Fucked Up Questions to Ask Someone
Twenty questions for one person rather than a group, where there is nobody to hide behind: what they lie about, who they cut off, what they recognise from a parent and dislike, and the choice they hope they are never asked to make.
The questions
Open any question for the note
What do you lie about most often?
Why ask it
Most is the useful word, because it asks about a habit rather than an incident. The common answers, being fine, being on the way, having read the thing, are small enough to admit and honest enough to start from.
What do you do when nobody is watching that you would not want filmed?
Why ask it
Broad enough to answer with something harmless and open enough to answer with something real, so they choose the depth. Where they set that line is itself the information.
What do you think people misjudge about you, and are they wrong?
Why ask it
The second half stops it becoming a complaint about being misunderstood. Anyone who says the judgement is partly fair is being genuinely honest, and the conversation gets better from there.
What is the opinion you hold that you would never post?
Why ask it
It gets at self-censorship rather than politics. Some people name something contentious, others realise they have nothing they would not publish, and both answers say a lot about how they live.
Who have you cut off without ever explaining why?
Why ask it
Almost everyone has done this and almost nobody describes it as cruelty. Whether they think the person deserved an explanation tells you how they will end things with you.
What is the cruellest thing you have said out loud, and did you mean it?
Why ask it
The follow-up carries the weight, because a line said in temper and a line said deliberately are different admissions. People who still remember the exact wording have not put it down.
What is the worst thing you have done to someone who did not deserve it?
Why ask it
The clause rules out the revenge stories people are comfortable telling. Expect a long pause, and let it run rather than rescuing them with a smaller version of the question.
What have you done that you would do again, knowing the damage?
Why ask it
It separates regret from resolve, which most confession questions blur together. Answers usually involve leaving someone, and the lack of guilt is what makes them worth hearing.
What do you envy in someone close to you?
Why ask it
Envy about a stranger is easy, and about a friend it is uncomfortable, which is the point. The specific thing they name is often what they think is missing from their own life.
When did you last feel relieved by someone else's bad luck?
Why ask it
Common, rarely admitted, and usually about work or a comparison to a peer. Saying it out loud tends to defuse it, and the reaction to being asked is as telling as the answer.
What is the worst thing you would forgive in a partner?
Why ask it
It maps their actual limits rather than their stated ones. A very high tolerance can mean generosity or it can mean a history of accepting too much, and the follow-up should find out which.
What part of yourself do you recognise from a parent and dislike?
Why ask it
Specific, hard to dodge, and it usually produces the most self-aware sentence in the conversation. Anyone who has never noticed anything is telling you something about how they view their family.
What is the thing about you that ends relationships?
Why ask it
Asked as a fact rather than a possibility, which is why it works. Someone who blames only their exes has answered it accidentally and completely.
What do you avoid thinking about at night?
Why ask it
It asks about avoidance rather than about the thing itself, which is a much easier door to open. Health, money and one particular person cover most answers.
What is the closest you have come to a decision you could not have undone?
Why ask it
Deliberately unspecific so they can choose how much to say, and the near miss is usually more revealing than a completed act. Take whatever level of detail they offer and do not press for more.
What have you never told anyone, and what stops you?
Why ask it
The second half is the answerable half, and it is fine if that is all they take. Naming the fear, judgement, consequences, someone else being hurt, is a real answer even without the secret.
What would you change about how you were raised, if you could?
Why ask it
It invites criticism of a family without asking anyone to condemn their parents. The size of the change asked for is the measure: a small one often means more than a sweeping one.
What do you think you would do if you knew you had a year left?
Why ask it
The useful version of this question is the gap between the answer and their current life. Anything they name that they could start next month is the part worth talking about.
What is the choice you hope you are never asked to make?
Why ask it
It reaches the fear directly without requiring a confession, and the answers are usually about caring for someone or choosing between two people. Nobody answers this one flippantly.
What would you want said honestly at your funeral, even if it stung?
Why ask it
A closer that turns everything before it into something constructive, because it asks what they want to be true. Compare it with the earlier answer about what ends their relationships and the conversation finishes itself.
Asking these one to one
Practical guidance for the conversation itself
What makes it work
Answer before you ask
One on one there is no group to dilute the attention, so an unanswered question is an interrogation. Give your own answer at the same depth you are hoping for and the whole thing becomes a trade.
Say why you are asking
One sentence is enough: you want to know them properly, or the conversation has been too polite for too long. Without that, heavy questions read as a test.
Let the silence sit
The pause after a hard question is where the real answer is assembled. Filling it with a softer rephrasing tells them you would rather they took the easy version.
Follow one answer instead of moving on
The list is a starting point, not a schedule. Three questions and forty minutes on the first honest thing beats getting through all twenty.
When to use these and when not to
- Good with someone you already know well, on a long drive, a late night, or a walk where eye contact is optional.
- Not for a first date, a job interview, or anyone you have power over.
- Not while either of you is drunk enough that tomorrow will feel like a leak rather than a conversation.
- Not as a way to raise a grievance you have not named directly. If you already know what you want them to admit, say it instead.
- If they are currently in crisis, these become pressure rather than closeness. Ask what would help instead.
Common pitfalls
Collecting instead of listening
If you are already thinking about the next question while they answer, they will feel it and stop at the first safe stopping point.
Using the answer later
Anything raised in a future argument was not a conversation, it was research. One instance of this ends any chance of a second round.
Trading a deep answer for a shallow one
If they tell you something real and you respond with an anecdote, the asymmetry stings. Match what you were given before you ask for more.
Missing that something needs a different conversation
Some answers point at ongoing harm rather than history. When that happens, put the questions down and ask what they need, because continuing implies the answer was material.