Questions to Ask When High
Questions for a slow evening with friends: sensory ones to open with, funny and curious ones in the middle, a few that go somewhere quieter later. Includes notes on reading the room, keeping things comfortable for anyone feeling anxious, and which questions to leave alone.
Want questions from the whole vault instead? Try the random question generator.
The questions
Each question, and why to ask it
What does this song look like?
Why ask it
A good first question because there is no wrong answer and nobody has to be clever. People answer with colours, weather, rooms, or a specific place, and once someone has said something odd out loud the rest of the conversation gets easier.
What is the strangest thing in this room if you actually look at it?
Why ask it
Anchors the conversation in what is physically around you, which is where attention already is. Everyday objects, plug sockets, door handles, the pattern on a mug, get genuinely peculiar under inspection, and this usually produces the first real laugh of the night.
What food would you want to appear in front of you right now?
Why ask it
Deceptively good, because the answers are vivid and specific and everybody has one. It also tends to reveal comfort foods and childhood ones rather than impressive meals, which opens onto where somebody grew up without asking directly.
What is a word that has always sounded wrong for what it means?
Why ask it
Language goes slippery in exactly this setting, so this one lands well and stays light. Expect people to repeat a word until it stops meaning anything, which is half the fun and needs no follow-up from you.
What is the best texture in the world?
Why ask it
Almost nobody has been asked, and everyone turns out to have a firm opinion: cold sheets, wet sand, a dog's ear. Sensory questions like this are the most reliable way to get a quiet person talking, because they require memory rather than performance.
What smell takes you straight back somewhere?
Why ask it
Smell tends to bring the whole scene with it, so the answers arrive as small stories rather than single words: a grandmother's kitchen, a swimming pool, a particular petrol station. Follow the place rather than the smell and you have twenty minutes.
What did you love as a kid that you have not thought about in years?
Why ask it
Warmer than a general question about childhood and much easier to answer, since it only asks for one forgotten thing. It often produces the detail that makes everyone else remember their own version, which is when a conversation stops being turn-taking.
What is the funniest thing you have ever seen actually happen?
Why ask it
Ask for something witnessed rather than a joke, which rules out repertoire and forces a real memory. Be ready to tell yours first, because the first person to go sets how long the stories are allowed to be.
What is something small you are weirdly good at?
Why ask it
The word small is the important part: it gives permission for parallel parking, whistling, or guessing the time. These answers are more revealing and much more fun than talents, and people are usually pleased to be asked about a skill nobody credits.
What animal would you be terrible at being?
Why ask it
Funnier than the usual version because it invites self-deprecation rather than self-flattery. The reasoning people give is where the humour is, and it stays comfortable for anyone who does not want to say anything about themselves directly.
If your life had a narrator, what would they sound like?
Why ask it
Gets at self-image sideways, and the answers range from a nature documentary to a bored sports commentator. It also tends to become a running joke for the rest of the evening, which is a good sign in any conversation.
What is a rule everybody follows that nobody ever agreed to?
Why ask it
This one gets genuinely interesting: standing a certain distance apart, not talking in a lift, saying you are fine. Expect a slow start and then several answers at once, and be prepared for the conversation to stay here for a while.
What would you do with a completely free day and no phone?
Why ask it
More concrete than asking what someone wants from life, and the answer arrives in real hours rather than ambitions. Notice whether the day they describe is one they could actually have next weekend, since people often surprise themselves with that.
What do you think you will be nostalgic for in twenty years?
Why ask it
Turns nostalgia forwards, which is unfamiliar enough to make people think. Answers usually point at the ordinary parts of now, a shared flat, a bad job, this exact sort of evening, and it tends to make the room fonder of the present.
What is the nicest thing a stranger has ever done for you?
Why ask it
A gentle way to move somewhere sincere without asking anyone to be vulnerable about themselves. The stories are often very small and quite affecting, and this is a good question to reach for if the mood has gone a bit flat or brittle.
What is something you have changed your mind about without noticing?
Why ask it
Harder than it sounds, so leave room for a long pause. What comes out is usually about a person, a place, or a belief someone was raised with. If nobody has an answer, let it go rather than pressing, and move to something lighter.
What do you think about just before you fall asleep?
Why ask it
Quieter and more intimate than it looks, and it lands differently late at night than it would at a dinner table. Answers range from a to-do list to the same memory for years, and it deserves a real pause afterwards rather than an immediate turn to the next person.
Who do you think about more than they would ever guess?
Why ask it
Almost everyone has someone: a teacher, a friend who moved, someone who died. Ask it once and then stop, because the value is in the person's own recognition rather than in an explanation. Some people will just say a name, and that is a complete answer.
What is something you wish people asked you about?
Why ask it
A rare question that improves the rest of the evening, because the answer is a direct instruction about what someone wants to talk about. Then actually ask them about it, which is the part people usually forget to do.
What is the best thing that happened today, even if it is tiny?
Why ask it
Works in any mood and requires no depth, which makes it useful for winding down or for pulling the conversation back if it has drifted somewhere heavy. Insisting on tiny is what stops people from saying nothing much.
What do you think happens after we die?
Why ask it
The one everybody reaches for, and it goes better late, when people are settled, than early. Read the room first: with someone anxious or recently bereaved this is not a fun tangent, and if the answers get uneasy, change the subject deliberately rather than following it further.
What do you want to remember about tonight?
Why ask it
A good closing question, because it asks people to notice the evening while they are still in it. The answers are usually specific and small, and saying them out loud is what makes them stick better than any attempt to summarise afterwards.
What have you noticed in the last hour that you would normally walk straight past?
Why ask it
This one works because it needs no memory and no cleverness, only attention to the room. It also sets the tone for the rest of the night: specific and small rather than grand.
What is a sound you like that nobody thinks of as a nice sound?
Why ask it
Answers tend to be oddly specific and oddly universal at the same time: a dishwasher changing cycle, tires on a wet road. If someone says "birds", ask what kind and where they were standing.
What is a song you know every word of and cannot remember learning?
Why ask it
This produces a list, then usually a performance, and it maps someone's childhood without asking about it directly. It is also the safest possible way to end up singing.
If today had a smell, what would it be?
Why ask it
A soft closer that gets an odd, specific answer and does not demand another story. It also quietly checks in on how everyone's day actually went.
If this room had a laugh track, when would it have gone off in the last ten minutes?
Why ask it
Points the joke at the recent past, which everyone shares, so nobody has to invent anything. It tends to restart a conversation that has stalled without dragging it anywhere heavy.
If snacks were money right now, what would be worth the most?
Why ask it
Reliably produces an argument about exchange rates that nobody wants to win. It also usually ends with someone going to get the snack in question, which is the correct outcome.
What food would be improved by being served the size of a car?
Why ask it
The comedy is in the defense, not the choice, so follow up by asking how it would be eaten and stored. Answers that are already big, like a cake, get less funny, so push for something small.
Which object in this room would be most dangerous if it could move on its own?
Why ask it
Turns the space you are sitting in into the joke and gets everyone looking around. Expect the lamp, and expect at least one person to become genuinely uneasy about the lamp.
If you could make one sound illegal, which one goes?
Why ask it
Gets specific fast, and the answers are usually a shared irritation nobody has said aloud before. Anyone who names a sound in the room right now has won.
What is the worst possible name for a hospital?
Why ask it
Wrong-answer questions like this are easier than clever ones, because there is no risk in a bad attempt. Repeat the best one for the rest of the night and it becomes a running joke.
If your fridge could talk, what would it say about you?
Why ask it
A confession disguised as a joke, which is why it gets honest answers about how someone actually lives. Keep it playful; if a reply lands too close to something real, move on rather than dig.
If you had to swap your hands for two kitchen tools, which do you pick?
Why ask it
The good part is watching people work out the practical consequences of a whisk. It also produces immediate demonstrations, which is where most of the laughing comes from.
Which fictional character would be the worst person to live with?
Why ask it
More productive than asking for the best, because complaints are specific and praise is vague. The best answers are heroes rather than villains, so nudge people away from the obvious monsters.
If you had to fight one animal to keep your job, which one and how does it go?
Why ask it
An old bar argument that still works, mostly because everyone overestimates themselves against a goose. Ask for the plan, not just the animal, and the plan will be the funny part.
Which one of us goes first in a horror movie, and be honest?
Why ask it
Only ask this with people who like each other, since the whole thing runs on affectionate accuracy. Have everyone answer about themselves first, then compare, which takes the sting out of it.
If you had to give a twenty-minute talk with no notes starting now, what is the topic?
Why ask it
Reveals the thing a person actually knows too much about, which is often not what you would guess. Follow it up by asking for the first slide.
If an animal in your life could file a report on you, what would it say?
Why ask it
Funnier and more revealing than asking what someone's pet thinks, because a report implies complaints. People are gently honest about their own habits when the criticism comes from a cat.
What is something everyone treats as normal that would be impossible to explain to someone from two hundred years ago?
Why ask it
The trick is that the obvious answers, phones and planes, are boring, and the good ones are things like tipping, or open-plan offices. Push past the first answer and the conversation gets going properly.
What did you believe as a child that you can still follow the logic of?
Why ask it
This is not the same as a funny misunderstanding; it asks the person to reconstruct their own reasoning, which is a strange and satisfying thing to do out loud. The best answers make everyone briefly agree with a five-year-old.
What did you assume adults understood that it turns out nobody understands?
Why ask it
Answers cluster around money, health insurance and how anybody decides anything, and there is real relief in hearing them said aloud. It works with any age gap in the room, which not many questions do.
What is the strangest thing your body does that you have stopped questioning?
Why ask it
Keeps things physical and slightly absurd without becoming a health conversation. If someone starts describing symptoms that worry them, that is a signal to change the subject rather than diagnose it.
What is a thought you have never said out loud because it sounds stupid?
Why ask it
Only ask this where nobody will be teased for the answer. Given that, it is the point where the conversation stops being pleasant and starts being interesting, so let the silence run before someone fills it.
What is a question you would rather not know the answer to?
Why ask it
Late-night territory: it can go towards mortality, relationships or a test result somebody is waiting on. If the room is heavy or someone is anxious, skip it, and never push for the reason behind the answer.
What's something you understand now that nobody could have told you?
Why ask it
Stays concrete because it asks for one thing. What usually comes back is a lesson the person was warned about and ignored, along with the reason the warning could not land at the time.
When have you come closest to feeling like time stopped?
Why ask it
Everyone has one and almost nobody has said it aloud: a piece of music, cold water, driving at night, holding a baby. The specificity is the whole value of the answer.
Do you think you chose your personality or inherited it?
Why ask it
This starts an argument in most rooms, which is the point. Most people discover they believe both halves at once and cannot say where one ends and the other begins.
What do you believe that most people around you don't?
Why ask it
Phrased this way it tends to avoid politics and land somewhere odder and more personal. If nobody in the room has an answer, the group is less varied than it thinks it is.
Do you think people genuinely change, or just get better at managing themselves?
Why ask it
This splits a room reliably, and where someone lands usually reflects what they have had to forgive, either in themselves or in a parent.
If you met yourself as a stranger, would you like you?
Why ask it
Odd enough to catch people off guard, and the answer is rarely the confident one. It gets at self-regard without anyone having to use the word.
What do you think consciousness actually is?
Why ask it
Nobody knows, which is what makes this a good question rather than an unfair one. It lets people speculate without any obligation to be right, and the speculation is where the evening gets interesting.
What do you hope is true?
Why ask it
A good place to stop. Hope is easier to admit than belief, and the answers to this tend to be the truest thing anybody says all night.
What do you want to come back to when we are both sober?
Why ask it
The best closer available, because the ideas that felt enormous tonight mostly evaporate by morning. Naming one, or writing it down, is how the good part of the conversation survives.
Keeping the conversation good
Practical guidance for the conversation itself
How to ask
- One question at a time, then wait. Long silences are part of the format, not a failure of it.
- Answer your own question too. A question fired at someone with no offer from you feels like a test.
- Follow the specific thing they said rather than moving to the next question on the list.
- Let tangents win. The point is the conversation, not getting through the set.
- Keep the volume of questions low. Four good ones over an evening beats twenty in an hour, which starts to feel like an interview.
Reading the room
Start sensory, not existential
Sound, texture, smell, food, and the objects in the room are easy to answer and put nobody on the spot. Save anything about death or regret for much later, if at all.
Watch for someone getting anxious
If a person goes quiet, tense, or preoccupied, drop the introspective questions entirely and go back to something concrete and mundane. Water, food, fresh air, a familiar film, and a change of subject all help more than talking it through.
Mind the asymmetry
If one person is considerably more affected than everyone else, they are not in a good position to be asked personal questions, and they may not remember answering them. Keep it light with them and revisit anything real another day.
Careful with first-timers
Someone new to this is already managing a lot of unfamiliar input. Questions about mortality, secrets, or whether life means anything are a poor addition.
Questions to leave alone
- Anything asking for a secret nobody has told before. It gets answered more easily than it would sober, and regretted the next day.
- Questions about someone's relationship, family conflict, or money, which are hard to end once opened.
- Anything that puts a person on trial about a decision they have made, however gently it is phrased.
- Health worries, grief, and past trauma, unless the person raised it themselves and clearly wants to talk.
- Follow-up pressure of any kind. A shrug is an answer, and the correct response is to move on.
Practical bits
- Have water and something easy to eat within reach before the conversation starts.
- Put the phones somewhere out of sight. Nothing kills a slow conversation faster than three people scrolling.
- If you want to remember an idea, say it into a voice note rather than trying to hold onto it.
- Sit where people can see each other, and turn the overhead light off. Both change how much people say.
- Decide early that nothing said tonight gets repeated tomorrow, and mean it.