Devious Questions to Ask
Twenty prying questions for a group of friends who already trust each other: the rules you break without guilt, the excuse you invented on the spot, the petty thing you did and the grudge you are still quietly maintaining. Late at night, with people who will not repeat it, and with passing allowed at any point.
The questions
Open any question for the note
What is the smallest rule you break constantly and feel no guilt about?
Why ask it
A safe opener because everyone has one and nobody is incriminated by it. It also sets the register for the rest: small, specific and true rather than a story about being wild.
What is the most devious thing you did as a child and never got caught for?
Why ask it
Childhood puts distance between the person and the deed, so the answers come out fuller than adult ones would. Expect forged notes, hidden vegetables and elaborate sibling framing.
What is a small lie you tell so routinely it has become part of your personality?
Why ask it
The interesting part is why the lie persists once nobody is checking. Answers about running late, having read something, or liking a food usually reveal what the person is trying not to be seen as.
What is the best excuse you have ever invented on the spot?
Why ask it
This one gets performed, which is fine. Ask whether it worked and whether it was ever discovered, because the second half is where the story actually is.
When did you get out of something you absolutely should have had to do?
Why ask it
Reveals how someone operates when a rule is inconvenient rather than important. Watch for whether the answer includes who ended up doing it instead.
What are you unreasonably good at that sounds harmless and is not?
Why ask it
People name skills they are quietly proud of and slightly wary of: reading a room, remembering what you said last month, getting refunds. It tends to explain things the group has already noticed.
Whose group chat would you want to read for one hour?
Why ask it
The choice matters more than the curiosity. Naming a friend group rather than a celebrity says there is something specific they suspect they are not being told.
What is the most petty thing you have done in response to something equally petty?
Why ask it
Escalation stories are funny and revealing, because the size of the original slight tells you what the person cannot let go of. Parking, laundry and shared kitchens dominate.
What have you looked at that you had no business seeing?
Why ask it
Deliberately vague about whose and what, which lets people answer at whatever depth they choose. Anyone who says never has usually redefined the word looked.
What compliment have you given purely to get something?
Why ask it
Small, mercenary and near universal. The follow-up worth asking is whether they think the other person knew, since most people believe their own version was subtle.
What is the most manipulative thing you have done that you still think was justified?
Why ask it
The word justified is what makes this answerable, and the defense is the interesting part. Bad answers here are the ones where the justification arrived long afterward.
Is there a secret you keep for someone else that you wish you did not know?
Why ask it
Asks about the weight of it, not the content, so nobody has to break a confidence to answer. Most people have one and have never described what carrying it costs.
What grudge are you still quietly maintaining, and what is it actually about?
Why ask it
The second clause pushes past the incident toward what was really taken: standing, credit, or an apology that never came. Grudges rarely survive being stated plainly out loud.
What have you got away with at work that would be awkward if it came out?
Why ask it
Keep this to a group with no reporting lines in it. The common answers are inflated timesheets, unearned credit and one email that should never have been forwarded.
What is the most controversial thing you believe that you are willing to say in this room?
Why ask it
The clause about this room matters, because it lets people choose their own limit rather than performing courage. Do not let the group argue the position; the point is what they were willing to say.
When have you let someone keep believing something untrue because correcting it was inconvenient?
Why ask it
Lies by omission are far more common than invented ones and much less examined. Answers often involve a relative, a job title, or something a partner assumes.
What did you do purely for attention, and did it work?
Why ask it
Admitting the motive is the hard half, so the honest answers land as a relief for everyone listening. Expect haircuts, arguments started on purpose and one badly timed announcement.
What is the closest you have come to genuinely serious trouble?
Why ask it
Late in the list because it needs the earlier answers as cover. Watch how the person describes what stopped it, since luck and judgment get confused freely here.
What did you assume about someone in this room that turned out to be completely wrong?
Why ask it
Turns the prying inward and repairs the room rather than damaging it. Being named in a wrong assumption is usually flattering, which is why this works better than asking for a criticism.
What would you least want the rest of us to find out, and why that one?
Why ask it
A closer, and the only question here where passing should be completely unremarked. The reason someone gives for a fear of exposure is often more telling than the thing itself.
How to play this without it going wrong
Practical guidance for the conversation itself
Who this works with
People with history, not new acquaintances
These questions rely on already knowing that nobody will repeat anything. With a group that met last week, the answers will be sanitized versions and the game reads as an interrogation.
No reporting lines in the room
One manager present changes every answer, whether or not they intend it to. Question 14 in particular should not be asked in front of anyone who writes your review.
State the pass rule out loud
Say at the start that anyone can pass on anything without giving a reason, and then pass on one yourself early so it has been demonstrated rather than just offered.
Whoever suggested it goes first
The first answer sets the depth for the whole evening. Going first with something genuinely unflattering is the only reliable way to stop the group trading harmless anecdotes for an hour.
Keeping it moving
- Answer in the first person only. The moment someone starts telling a story about an absent friend, the game has turned into gossip.
- Go around rather than letting the group settle on one person. Three questions in a row aimed at the same guest stops being a game.
- Pick six or seven questions, not all twenty. Interest drops sharply once people are answering out of obligation.
- Let the follow-up be the good part. Did it work, did anyone find out, and would you do it again get more than any new question.
- If an answer kills the mood, stay with the person for a minute before moving on. Rushing to the next question tells them they should not have said it.
Afterward
Somebody usually wakes up regretting one answer. A short message the next day saying you are glad they said it, and that it stays with you, costs nothing and settles it. The reverse also holds: nothing from this evening should reappear as a joke in front of other people, or in an argument three months from now. Groups that break that once do not get honest answers again, and everyone can feel the difference at the next attempt.
What goes wrong
Using a question to make a point
Asking about grudges while looking at the person you have a grudge with is not a game. If you want that conversation, have it separately and without an audience.
Judging the answer you asked for
You cannot invite an admission and then react to it. Even a raised eyebrow ends the honesty for the rest of the evening, and people remember who supplied it.
Pushing a pass
Asking a second time, or teasing someone for skipping, converts a pass into a refusal. Move on immediately and do not come back to it later in the night.
Drinking through the harder half
The last five questions produce disclosures that are hard to take back. If the group is well past sober, stop at question 10 and keep the rest for another time.