Funny Questions to Ask Friends
Funny questions to ask friends when the only plan is to laugh: at a sleepover, in the back of a car, or in a chat where everybody is bored at once. The 108 questions are sorted into six groups: absurd what-ifs, would you rathers, petty debates, embarrassing stories, who in this group, and a last group written to be typed over text. Each has a note on what makes it land and what to ask next, and the roasts are written to stay kind.
Want questions from the whole vault instead? Try the random question generator.
The questions
Each question, and why to ask it
Absurd
How many second graders would it take to beat you at tug of war?
Why ask it
The first number is usually too low, and it climbs once someone points out that second graders do not get tired and do not play fair. Have each friend commit to a figure before the arguing begins, then let the group revise it for them.
What is the worst thing to say when returning a borrowed car?
Why ask it
The winners are short and calm, along the lines of 'So, how attached were you to the mirror?' Go around twice, because the second lap is where people stop being polite.
If you had to hide a full-grown giraffe from your family for a weekend, where does it go?
Why ask it
Plans fall apart at the neck, which is the fun of it. Play the suspicious parent and ask one practical question per plan: what it eats, what the neighbors see, how it got upstairs.
A truck delivers ten thousand ping pong balls to your home by mistake and refuses to take them back. What do you do?
Why ask it
Hardly anybody says 'throw them away', and that tells you something about your friends. Listen for the split between those who fill a room for the joy of it and those who immediately start a business.
If you were a professional wrestler, what would your ring name and finishing move be?
Why ask it
Ask for the name first and the move second, since the move is where people start acting it out. Friends are allowed to overrule a name that is too flattering and assign a more accurate one.
What would be the worst possible moment to get the hiccups?
Why ask it
A quick one that needs no cleverness, only a scene: a wedding vow, a driving test, a game of hide and seek. Build a ranking as the answers come in and argue about first place.
If animals could leave online reviews, which one gives humans a single star, and what does the review say?
Why ask it
Pigeons, cats and geese all have a case. Ask for the review word for word, in the animal's voice, and have a second friend write the reply from management.
What is the least reassuring name you could give an airline?
Why ask it
Works in a car, in a line or at an airport gate, though maybe not on the plane itself. The names that land are modest, such as 'Probably Air', and the slogan makes a good second round.
If you had to open a shop that sells only the last thing you bought, how is business?
Why ask it
The last purchase is usually something dull like socks, gas or a single banana, and the dullness is the joke. Push for details: the name over the door, the opening hours, the one loyal customer.
Which cartoon character would be unbearable to sit beside on a ten-hour flight?
Why ask it
The specifics of the flight do the work: the armrest, the snacks, the singing. Once there is a clear worst, flip it and ask which character would be the ideal seatmate, which is harder than it sounds.
If you swapped bodies with a house cat for a day, what is the first thing you would knock off a table?
Why ask it
It skips the usual 'what would you do' and goes straight to the crime. Cat owners answer with an eerie level of detail, so ask them whose glass it is and whether eye contact is maintained.
If your handwriting were a font, what would it be called?
Why ask it
Friends who have seen the handwriting get a vote, and their names for it are harsher: 'Doctor in a Hurry', 'Ransom Note Light'. Have everyone write the same sentence on paper as evidence.
How would you explain your phone to someone from the year 1400 without being accused of witchcraft?
Why ask it
Every explanation makes it worse, which is why this runs long. Have one friend play the villager and interrupt with nervous questions. 'A small glowing window with everyone's faces in it' rarely calms anybody down.
If the fire alarm had to be replaced with a song, which one clears the building fastest?
Why ask it
There are two schools of thought: a song so loud it works as an alarm, and a song so disliked that people leave on their own. Whoever names a friend's favorite band has started a second argument on purpose.
Which two products should never be sold as a two-in-one?
Why ask it
Toothpaste and orange juice is the kind of answer you are fishing for. It rewards the quiet thinker among your friends, so leave a pause, and then ask what it says on the bottle.
If you had a time machine that could only go back ten minutes, what would you use it for?
Why ask it
Ten minutes is too short to fix anything that matters, so people spend it on snacks, comebacks and unsending a text. The comeback crowd will then tell you the exact argument they are still replaying.
What would you be given a lifetime supply of if the universe wanted to annoy you?
Why ask it
Answers are tiny, personal irritations: paper straws gone soft, single socks, a pen that almost works. Friends who know each other well can guess on one another's behalf, and the guesses are often more accurate.
If your town put up a statue of you for the least impressive thing you are known for, what is the statue doing?
Why ask it
People start with something mild, like a statue of them looking for their keys. Open it to the others, who will have a more truthful pose in mind, and finish by asking what the plaque says.
Would you rather
Would you rather your thoughts ran as subtitles for a day, or your camera roll played on a big screen at a party?
Why ask it
Most people pick the camera roll and then remember what is in it. Ask how many photos they would need to delete first, as a number and nothing more.
Would you rather be chased by one angry goose every morning or have a seagull steal your lunch every day?
Why ask it
It comes down to cardio against hunger. Anyone who has met a goose in person tends to choose the seagull without hesitating, and their goose story is worth asking for.
Would you rather only be able to enter rooms by cartwheel or leave them by moonwalk?
Why ask it
Walk people through their week with it: the classroom, the dentist, a first date, a very small bathroom. Then take a vote on which friend could pull off each option.
Would you rather have a laugh that sounds like a car alarm or a sneeze that sounds like a duck?
Why ask it
Demonstrations of both are the whole game. Count how often each would go off in a normal day before anyone locks in an answer, and remember that funny friends make the laugh a real risk.
Would you rather speak only in song lyrics for a day or only in movie quotes?
Why ask it
Test it on the spot by having the person order a pizza under their chosen rule. That quickly separates the friends who know three songs from those with a quote for every occasion.
Would you rather be followed by a referee who whistles whenever you are wrong or a parrot that repeats the dumbest thing you said that day?
Why ask it
The referee is louder, but the parrot has a memory and an audience at dinner. Ask each friend what the parrot would be saying tonight, and let them choose the sentence themselves.
Would you rather let your parents pick your outfits for a month or let your friends choose your profile picture for a year?
Why ask it
The answer depends on what the friends have saved, so this is really a question about trust. If someone chooses the profile picture, describe the one you would use and offer them a chance to change their answer.
Would you rather be the funniest person in a boring room or the most boring person in a hilarious room?
Why ask it
Slower than most would you rathers, since people have to decide whether they want to perform or be entertained. Performers take the boring room in a heartbeat. Ask which room they think they are in right now.
Would you rather have a friend in this room answer all your texts for a week or choose all your meals?
Why ask it
Meals sound safer until people look around at who would be choosing. Each person names the friend they would trust with each job, and the nominees describe the first text they would send or the first dinner they would serve.
Would you rather relive your most embarrassing moment once a year or watch it performed as a school musical?
Why ask it
The musical means an audience, a cast and a catchy song about it, which makes it the braver choice. Ask who plays them and what the big number is called. Nobody has to say what the moment was.
Would you rather always arrive ten minutes early with wet hair or exactly on time wearing one shoe?
Why ask it
It sounds easy until someone asks which shoe is missing and whether hopping counts as arriving. Run each choice through a real week: an exam, a wedding, a first day at a new job.
Would you rather have a phone that is always at four percent or a charger that is always two inches too short?
Why ask it
Painfully realistic, so expect groans before laughs. People who already live at four percent will say so with pride, and a quick battery check around the room shows who they are.
Would you rather have every photo of you for a year taken mid-blink or mid-sneeze?
Why ask it
Mid-blink looks sleepy and mid-sneeze looks like a painting of a disaster. Have everyone pull the face they think theirs would be, then decide which one goes on the school or work ID.
Would you rather be able to talk to dogs or understand what babies are complaining about?
Why ask it
The dog side assumes dogs have a lot to say, and the skeptics will argue it is all 'ball' and 'when'. Anyone with a baby brother, sister or niece picks the babies for practical reasons.
Would you rather have to high-five everyone you meet or bow to them?
Why ask it
Act out a morning under each rule, bus driver and school principal or boss included. Bowing sounds dignified until someone brings up a crowded hallway.
Would you rather be stuck on a long car ride with three copies of yourself or do a group project with them?
Why ask it
Underneath, this asks what you are like to deal with. People who dread the car ride know they talk too much, and people who dread the project know nobody would start it until the night before.
Would you rather have a nose that honks when squeezed or ears that wiggle whenever you lie?
Why ask it
The honk is a party trick, but the ears put an end to every surprise party and every 'I love it' said over a bad gift. Have each friend name one small fib the ears would have caught this week, on the scale of 'I'm five minutes away'.
Would you rather narrate everything you do in the third person or have a stranger follow you and do it through a megaphone?
Why ask it
Narrating yourself sounds manageable until you picture announcing 'and now our hero pretends not to see the neighbor' with the neighbor right there. Have each person narrate their next sixty seconds as a trial run.
Petty debates
How many fries can you take from a friend's plate before you owe them an apology?
Why ask it
Get a number from each person before anyone explains, because the range is wild. Then ask whether asking first changes the count, and whether the law is different for the last fry on the plate.
If you lend a friend a hoodie, how long before it legally becomes theirs?
Why ask it
Somebody present is wearing or storing the evidence, so expect a guilty silence first. Settle the number of months, then whether washing it once counts as giving it back in spirit.
If you say 'we should hang out', are you now responsible for planning it?
Why ask it
The planner of the group will take this personally and deserves the floor. A good ruling ends with a real date on the calendar, which makes this the rare debate with a useful result.
When can you call shotgun: when the car is in sight, when you leave the building, or the night before?
Why ask it
Most friends live under unwritten shotgun law and nobody agrees on what it says. Write the ruling down once you have it. The driver gets a veto, and tall friends will ask for an exemption.
Does the person in the middle seat get both armrests, or is it every elbow for itself?
Why ask it
Almost everyone agrees the middle seat deserves both, and almost nobody behaves that way. Confessions from the window and aisle people come first, then the tactics for winning an armrest back.
Does a sandwich cut into triangles taste better than one cut into rectangles?
Why ask it
Triangle people believe it with their whole hearts and cannot explain why. Ask the other side whether they would send a triangle back, and whether cutting it at all is the real mistake.
How long after a show comes out is it fair to talk about the ending?
Why ask it
Answers run from a weekend to never, and the friend who is three seasons behind has a personal stake. Agreeing on a rule now saves a real argument later, so treat the verdict as binding.
Is it acceptable to quit a board game you are clearly losing?
Why ask it
Someone present has done it and someone else has not forgiven them, so let both sides testify. Then widen it: is letting a friend win on purpose kinder, or worse?
Does the five-second rule depend on the food, the floor or who is watching?
Why ask it
Everybody has a private version of this rule, and it bends a long way for the last cookie. Name specific cases, a grape in the kitchen and a chip at the bus stop, and watch the standards fall apart.
If a friend hands you their phone to show you one photo, how many swipes are you allowed?
Why ask it
The strict side says zero, and most of that side has swiped once 'by accident'. Rule on the harder cases: whether zooming in counts, and what to do about the notification that drops down while you are holding it.
Is it acceptable to sit on a bed in the clothes you wore outside?
Why ask it
There is no middle ground, and people are shocked to learn which side their friends are on. Ask the strict side whether guests are told the rule or quietly judged.
How many sneezes in a row do you keep saying 'bless you' for?
Why ask it
Plenty of people have a firm cutoff they have never said out loud, and it tends to be lower than they expect. Whoever sneezes in sets of six can describe what it is like when the blessings stop.
Which is worse: someone walking slowly in front of you or someone walking right behind you?
Why ask it
Fast walkers and slow walkers are natural enemies, and most friendships contain both. Have everyone show their normal walking pace across the room and let the others judge.
Does the volume have to be set to an even number, a multiple of five, or does it not matter?
Why ask it
Looks trivial until one friend admits that an odd number makes them uneasy and another says they have never once looked. Find out who is sitting at 17 on purpose.
Can you call a movie your favorite if you have only seen it once?
Why ask it
The purists demand repeat viewings and at least one line quoted from memory. It leads neatly into asking each person for the film they have seen the most times, which is rarely the one they call their favorite.
If someone has already pressed the elevator button, is pressing it again an insult?
Why ask it
Short enough for a wait, ideally at an elevator. Pressers call it habit and the offended call it a comment on their competence. The crosswalk button falls under the same law.
When someone says 'guess what', do you have to guess?
Why ask it
Guessers call it good manners, and the other side says 'what?' and waits. Test it live by saying 'guess what' to the friend with the strongest opinion and watching what they do.
Should pets have human names like Kevin, or is that confusing for everyone?
Why ask it
A dog called Kevin is funny for reasons nobody can pin down, which is the heart of the matter. Collect the best human name for a pet from each person, then the worst pet name for a human.
Embarrassing stories
What is the most awkward 'you too' you have ever said back to someone?
Why ask it
The waiter says 'enjoy your meal', and out it comes. Nearly everybody has one, so it warms people up without asking anyone to confess much. The best versions involve a birthday or a flight.
Have you ever called a teacher Mom or Dad, and how did the class take it?
Why ask it
It has happened to enough people that the stories arrive quickly. Ask how long it took to live down. Any teachers or coaches among your friends can report what it is like from the other side.
What is the most solid object you have walked straight into, and what distracted you?
Why ask it
Glass doors and lampposts lead the field. The distraction is half the story, because it is usually a phone, a dog or somebody worth impressing. The three seconds afterward are where the comedy is.
What have you gotten stuck in, on or under, and who had to get you out?
Why ask it
Childhood supplies most of these: railings, playground equipment, a sweater that was too small. The rescuer is the detail to chase, since being freed by a firefighter and being freed by a laughing cousin are different stories.
What song were you caught singing at full volume, and who caught you?
Why ask it
Car windows and headphones are behind most of these, because the singer is sure nobody can hear. Ask which line they were on when they noticed the audience, and expect it to be sung again as evidence.
What is the worst thing your phone has ever done out loud in a quiet room?
Why ask it
Alarms in exams, videos that start by themselves, a voice assistant answering a question nobody asked. The phone takes the blame, so the story is easy to tell. What matters is whether they silenced it or pretended it belonged to someone else.
What did you say or do on a video call when you thought you were muted or off camera?
Why ask it
Most stories are harmless: singing, snacking, talking to a pet. Let people choose their own example and do not dig for a worse one, especially if coworkers or classmates are present.
What is the longest you have kept walking the wrong way because turning around in public felt embarrassing?
Why ask it
The classic cover is the fake phone check before turning back, and some people simply go around the whole block. Ask for their own move, and for a demonstration of it.
What was your most public fall, and did you jump up fast or stay down?
Why ask it
Falls are funny once the teller is clearly fine, so stick to the kind that only bruised pride. The reaction is the punchline: the instant bounce, the 'I'm okay' to nobody, the bow.
When have you turned up dressed completely wrong for the occasion?
Why ask it
Costumes at a party that was not a costume party, a suit at a barbecue, pajamas on the wrong school day. The story is in how long they stayed, so find out whether they went home to change or decided to own it.
What test, tryout or audition did you fail in the most memorable way?
Why ask it
Driving tests dominate, usually with an examiner who went very quiet. Enough time has to have passed for it to be funny, so each person picks their own failure. How many attempts it took in the end is part of the story.
What were you caught doing as a kid that had no reasonable explanation?
Why ask it
Small children run experiments: cutting their own bangs, burying a remote, painting the dog. The teller usually still cannot say why. Ask what the adult who found them said first.
What is the most awkward thing you have said or done in front of a friend's parents?
Why ask it
Best when the friend in question is present and can supply the parents' side of the story. Old sleepovers and dinner tables are ideal territory. Some of those parents still bring it up, and the friend will know.
What is the worst possible place you have gotten the giggles, and who started it?
Why ask it
Assemblies, ceremonies and serious talks from a teacher are the classic settings. Often another friend was the cause, and if that friend is in the room the story gets told from two angles.
What happened the last time you tried to look cool and it went wrong?
Why ask it
The word 'last' keeps it recent and small: a missed high five, a chair that rolled away, a wave at a stranger. Tell yours first, and play it for the slow-motion details.
What old post, caption or status of yours would you pay to have erased?
Why ask it
Old accounts are a museum of bad jokes and deep song lyrics. Agree before asking that nobody goes looking for the evidence without permission, since the laugh should belong to the person telling it.
What is the worst photo of you that someone here still has on their phone?
Why ask it
The keepers will smile before anyone speaks, which answers the question. Describing the photo is funnier than showing it, and the person in it decides whether it comes out.
What small, harmless moment from years ago still makes you wince when it pops into your head?
Why ask it
Usually it is one sentence said to one person who has certainly forgotten it. Hearing three or four of these in a row is oddly comforting, since nobody remembers anybody else's. Wait until everyone has already told a story or two.
Who in this group
Who here is most likely to trip over nothing on a perfectly flat floor?
Why ask it
Start the pointing here, because the accused usually agrees. Count to three, have everyone point at once, then ask the winner for their most recent example.
Who here laughs at their own joke before reaching the end of it?
Why ask it
Affectionate by nature, since a person who cannot finish a joke is good company. Hand them a joke to tell right now and time how far they get.
Who takes the longest to tell a short story?
Why ask it
The winner will try to defend themselves and prove the point in the process. Give them thirty seconds to describe their morning and see whether they make it past breakfast.
Who in this group is the worst at whispering?
Why ask it
Nearly every set of friends includes one person whose whisper carries across a room. Test the field by having each friend whisper the same sentence from the same distance. Tease the volume, never what was said.
Who here is most likely to say 'I'm not hungry' and then eat half of someone else's food?
Why ask it
The accused will blame whoever ordered too much. For a fair trial, ask who has lost the most food to them over the years and what the damage adds up to.
Who is most likely to text 'on my way' while still in bed?
Why ask it
Usually a unanimous vote, and the winner knows it. Have them translate their other phrases: what 'five minutes' means, what 'leaving now' means, what 'almost there' means.
Who has the worst sense of direction, and what is the evidence?
Why ask it
'Evidence' asks for a story, and there is always one about a wrong exit or a parking garage. Let the accused tell it themselves, because their version includes why it was the map's fault.
Who here cries hardest at animated movies, and which one finished them off?
Why ask it
A roast that lands as a compliment, so use it when the teasing needs softening. Several people usually claim the title for themselves, and each will name the exact scene that did it.
Who would leave on a five-minute errand and come back with a new best friend?
Why ask it
Pure praise dressed as a tease, for the friend who talks to everyone in line. Ask the others for the strangest place that person has ever struck up a conversation.
Who is most likely to come home with an animal nobody agreed to?
Why ask it
Follow the vote with the two questions that matter: which animal, and what the excuse sounds like. 'It followed me' is the standard defense. Whoever lives with the winner may want to say a few words.
Who is most likely to begin a sentence with 'fun fact' and be wrong?
Why ask it
Confidence is what gets teased, so it stays friendly as long as someone remembers the times the facts were right. The most memorable false one is worth digging up, since somebody present will still half believe it.
Who here cannot keep a straight face, and can we test it right now?
Why ask it
This one becomes a staring contest: pair off, hold eye contact, first to laugh is out. The person voted most likely often wins out of sheer determination, which is funnier.
Who would win if the whole group played hide and seek in a furniture store?
Why ask it
Small friends are the favorites until someone mentions the patient one who would lie in a display bed for four hours. Worth asking who would give up and head to the food court.
Who in this group would be the worst getaway driver?
Why ask it
The case against each candidate is the fun part: stops for snacks, obeys every speed limit, cannot reverse out of a driveway. Keep it to driving style and let the nominee reply.
If this group ran a summer camp, who leads the hike, who tells the ghost story and who is caught raiding the snack cupboard?
Why ask it
Handing out several roles means nobody is the only target. The arguments happen over the hike leader, since half the candidates would get everyone lost. Once the staff is settled, give the camp a name and a motto.
If a photographer told this group to 'act natural', what would each of us be doing in the photo?
Why ask it
Take one friend at a time and let everybody else answer, then stage the photo for real. Whoever was predicted to be looking at the wrong camera usually is.
If this group had a yearbook, what would each of us be voted most likely to do?
Why ask it
The classic superlatives game, and it works best when every title is oddly specific, like 'most likely to miss a flight while standing at the gate'. Make sure each person gets one before anyone gets a second.
What should each person here never be put in charge of?
Why ask it
The answers are small jobs: the directions, the booking, the candles on the cake. Each comes from a real incident, so ask for it. Close by naming what each person should always be in charge of.
Over text
What does your phone write if you type 'My friends are' and let predictive text finish the sentence?
Why ask it
No effort required and usually nonsense, which is ideal for a bored chat. Everyone posts their sentence unedited. Other openers keep it going, such as 'This weekend I will' or 'The secret to life is'.
Which song title describes your day so far?
Why ask it
One line to answer, so even the friend who never replies can manage it. It tends to start a chain, and a chat that was silent an hour ago ends up building a very odd playlist.
Which emoji do you use in a way it was never meant for?
Why ask it
Every chat has private meanings, such as the skull for laughing or a random vegetable for agreement. Collect them, and consider pinning the dictionary for whoever joins later.
What is your most-used GIF or sticker, and what does it say about you?
Why ask it
Answering means sending it, which gets images moving in a quiet chat. Friends should feel free to answer the second half on each other's behalf.
What is the last thing you took a screenshot of, and did you ever look at it again?
Why ask it
Camera rolls are full of screenshots taken with great purpose and never opened since: a recipe, a pair of shoes, a message to show someone. Allow a pass, because some of them are of this very conversation.
What is the strangest thing saved in your notes app right now?
Why ask it
Notes apps hold shopping lists, half a poem, a parking spot from two years ago and one sentence with no context. Each person picks a note they are happy to share and pastes it exactly as written, typos included.
What is the strangest name you have saved a contact under, and does that person know?
Why ask it
Names like 'Do Not Answer' and 'Kyle Maybe' turn up. In a group chat everyone will immediately ask what they are saved as, so have yours ready.
What has autocorrect made you say that you had to explain afterward?
Why ask it
Ducks feature heavily. The stories with a boss, a teacher or a grandparent on the receiving end are the keepers. Leaving the typos in while telling it over text is part of the charm.
Who in this chat types like a lawyer, and who types like they are falling down the stairs?
Why ask it
The evidence is a scroll away, which is why this roast only works in writing. Quote a recent message to make the case. Both styles are being admired, and the full-punctuation friend will reply with a period.
At what length does a voice message become a podcast?
Why ask it
Ask everyone for a number in seconds, then ask who in the chat holds the record. The record holder is welcome to respond by voice message.
What is your honest reason for reading a message and answering it two days later?
Why ask it
The truthful answer is nearly always 'I replied in my head'. Good for a chat with one famously slow replier, provided the tone stays teasing. Skip it if someone has gone quiet for reasons that are not funny.
Which three rules would a new member need to learn before joining this chat?
Why ask it
The rules describe the chat as it is in practice: never ask where to eat, do not mention the trip, mute it on Sundays. Each has an incident behind it, and newer members finally get to hear the story.
What one-line review would a stranger leave after reading this chat for a week?
Why ask it
Makes everyone scroll back to see what the week was about, which was probably an argument over where to eat. 'Two stars, they never did pick a restaurant' is the tone. Asked on a Sunday, it turns into a weekly recap the chat starts to expect.
Which three-word text would cause the most panic if it landed in this chat right now?
Why ask it
'Check your email' and 'who told you' are the style to aim for. It is funniest when everybody posts an entry at the same moment. Make sure nobody sends theirs to a different chat by accident.
What is the worst possible first text to send someone you have not spoken to in five years?
Why ask it
An invention game, so nobody has to confess anything. The strongest entries are casual to the point of alarm, like 'hey, random question, are you still tall?' Vote with reactions.
What is the least believable excuse you could text for being an hour late?
Why ask it
The job is to write the excuse out in full, with commitment and specific details. A flock of geese and an unexpected parade are fair game. For a bonus, the chat judges which fake excuse its author has come closest to using for real.
Which message in this chat's history do you most wish you could unsend?
Why ask it
Sends people scrolling through years of typos, bad takes and predictions that aged poorly. Screenshots of the offending message are encouraged when it is your own. Leave other people's alone unless they laugh first.
How bored are you right now, on a scale from 'fine' to 'reading the back of the shampoo bottle'?
Why ask it
Made for the afternoon when the whole chat is bored at once. Each friend invents their own top of the scale, and those inventions are the answers worth having. Once everyone has a rating, somebody has to propose a plan.
How to get a group of friends laughing
Practical guidance for the conversation itself
Picking the right kind of question
When everyone is bored
Boredom wants something with no setup and no right answer. Start with Absurd or Would you rather, where the first reply can be one word and the argument takes care of the next ten minutes. The giraffe, the ping pong balls and the goose need nothing but the people present.
Around a table or in a car
Petty debates suit any place people cannot walk away from. Take a show of hands before anyone gives a reason, then let the smaller side speak first. In a car, the driver rules on ties.
With one friend
Leave out the pointing questions, which need a crowd, and use Embarrassing stories. With two people each story gets a proper telling, and trading one for one keeps it even.
With friends you have only just made
Hold the roasts and the old photos until there is some shared history to draw on. Absurd questions and would you rathers ask for imagination only, so a new friend can be funny without giving anything away.
Funny questions to ask friends over text
Send one and answer it yourself
A question dropped into a chat with no answer attached looks like homework. Post it with your own reply underneath, so the next person only has to beat it.
Choose questions with short answers
A typed answer wants to be a line or less. The Over text group is written for that, and most would you rathers and petty debates travel well too. Embarrassing stories lose their timing when typed, so keep them for a call or a room.
Use what the chat already has
Turn a debate into a poll, let reactions do the voting on invented answers, and ask for the GIF or the screenshot when a question calls for proof. A chat that is sending pictures is awake.
Let it breathe
Replies arrive over hours, and that is fine. A second question asked before the first has run out splits the chat into two half-conversations. One a day is plenty, and a regular one, such as the weekly one-line review, becomes something people wait for.
Keeping the roasts kind
Point on three
For any 'who here' question, count down and have everyone point at once. Nobody can follow the crowd, the result is instant, and a split vote is the funniest outcome.
Tease what people do, never what they are
Being late, losing chargers and telling long stories are fair game, because the person can laugh and carry on doing them. Looks, money, grades, relationships and anything a friend is trying to change are not material.
Give the accused the last word
The winner of a vote always gets to respond, and the response is usually better than the vote. A roast that its target finishes stays a shared joke.
Spread the titles around
If one friend has won twice in a row, switch to a question that hands a role to everybody, such as the summer camp or the yearbook, or to one where the winner is being praised, like the animated movies or the five-minute errand.
If a question falls flat
Nobody answers
Give your own answer, short and a bit stupid, and try a different kind of question. Friends who will not invent things will often argue, and friends who will not argue will often tell stories.
A petty debate gets heated
The fries and the borrowed hoodie can touch real grievances. Announce a ridiculous verdict, such as settling it by tug of war, and change the subject while people are still laughing at the ruling.
A story costs more than expected
Sometimes a memory turns out not to be funny to the person telling it. Thank them, drop the follow-up and offer a small embarrassing story of your own so the attention moves on.
One person is doing all the talking
Would you rathers fix this, because everybody has to choose. Go around in order, and ask the quietest person for their reason first.