Questions to Ask When Your High
Slow, wandering questions for a night when you are high and the conversation has gone quiet. They lean on noticing, remembering and wondering rather than debate, and they work best with people you already trust.
The questions
Open any question for the note
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.
When did you last lose track of time completely, and what were you doing?
Why ask it
The answer is almost never a holiday or a party. It is usually something repetitive and absorbing, which is a quiet way of finding out what a person actually likes doing.
What is a memory that arrives with a smell attached to it?
Why ask it
Smell-linked memories come back with more detail than ones people have told before, so this pulls up stories that have not been rehearsed. Expect a long pause first; that pause is the question working.
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.
What is the last thing that made you laugh so hard you could not stop?
Why ask it
Asking for the last time rather than the funniest thing gets you a real answer instead of a curated one. Most people discover while telling it that it is not funny out of context, and that is usually funnier.
What would you notice about this room if you had never been in it before?
Why ask it
It turns a familiar space into something worth looking at, which is a state people often already half occupy while high. Answers say a lot about what each person pays attention to first: objects, light, mess, or other people.
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 part of your day do you genuinely enjoy but never mention to anyone?
Why ask it
The unmentioned pleasures are the honest ones, since nobody performs a favorite ten minutes of a Tuesday. Answers are small and specific and are often the nicest thing anyone says all evening.
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 something you would like to be good at that has no use whatsoever?
Why ask it
Removing usefulness removes the ambition answer, so you get whistling, juggling, sea shanties, throwing a ball at a wall. It is a much better window into a person than asking about goals.
When did you last change your mind about something that mattered?
Why ask it
Watch for whether the answer is about an argument they lost or something they simply grew out of. People who cannot think of anything are usually being honest, and that is worth sitting with rather than pressing on.
What is the kindest thing someone has said about you that you did not believe at the time?
Why ask it
This asks for the compliment and the disbelief together, which is why it lands harder than asking for the compliment alone. Frequently the person can now see the speaker was right, and saying so is the whole point.
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 do you think you will remember about tonight in ten years?
Why ask it
Turns the evening itself into the subject, and the answers are usually a detail rather than a topic: who sat where, a joke, the weather. It also naturally starts winding the night down.
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 a long, drifting conversation good
Practical guidance for the conversation itself
Set the room up first
People you trust, place you know
Familiar surroundings and familiar company matter more than the questions do. Anxiety in this state is usually about not being sure of the setting or the people, and no amount of good conversation fixes that.
Water, food, and nowhere to be
Have both within reach, and take driving off the table for the evening before anyone starts. A conversation with a departure time hanging over it never gets past the first layer.
Phones down, nothing recorded
People say things in this state they would not post, and knowing a camera is running shuts the whole thing down. If something is worth keeping, write one line in a notes app and put it away.
How to ask these
- Ask one question and then stop talking. The long pause before an answer is where the interesting version comes from.
- Answer your own question too, and go second rather than first so nobody is following your lead.
- Follow the detail, not the topic: ask where they were standing, what time of year it was, who else was there.
- Let the conversation wander off the question entirely. The question was a starting point, not an agenda.
- If someone gives a one-line answer twice in a row, they are done with this mode; switch to something lighter or put music on.
- Do not turn any answer into advice unless you are asked for it.
When to stop
Watch for the turn towards worry
Reflective can slide into anxious quickly, and the tells are repetition, checking a phone, or asking whether everyone else is fine. Change the subject, put on something familiar, get some air, and stay with the person.
Leave decisions until morning
Insights about relationships, jobs and moving cities feel unusually clear right now. Write them down and look at them in daylight; the ones that are real will still be there.
What is said here stays here
Somebody will tell you something they have told nobody. Not repeating it, and not bringing it up the next day unless they do, is the entire price of admission to this kind of conversation.