for travel days and airport waits.
What is the correct number of morning alarms, and is hitting snooze a character flaw?
Why ask it
One-alarm people and seven-alarm people cannot comprehend each other, which is why it works. Anyone who shares a bedroom with a snoozer will need a moment to compose themselves.
How many toppings can you add before a salad stops being a salad?
Why ask it
A fresher cousin of the old sandwich arguments. The debate always ends up at a bowl of croutons, cheese and chicken with one leaf in it. Ask for the exact leaf-to-topping ratio.
Is it fair to eat the last slice without asking if it has been sitting there for an hour?
Why ask it
A question of ethics dressed up as a question about snacks. People propose surprisingly detailed rules about time limits and announcements. Notice who has clearly been a victim.
Which day of the week is the most overrated, and which one deserves more respect?
Why ask it
Friday gets attacked more often than you would think, and Tuesday finds unexpected defenders. It reveals people's work schedules and moods without asking about either.
Does the cook choose the music, or does the person washing the dishes?
Why ask it
Household politics in miniature. The answer shows whether someone thinks privileges come from effort or from suffering. Ask what happens when the same person does both.
What is the fair punishment for watching the next episode without the person you were watching with?
Why ask it
Treat it as a sentencing hearing and ask for proposals. Guilty parties go quiet or plead that they rewatched it and acted surprised. Particularly lively with couples and siblings.
Is looking up the answer in the middle of a trivia argument cheating or justice?
Why ask it
Some people want the truth and some want the argument, and this sorts them. The follow-up is whether there should be a waiting period before anyone reaches for a phone.
Should a birthday last a day, a week or the whole month?
Why ask it
Birthday-month people will reveal themselves with pride. Ask them to justify it to the person at the table who forgets their own. It stays friendly because nobody's mind is ever changed.
Are leftovers really better the next day, or is that a story we tell ourselves?
Why ask it
Needs specific dishes to get going, so ask for the one food that improves overnight and the one that should never be reheated. Chili and fries tend to be the closing arguments.
Which is worse: a wet sock or a wet sleeve from washing your hands?
Why ask it
Two tiny miseries, evenly matched. It works because everyone can feel both immediately. Let people nominate a third contender, like a seatbelt that locks when you lean forward.
Which seat in the car is the best on a long trip, and who has earned it?
Why ask it
Years of family road trip grievances come up with 'who has earned it'. Tall people, carsick people and navigators all make their case. Ask who always ended up in the middle.
Should you tell someone you just met that they have food in their teeth?
Why ask it
A real etiquette dilemma, so it gets more considered answers than the rest. Wanting to be told is common, and so is dreading the telling. Ask people to demonstrate their discreet signal.
Random
What inanimate object have you apologized to most recently?
Why ask it
Asks people to admit to something they do without noticing. Door frames and chairs come up a lot. The ones who deny it will catch themselves doing it within the week.
What is the funniest thing you have overheard a stranger say with no context at all?
Why ask it
A storyteller's question. The missing context is the joke, so resist the urge to work out what the stranger meant. People who ride buses and trains have the best material.
What is the strangest thing in your junk drawer, and why can nobody throw it away?
Why ask it
A junk drawer collects the things nobody decided to keep, which is why the answers are good. Expect a key to an unknown lock, a cable for a device long gone, a single birthday candle. Ask how many house moves it has survived.
What is the most ridiculous name you ever gave a toy, a pet or a car?
Why ask it
Naming logic from childhood is reliably unhinged: a hamster named after a vegetable, a bear called Bear. Ask who in the family objected. Works across every age at the table.
What nickname did you have that you never agreed to?
Why ask it
What you want is the origin story, so ask who started it and whether it is still in use anywhere. Let people keep an unkind one to themselves. Most are simply baffling.
What song lyric did you sing wrong for years, and what did you think it said?
Why ask it
The misheard version is nearly always funnier than the real one, and people will sing it for you. It rarely needs a follow-up, since everyone else is already waiting to share theirs.
What is the most creative insult a child has ever aimed at you?
Why ask it
Children insult with total sincerity and no sense of proportion, so the results are odd and specific. 'You look like a tired potato' tends to stay with a person. Parents, teachers and older siblings have the deepest archives.
What did you think adults did all day when you were a kid?
Why ask it
Children's theories about jobs, bills and meetings are wonderfully wrong. It also slips in a second question, which is how the reality compares. The answer to that is usually a sigh.
What is the funniest reason you have ever been late to something?
Why ask it
Asks for an excuse that happened to be true. A goat in the road, a locked bathroom, a wrong building. Works well at the start of a gathering, ideally aimed at the last person to arrive.
What rule did your family have that you later found out no other family had?
Why ask it
Everyone assumes their household was normal until they eat dinner at a friend's. The rules people report are small and oddly specific, like no singing at the table. Ask when they discovered the truth.
What is the dumbest way you have ever gotten lost?
Why ask it
Dumbest lets people tell the story against themselves, which keeps it light. The best ones happen close to home or with directions in hand. Ask who they blamed at the time.
What is the worst thing you have ever cooked, and who had to eat it?
Why ask it
The victim is the important part, so ask whether that person has ever let them forget it. Salt mistaken for sugar leads the confessions. A natural one for the dinner table.
What is the most ridiculous thing you have bought only because it was on sale?
Why ask it
Bargain logic makes fools of everyone, and the item is usually still in a closet. Ask whether it has ever been used. The proudest shoppers and the most sheepish give equally good answers.
What is the most absurd thing you have ever argued about with someone you love?
Why ask it
Looking back at a ridiculous fight is one of the few ways arguing becomes funny. Couples often answer together and then restart the argument, so be prepared to referee.
Which relative would be the funniest contestant on a reality show, and which show would it be?
Why ask it
Casting is the fun part: the uncle on a survival show, the grandmother who would quietly win a baking contest and then judge the judges. Relatives who are present will dispute their casting. Good at holidays, for obvious reasons.
What idea seemed brilliant to you late at night and ridiculous the next morning?
Why ask it
Business plans, haircuts, messages to old friends and furniture rearranged at midnight all qualify. It takes a bit of humility, since the idea was theirs alone. Ask how far they got before morning arrived, and whether anything was ordered.
What completely trivial opinion would you be willing to defend in front of a judge?
Why ask it
Invites a rant, which is a gift to the right person. The courtroom framing keeps it theatrical and not angry. Give them one minute for an opening statement and let the group rule on it.
Who can make you laugh with just a look, and what is the look?
Why ask it
A warm one to mix in among the embarrassing material. The look always has a history, often a classroom or a family dinner where laughing was not allowed, so ask where it started. If that person is present, expect a demonstration.
What have you seen a hundred times that still makes you laugh every time?
Why ask it
A reliable laugh says more about a sense of humor than a recent one does. It might be a film scene, a family video or one photo of a dog. Phones will come out, so allow time for a screening, and laugh even if you had to be there.
What would the opening line of your autobiography be if its only job was to get a laugh?
Why ask it
The hardest of the lot, since it asks for an original joke on demand. Give people time, or let them workshop each other's. The line they land on is usually more honest than they planned.
Fun
What is the best smell you can think of?
Why ask it
Anyone can answer in a few words, and no one has to be clever. Rain on hot pavement, a bakery first thing, the inside of a new book: each one comes with a place, so ask where it takes them.
Which season are you at your best in?
Why ask it
Asks about the person and not the weather, which is why it beats asking for a favorite season. Autumn people tend to have a speech ready. Find out what they do with the season they like least.
What do you always buy when a long drive stops for fuel?
Why ask it
Road snacks are a ritual, and people are loyal to theirs to a degree that surprises them once they say it aloud. Useful to know before sharing a car with someone.
What is the best sandwich you have ever had, and where were you?
Why ask it
The second half matters more than the first. A great sandwich is nearly always attached to a trip, a hungry afternoon or one particular counter, and that is the story you are asking for.
What show do you put on when you cannot decide what to watch?
Why ask it
A comfort show is a better guide to someone than the series they recommend. Plenty of people know theirs by heart, so ask which episode they would show a newcomer.
Which animal would you most like to see in the wild?
Why ask it
Easy for children and adults alike, and it slides into travel without anyone asking about travel. Follow up with how close they would be willing to get.
What is your karaoke song, or the one you would pick if there were no way out?
Why ask it
The escape clause lets people who would never sing still answer. You hear what someone thinks their voice can manage, which is rarely what their friends think.
Which board game or card game are you hardest to beat at?
Why ask it
Permission to boast about something that does not matter. Many families have one game that was retired after an incident, and whoever caused it is usually the one answering.
What was the first album or song you bought with your own money?
Why ask it
It dates a person to within a few years, and they are seldom proud of it. Someone young enough never to have paid for a song can name the first one they played on repeat.
What game did you play outside as a kid that you would still join in with today?
Why ask it
Street and playground games had local names and local rules, so two people from different towns will compare notes for a while. The rule that caused all the arguments is worth hearing about.
What is the best thing about the place you grew up?
Why ask it
People complain about a hometown easily and praise it rarely, so expect a pause and then something fond: a beach, a bakery, a bus driver who knew everyone. It works just as well with someone who never left.
Which instrument do you wish you had learned?
Why ask it
A wish with almost no regret in it, so it stays light. Listen for the reason, since nobody wants to play the cello in general: they want one song, or one moment at a party.
What is the oldest thing you own that you still use?
Why ask it
It takes a moment of thought, and then out comes a pan, a coat or a mug that has outlasted several homes. Ask who had it before them.
Which place have you visited that you would go back to tomorrow?
Why ask it
Different from a favorite trip, because tomorrow rules out anywhere that was only good once. Small towns and one particular cafe beat famous cities more often than you would guess.
What is the best thing you have ever found by accident?
Why ask it
Left wide open on purpose: a restaurant down the wrong street, a band, money in a winter coat, a friend. What someone counts as a find tells you what they prize.
What would you do with a free afternoon and no phone?
Why ask it
Taking the phone away is what makes it a question. Some people have a plan in two seconds, and others realize aloud that they are not sure, which is a good conversation too.
What is the next thing on your calendar that you are glad is there?
Why ask it
Gives you something to ask about the next time you see them. If the calendar looks empty, shrink it to this week: a meal, a game or an early night all count.
What is the best present you have been given that cost almost nothing?
Why ask it
Ruling out price leaves the thought, so the answers are a drawing, a mixtape, a ride to the airport at an awful hour. Warm without getting heavy, and it works at any age.
Which holiday tradition would you keep if you could only keep one?
Why ask it
Any holiday will do, so nobody is left out. The choice is rarely the big meal. It tends to be something small and slightly odd that one household does and no other, and people enjoy explaining it.
When did a stranger last go out of their way for you?
Why ask it
Needs a real memory, so allow a pause before anyone speaks. The stories are short and involve a lost wallet, a flat tire or a hard day, and the room is usually warmer once two or three have been told.
How to ask a funny question and get a funny answer
Practical guidance for the conversation itself
Setting up the laugh
Start silly, save embarrassing for later
Open with a question from the Silly group, where there is no wrong answer and nothing to confess. Embarrassing questions need a warm room, so hold them until people have already laughed at something together.
Fun questions to ask before the funny ones
With a person you have only just met, even a silly question can feel like an audition. Begin one step earlier, in the Fun group: a best smell or a first album takes one sentence to answer, and nobody has to be witty. Two or three of those, and the Silly questions land far better.
Go first when the question asks for a confession
If you want someone's first screen name, offer yours. A story told against yourself shows the group what size of embarrassment is expected, and that nobody will be mocked for matching it.
Ask it with a straight face
Deliver an absurd question as though it were a serious one. Do not announce that it is funny, and do not laugh before the other person answers. The deadpan is what gives them permission to commit to a ridiculous answer.
Chase the detail, not the next question
The first answer is rarely the funny part. Ask what happened next, who saw it, or what the goose mayor's campaign slogan was. One question followed up properly beats several asked in a row.
Three ways to use the list
Round the table
- 1Pick one question from the Silly or Hypothetical group and read it out.
- 2Everyone answers in turn, and the person who asked goes last.
- 3The group picks the best answer, and whoever gave it chooses the next question.
- 4Stop while people are still laughing, not when the answers start to slow down.
Debate court
- 1Choose a question from the Debates group and split the room into two sides by seat, not by opinion.
- 2Give each side one minute to argue its case, including the people who privately disagree with it.
- 3Appoint one judge, who must rule and must give a ridiculous reason for the ruling.
- 4Rotate the judge and pick a new question.
Group chat slow drip
- 1Post a single question with no explanation and give your own answer right away.
- 2Let replies arrive over the day, and hold the second question until the first has run dry.
- 3Keep the Embarrassing group for chats where everyone knows each other in person.
When it goes wrong
The question gets silence
Some questions simply miss. Answer it yourself in one sentence, then move to a different group of questions. Repeating it louder or explaining why it is funny has never rescued one.
Someone looks cornered
Embarrassing questions are only funny when the teller chooses the story. Make passing normal by saying at the start that anyone can skip or swap a question, and never let the group answer on someone's behalf.
The laughs turn on one person
Teasing drifts from the story to the person quickly. If the same person has been the punchline twice, aim the next question at yourself or switch to a hypothetical, where nobody's past is on trial.
A debate stops being a joke
Arguments about potatoes can uncover real household grievances. When the voices change, rule in favor of whoever is losing, declare the matter closed and move to a Silly question.
One person answers everything
Keen answerers are an asset until nobody else speaks. Direct the next question by name to someone quieter, and pick an easy one so they are not put on the spot.