Questions to Ask High People
Twenty questions for a relaxed evening with friends who are high, running from easy silly openers to more sincere ones later on. Written for whoever is keeping the conversation moving without putting anybody on the spot.
The questions
Open any question for the note
What's the most random thought you've had in the last ten minutes?
Why ask it
Whatever comes out is unfiltered by definition, which is the point. It also sets the register for the rest of the evening, since silly answers invite silly answers back.
What song would you put on right now if it were entirely up to you?
Why ask it
A low-stakes way in, and the choice reveals more than a question about taste ever would. Expect the next ten minutes to become a negotiation about what plays after it.
What's the best thing you've ever eaten at two in the morning?
Why ask it
Late-night food answers are always specific and slightly embarrassing, which makes them useful in a group where people do not know each other well yet.
What did you notice today that you'd normally walk straight past?
Why ask it
This one works because the noticing is real rather than remembered. Answers tend to be small and physical, a texture or a sound, and it shifts the group from talking to looking.
How would you explain what a cloud is to someone who had never seen one?
Why ask it
Explaining something obvious out loud is much harder than it sounds, and it produces genuine comedy without anyone having to be clever on purpose.
What's a film you've never actually watched but have strong opinions about?
Why ask it
Nearly everyone has one, and admitting it is a small confession that makes bigger ones easier later. Expect at least one person to be genuinely offended on the film's behalf.
Which animal would be worst at using a phone?
Why ask it
A silly premise that people take surprisingly seriously. The good part is the arguing about paws and beaks, and it asks no vulnerability from anyone in the room.
What's a rule everyone follows that nobody can actually explain?
Why ask it
This drifts from silly to genuinely interesting on its own: tipping, handshakes, why the bread is at the back of the shop. A good bridge for the middle of the evening.
What did you believe as a kid for far too long?
Why ask it
Childhood beliefs are safe to admit and often turn out to be shared. The answers usually say something about how someone's family talked to them without anyone having to raise that directly.
If your life had a laugh track, when would it go off?
Why ask it
Better than asking about someone's sense of humour, because it forces them to point at real moments in their own life rather than describe a preference.
What's the strangest thing in this room if you actually look at it?
Why ask it
Attention is already wandering around the room, so this puts it to use. Ceiling textures, plug sockets and other people's ornaments all become fair game.
What do you find beautiful that you'd feel a bit silly admitting sober?
Why ask it
Ask this once the group has settled. It is a sincere question wearing a light coat, and the answers, a bus at night, a particular tree, are usually offered without any irony at all.
What's the last thing that made you laugh until you couldn't speak?
Why ask it
People remember these vividly and tell them well. Also useful for cooling things down if the conversation has wandered somewhere heavier than the room wanted.
If you could rename one everyday object, which one needs fixing?
Why ask it
Language questions are funny because everybody has a private objection to some word. Watch for the person who has clearly been holding this particular grievance for years.
What would you tell your fifteen-year-old self about right now?
Why ask it
Gentler than asking about regret, since the frame is a conversation rather than a verdict. What comes out is usually reassurance rather than advice, which says a lot about where someone is.
What's the most certain you've ever been about something that turned out to be wrong?
Why ask it
Being confidently wrong is universal and safe to admit in a relaxed room, and the stories are reliably good. It nudges the group toward honesty without asking for anything heavy.
What do you think you'd be doing right now in a slightly different version of your life?
Why ask it
Not quite a regret question, so it stays comfortable. What surfaces is often the thing the person is actually weighing up at the moment.
What's something you keep meaning to try and never get round to?
Why ask it
Small, answerable and slightly hopeful. If two people name the same thing, something may genuinely get planned, which is a better outcome than most conversations produce.
What do you think people get wrong about you?
Why ask it
Ask late, and only if the group is close. It gives someone a chance to correct an impression they have been carrying around, and it lands very differently at midnight than at a dinner table.
What are you grateful for that you don't say out loud much?
Why ask it
A good closing question. Gratitude spoken aloud in a relaxed room tends to be specific and unperformed, which is why it works far better here than in any formal setting.
Keeping the conversation good
Practical guidance for the conversation itself
How to run it
Start silly and drift
The first three questions should cost nothing to answer. Sincerity turns up on its own an hour later; reaching for it early just produces a pause that the whole group then has to recover from.
Let the silences sit
Answers arrive slowly here and often improve while everyone waits. Filling the gap with a fresh question kills the one you already asked, and people stop bothering to think.
Follow the tangent, not the list
The list is for restarting a stalled conversation, not a running order. If one question turns into twenty minutes of arguing about whether a crow could work a touchscreen, that was the question working.
Read the room
- Leave out anything about work, money, family trouble or health; those questions land badly here and are hard to climb back out of.
- If someone goes quiet or anxious, stop the questions and put music on. Water, food and a calmer room help more than conversation will.
- Do not ask anyone to explain a feeling they are having right now. Ask about last week instead.
- Nothing said in this state gets repeated later or filmed. That is the whole social contract of the evening.
If you are hosting
- Put snacks and water out before anybody needs them.
- Keep the group small. Past about six people, answers get performed rather than said.
- Sort out how everyone gets home in a way that involves nobody driving.
- Let people skip a question without explaining why they are skipping it.