Hard Questions to Ask Your Friends
For friends who want questions that are hard to answer: on a late night, on a road trip, or in a game where nobody is allowed to say 'I don't know'. The 84 questions come in six groups, in the order a night tends to go: Would you rather and Dilemmas are hard to choose, No right answer is hard to settle, and About you, About us and One to one are hard to say out loud. Every question has a note on what makes it hard, how to keep it from turning into an argument and whether it belongs in a group or between two people.
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The questions
Each question, and why to ask it
Would you rather
Would you rather know every time someone lies to you or get away with every lie you tell?
Why ask it
A good opener, because the choice says which you fear more: being fooled or being caught. Ask the lie-detector side whether they would still want the power on a birthday, while opening presents.
Would you rather lose every memory you have so far or never be able to make a new one?
Why ask it
One choice costs you your past and the other your future, which is why it turns up in every hard round. Ask the friends keeping their memories which single one tipped it, and ask the other side who they would want beside them on the first morning of knowing nobody.
Would you rather have one friend who would do anything for you or thirty who are fun on a Saturday?
Why ask it
Asked among friends this is a loaded question, and everybody knows it. Let the laugh happen, then ask what 'anything' would have to include.
Would you rather have your search history read aloud to your family or your camera roll shown to everyone at school or work?
Why ask it
Nobody has to prove anything by handing over a phone. Watch how fast people decide, since the quick ones know exactly which of the two they are protecting.
Would you rather redo one day of your past or see one day of your future?
Why ask it
Make everyone name the day before they explain. The day people would redo is often a small regret and not a disaster, and a friend who picks the future should say what they are hoping to find out.
Would you rather be the funniest person in every room or the smartest?
Why ask it
It sounds easy until the room votes on which one each person already is. Keep the vote friendly by having everyone explain why they would want to be the other one.
Would you rather lose every photo you have ever taken or every message you have ever been sent?
Why ask it
People reach for their phones to check what they would be giving up, which is allowed. The split is usually between friends who keep faces and places and friends who keep words, so ask each side for the one item that decided it.
Would you rather never be able to go home again or never be able to leave your hometown?
Why ask it
What makes it hard is that 'home' is a house to some friends and a handful of people to others. Settle which one you mean before the argument starts, then ask the friends who would leave for good what they would go back for if they could.
Would you rather be great at the thing you love and never paid for it, or well paid for something that bores you?
Why ask it
Friends with rent to pay hesitate longer than friends without, and neither side is naive or selling out. The follow-up that opens it up is what the boring job would have to pay, because nearly everyone has a number.
Would you rather never feel embarrassed again or never feel afraid again?
Why ask it
Have each person describe their first week without it. Giving up embarrassment usually comes with a list of things they would finally do, and whoever gives up fear should be asked which fear they would keep if they could.
Would you rather give up your phone for a year or go a year without seeing your friends in person?
Why ask it
Close the loophole early: no borrowing anyone else's phone. Underneath, it asks whether the friendship lives in the chat or in the room, and a group that splits down the middle has learned something about itself.
Would you rather be famous while you're alive and forgotten afterward, or unknown now and remembered for centuries?
Why ask it
One option is a life you get to enjoy and the other is a reward you never see, and that is the difficulty. If it drifts into whether fame is good at all, bring it back with 'known for what?'
Would you rather have everyone you know forget you or forget everyone you know?
Why ask it
Read it slowly, because half the room hears it wrong the first time. One choice is lonely for you and the other is hard on everybody else. Friends who choose to be forgotten often say they would just go and introduce themselves again.
Would you rather hear what every friend honestly thinks of you or have to tell each of them what you think of them?
Why ask it
Say up front that nobody is about to do either. The choice shows who would sooner take a hit than deliver one, which is worth knowing before the group tries any honest questions about each other.
If you had to learn one, would you rather know when you will die or how?
Why ask it
Heavier than it looks, so leave it out when someone in the group has lost a person recently. Choosing when tends to be about planning, and choosing how about trying to dodge it.
Dilemmas
You find a wallet on the sidewalk with four hundred dollars and an ID inside, and nobody saw you pick it up. What do you really do?
Why ask it
The word 'really' is the game. Once everyone has claimed they would hand it back untouched, change the details: forty dollars, four thousand, an owner who looks rich in the photo.
A cashier hands you a twenty too many in change. Does it matter whether it's a big chain or a family shop?
Why ask it
Most people draw a line between the two and then struggle to defend it. Ask who ends up covering the missing twenty in each case, and give the last word to any friend who has worked a register.
A friend shows you a haircut, a tattoo or a song they have already posted, and you think it's bad. Do you tell the truth?
Why ask it
The catch is that it can't be undone, so honesty changes nothing except how they feel. Go around and have each person say what they would want to hear in that spot, which is handy to know about your own friends.
You see a friend's boyfriend or girlfriend holding hands with someone else. Do you tell your friend, talk to the partner first or stay out of it?
Why ask it
Keep it invented and name no real couple. The true disagreement is about how sure you would need to be, and it helps to answer from the other chair: what would you want done if the friend were you?
A friend tells you they scraped a parked car and drove away. Do you keep the secret, push them to own up or tell someone?
Why ask it
Loyalty and fairness pull in opposite directions here, and the stranger with the dented door has no voice in the room. A good second round is how bad the damage has to be before the answer changes.
Most of your class or team has a leaked copy of tomorrow's test. Do you look at it?
Why ask it
'Everyone else did' is the pressure, and saying no means a worse score than the people who cheated. Don't put anyone on trial for admitting they would look. Ask what it would take for them to report the leak.
A friend asks you to tell their parents they were at your place last night when they weren't. Do you cover for them?
Why ask it
'Depends where they were' is the standard dodge, so make each person say where their line is. It gets harder when you add that the parents are calling out of worry and not anger.
You and your closest friend both go for the same job, part or place on the team, and only you are picked. Do you take it?
Why ask it
Nearly everybody takes it, so the live question is what they say to the friend that evening. Flip it as well: would you want a friend to turn something down for your sake?
You promised to keep a secret, and now keeping it means a different friend gets hurt. Do you break the promise?
Why ask it
There is no clean way out, which is why it can fill ten minutes. Stick to a made-up example so no real secret is put at risk, and ask whether a warning with no details counts as breaking it.
A runaway train will hit five people unless you pull a lever that sends it toward one. Do you pull it?
Why ask it
An old philosophy-class puzzle and still a reliable argument. After the vote, change one thing at a time: the one person is a child, the one person is somebody you love, or you have to push with your own hands.
Someone you love needs medicine you cannot afford, and you could take it without being caught. Do you steal it?
Why ask it
Yes is the common answer, so the interest is in the reasons and the limits. Would they do the same for a neighbor, and does the pharmacist's side of it deserve any weight?
Your apartment building is on fire and you have time to get one out: your own pet or a neighbor you barely know. Who is it?
Why ask it
People know which answer sounds right and often feel the pull of the other, and admitting that takes nerve. State one rule before the first person speaks: nobody gets called heartless for either choice.
A button gives you a million dollars, and a stranger you will never meet loses everything they own. Do you press it?
Why ask it
Anyone who refuses at once should be offered ten million, and anyone who presses should be asked about meeting the stranger afterward. The distance between those two versions is the whole question.
If someone in your family did something seriously wrong, would you turn them in?
Why ask it
Leave 'seriously wrong' undefined and let each person set the bar. A friend may have a real situation behind the answer, so accept whatever length of reply you get and don't dig.
You can go back and prevent the worst thing that ever happened to you, but everything that came after it changes too. Do you do it?
Why ask it
No one has to say what the thing was, only yes or no and why. It tends to quiet a room, so ask it late and have something lighter ready for afterward.
No right answer
Which is worse: failing at something in front of everyone or never trying it?
Why ask it
Everybody knows the poster answer. Ask for the last time each person chose not to try, and the slogan turns into a story that is rarely as brave as the first reply.
Do you owe more to the friend you have known longest or to the friend who treats you best?
Why ask it
Both kinds of friend may be sitting in the room, so argue it with a neutral test: one spare ticket and two people who want it. Nobody names names. What you are listening for is whether history counts as a reason or only as a habit.
Do people really change, or do they just get better at hiding who they were?
Why ask it
Friends who go back to childhood will start citing each other as evidence, which is fine while the examples are flattering. If someone brings up a person who hurt them, the question has stopped being abstract and it is time to listen.
What matters more: what you meant to do or what happened because of it?
Why ask it
Give the group something small to argue over, like a surprise party that made the guest of honor miserable. Most fights between friends are this same argument with names attached, so it is good practice.
Is something still wrong if nobody is hurt and nobody ever finds out?
Why ask it
Get an example on the table before anyone takes a side, because people picture very different things. Reading a diary that was left open is the usual test case, and it splits most groups.
Which is worse: doing something wrong, or watching it happen and saying nothing?
Why ask it
Give it a scene everyone has sat through, such as a group chat piling on one person while you read along. Plenty of people have been the silent one, so steer toward what would have made it easier to speak up and away from who is guilty.
Can you forgive someone and still not want them back in your life?
Why ask it
Many people have a real name in mind and won't say it, which is their right. Each answer is a position the person has earned, so nobody suggests a phone call or a reunion.
Does everyone deserve a second chance, and who decides when it has been used up?
Why ask it
Easy to agree with until someone asks about a third chance and a fourth. If two people in the group once fell out with each other, keep the examples far from home.
Would you take a pill that made you content for the rest of your life if it also meant you stopped wanting anything more?
Why ask it
It asks whether happiness is the goal or what you get from chasing other things. A friend going through a rough patch may say yes very quickly, and that calls for a kind word in private later, not a debate in front of everyone.
Would you want to live forever if the people you love still aged at the normal speed?
Why ask it
The condition does the work: without it, most people say yes. If the mood drops, ask which age each person would choose to stay at, a gentler question and usually a funnier one.
How much money would be enough for you to stop wanting more, and do you believe your own answer?
Why ask it
Have everyone write a number down before anyone speaks, or the first figure sets the range. Friends grow up with different amounts of money, so no one comments on whether a number is high or low.
How much of who you are did you actually choose?
Why ask it
Hard because every answer sounds like either a boast or an excuse. Start by having each person give a percentage, which hands them something to defend, and let 'twenty' and 'eighty' explain themselves to each other. It is also the turn toward the honest groups, since everyone has just been talking about themselves.
About you
What is the hardest decision you have ever had to make, and would you make it the same way again?
Why ask it
A fair first honest question, since the person answering controls how much gets told. A friend who says they would decide differently isn't asking to be talked out of it. Ask what they know now that they didn't then.
What do you regret not doing more than anything you did?
Why ask it
Things left undone are easier to say aloud than harm done, which makes this the safer door into regret. If the thing is still possible, ask once what is stopping them and then let it rest.
What is one true thing about you that nobody here knows?
Why ask it
It doesn't have to be a secret. A job they nearly took or a fear of escalators counts, and the size is theirs to pick. Whatever comes out stays with the people who heard it.
What was the last lie you told, and who was it protecting?
Why ask it
Recent lies are mostly small and social, so the first half gets laughs. The second half is harder, because the true answer is often 'me'.
What would you change about yourself if it took no effort at all?
Why ask it
Hold back the 'but we love that about you' for a minute. Ask how long they have wanted it changed, and the reassurance will sound less automatic when it does come.
Which opinion do you keep to yourself because you expect us to judge you for it?
Why ask it
Agree first that the opinion gets heard tonight and debated some other time. It can be a film everyone else worships or a view on religion, and the friend who goes first sets how brave the rest will be.
What mistake do you keep making, knowing full well that it is one?
Why ask it
Texting the same person back, saying yes to everything, leaving it all to the last night. Laughing along is fine. Advice is welcome only if they ask for it.
What criticism of you stung because it was accurate?
Why ask it
Who said it, and are the two of them still on speaking terms? Friends shouldn't treat this as their chance to second the criticism, however right they think it was.
What are you worst at admitting: that you are wrong, that you are hurt or that you need something?
Why ask it
Three choices make it answerable in a word, a help to friends who freeze on open questions. Then ask the others how they can tell when it is happening, because they nearly always can.
What is the meanest thing you have ever said to someone, and do you think they remember it?
Why ask it
Almost everyone has one sentence they can still hear themselves saying. Skip the comforting 'you were only a kid' and ask whether they have ever thought of telling the person.
Who do you owe an apology to, and what has kept you from giving it?
Why ask it
If that person is sitting in the room, the speaker decides whether to say so. Pride, time gone by and not knowing how to begin the message are the usual reasons, and naming the reason is often most of the way to sending it.
What part of your past would you least like to be judged by?
Why ask it
They can name the era and leave out the events: 'ninth grade' or 'the year after I moved' is a complete answer. Friends who were around for it stay quiet unless they are invited to add something.
When did you last feel like a failure, and who knew about it?
Why ask it
One sentence is plenty, and the details are theirs to keep. 'Nobody knew' comes up a lot, and the reply is 'tell me next time', said once and meant.
What is hard in your life right now that you have been making look easy?
Why ask it
Better with three or four people than with eight. This may be the first anyone has heard of it, so thank them before asking anything and check in again during the week.
What about your family is hard to explain to people who didn't grow up in it?
Why ask it
Save it for a small group or a pair, since families are not equally easy to talk about. Offer the pass before asking, and never compare one household with another afterward.
What are you afraid of that you have never said out loud to us?
Why ask it
Whoever asks goes first, with a real answer. A fear told to friends for the first time needs 'that makes sense', not a list of reasons it will never happen.
About us
What first impression of someone here turned out to be completely wrong?
Why ask it
An easy way into honesty about each other, because every story ends with 'and then I got to know you'. Let the person described give their own first impression back.
What excuse have you given this group that wasn't true?
Why ask it
Declare an amnesty before anyone answers, or nobody will. Confessions run along the lines of 'I wasn't sick, I was tired', and after hearing a few, people find it easier to just say they are tired.
What do we do as a group that you go along with and don't much like?
Why ask it
Expect the restaurant nobody chose, the two-hour goodbye or the teasing. The group may reply only with questions tonight, and defending the tradition waits until tomorrow.
What habit does each of us have that the rest of us have quietly learned to live with?
Why ask it
Take one person at a time and keep to habits, never character: always late, never replies, narrates films. The moment the person being described stops smiling, move to the next.
Who here are you least like, and what do you admire about them?
Why ask it
The first half sounds like an insult and the second half stops it being one, so insist on both. Two friends who name each other have usually just explained why they bicker.
What does someone here have that you have been jealous of?
Why ask it
Envy between friends is normal and almost never spoken, which is the hard part. Heard properly it is a compliment, so the person named says thanks and resists listing the ways their life is secretly difficult.
Who here would you call at three in the morning with a real problem, and why them?
Why ask it
Somebody won't be named, and that can sting. Soften it by having each person say what they would call the others for, since the middle-of-the-night friend and the good-news friend are different jobs.
When has one of us hurt your feelings without noticing?
Why ask it
Not for a night when two people are already annoyed with each other. The friend who did it listens and says sorry, and can skip explaining what they meant, because 'without noticing' already grants them that.
What have you held back from telling one of us because you thought it would start a fight?
Why ask it
Answer with the subject only, such as 'something about money', and take the rest to a private conversation with that person. Held to that rule, it clears the air without a scene.
Which of us do you find hardest to say no to, and what have you agreed to because of it?
Why ask it
The friend who gets named is often the last to know. Keep the examples small, like a ride across town or a party you were too tired for, and let that friend say 'you can tell me no' in front of everyone, since it will be put to the test soon enough.
If we all thought you were making a big mistake, would you want us to say so or let you find out?
Why ask it
Remember the answers, because each one is an instruction. Some friends want it said once and then dropped, and some want to be left alone until they ask.
What is most likely to pull this group apart over the next few years, and what would we do about it?
Why ask it
Distance, partners and one person always doing the organizing are the usual suspects. It is only a sad question if it stops at the first half, so stay on it until someone has proposed something practical.
What is the truest thing you could say about each of us in one sentence?
Why ask it
Truest is not the same as harshest, and most friends reach for something they have never said. One sentence per person, and whoever is being described doesn't argue with it.
One to one
What do you know about me that I have never actually told you?
Why ask it
A soft start for two people, because the answers are mostly fond: how you go quiet before bad news, what you order when you're sad. If one is wrong, correct it kindly, since they have been acting on it.
What do you think I would say is your biggest flaw?
Why ask it
Each of you guesses, then the other confirms or corrects. The guess is often harsher than the truth, and finding that out is the reason to ask.
What do you get from other friends that you don't get from me?
Why ask it
Difficult to hear without keeping score. Nobody is one person's everything, and learning that your friend goes elsewhere for football talk or blunt advice takes pressure off both of you.
What do I do that makes me harder to be close to than I need to be?
Why ask it
Only for a day when you are ready for a specific answer, such as changing the subject whenever things turn serious. Say thank you and don't explain the habit. If you want to ask it back, wait a week so it isn't a trade of blows.
Have you ever lied to me, and will you tell me now what it was about?
Why ask it
Agree beforehand that old lies get a pardon. They mostly turn out small and protective, like loving a gift or being busy that weekend. For a bigger one, give yourself a day before deciding how you feel.
When were you angriest at me, and did I ever know?
Why ask it
Often the anger is years old and the friend who caused it never heard a word. Let them tell the whole story before you give your side, and consider not giving your side at all.
When have you felt like my second choice?
Why ask it
New partners, new jobs and new friend groups account for most answers. You can't promise it will never happen again, so ask what would have made that stretch easier and offer that.
What have you wanted to tell me and decided I wouldn't take well?
Why ask it
This one is also about you: it asks what you are like to bring bad news to. Whatever they say, the first test is whether you take it better than they predicted.
What do you think I am getting wrong in my life right now?
Why ask it
You are inviting an opinion, so you don't get to be offended by one. Ask for a single thing, hear it to the end and say you will think about it. Deciding whether they are right can wait.
Is there someone in my life you think is bad for me?
Why ask it
Strictly for two people in private, and never within earshot of the person meant. Your friend may have carried this for months. Ask what they have seen, because examples are more use to you than a verdict.
Which change in either of our lives worries you most for this friendship: a move, a partner, a new crowd or something else?
Why ask it
'We'll be fine', said too fast, closes the conversation. Talk about what staying close would look like in practice, down to how often you would call, and agree on that.
What would have to go wrong for us to stop being friends?
Why ask it
It sounds grim and usually ends up reassuring, because the list is short and neither of you plans to do anything on it. Think of it as a map of what each of you counts as unforgivable.
What is one promise you would like us to make each other tonight and really keep?
Why ask it
A good last question for two. Keep the promise small enough to be kept, such as telling each other within a week when something is wrong, and write it down.
How to ask hard questions with friends
Practical guidance for the conversation itself
Rules to agree on first
Decide where 'I don't know' is allowed
In Would you rather, Dilemmas and No right answer, everybody has to land somewhere. 'It depends' is allowed only if the person then says what it depends on and answers both versions. In About you, About us and One to one the rule flips: anyone can pass, on any question, without giving a reason. Being made to choose is fun, and being made to confess is not.
Hard is not the same as harsh
A hard question is hard for the person answering it. A harsh one is only fun for the people watching. If you can tell that a question would corner one particular friend, about a breakup, a family, a grade or their body, leave it out and nobody needs to know why.
What gets said stays with the people who heard it
No screenshots, no recording, no retelling to the friend who couldn't come. Say it out loud before the first honest question, because people decide how much to tell based on where they think it will end up.
The asker goes first on the honest ones
For the choosing questions, the reader can answer last so they don't steer the vote. From About you onward it is the other way around: if you want to ask it, you answer it first, at about the depth you hope to get back.
Ways to play
The count-of-three vote
One person reads a Would you rather or a Dilemma, counts to three, and everyone holds up one finger for the first option or two for the second at the same moment. Nobody can copy, and nobody can hide. The smaller side explains first, then the larger side, then anyone may switch.
On a road trip
The front passenger reads and the driver votes last. Choosing questions and dilemmas suit a car, since a debate can run for twenty miles and no one has anywhere to be. Keep About you and About us for a stop or for the place you are driving to. The driver shouldn't be the one having a hard conversation.
A late night with four or five people
Two choosing questions to wake everyone up, one from No right answer, then pass the list around and let each person pick the About you question they are willing to answer. Choosing your own hard question feels very different from being handed one. Finish with a single About us question that the whole circle answers.
With your best friend
Take turns choosing from One to one, and both answer before you move to the next. Three questions is a full evening. They are in order from easiest to hardest, so start at the top unless you have had this kind of talk before.
Keeping a debate from becoming a fight
Argue with the answer, never the person
'Why would you press the button?' is fair. 'What does that say about you?' is not. A dilemma is a made-up situation, and what a friend says about a runaway train is not a prediction of how they will treat you.
Change one detail when it stalls
When two sides start repeating themselves, alter one fact and vote again: a bigger sum, a closer person, a chance of being caught. People move when the situation moves, and the point where someone changes their mind is more interesting than who was right.
Put a clock on it
Five minutes a question, then a final show of hands and the next one. Nobody has to be converted. If two friends are still at it, each gets one minute to argue the other's side as well as they can, which usually ends in laughing.
Keep real people out of the examples
The dilemmas about secrets, cheating and covering for someone work because they are invented. Once a real name or a real couple comes into it, the conversation is gossip, and someone who isn't there is being judged. Bring it back to 'a friend' and 'someone'.
When the honest answers land hard
Which questions belong between two people
Anything about one particular friendship, about someone's family, or about what a friend is getting wrong in their life. Criticism heard in front of an audience weighs more than the same words in private, even when the audience is kind. In a group, stick to questions that everyone answers about themselves or about the whole circle.
How to hear something hard about yourself
Say thank you, then stay quiet for longer than feels natural. Ask one question to make sure you understood, and leave the reply for tomorrow. An explanation given straight away sounds like a defense, and it teaches your friend not to tell you next time.
If something serious comes out
Now and then a hard question gets an answer that is bigger than a game: a friend is being hurt, or is thinking about hurting themselves. Stop playing, stay with them, and help them get to an adult they trust or a professional. That is the one case where keeping it among friends is not the kind thing to do.
Finish lighter than the hardest answer
Go back to a Would you rather, ask for the truest sentence about each person, or end on the promise question if there are two of you. People agree to another night of hard questions when the last one finished with everyone still glad they came.