Fucked Up Questions to Ask Your Friends
Twenty questions aimed at the group itself rather than at the past: who they would call from a police station, who they would not lend money to, what they have said about you when you were not there, and what they have stopped arguing with you about.
The questions
Open any question for the note
Who here would you call first from a police station?
Why ask it
A ranking question disguised as a joke, and the answers are rarely who people expect. What you learn is who the group thinks is competent under pressure, which is not the same as who they like most.
Who here would you not lend money to?
Why ask it
Uncomfortable but survivable, because everyone already knows the answer. It works best when the person named gets to explain themselves rather than just absorb it.
Which of us knows the most about you, and which of us knows the least?
Why ask it
It makes the closeness inside the group explicit, which groups usually avoid doing. The gap between how close someone thinks they are and where they land is where the honest conversation starts.
Who in this group have you been jealous of, and about what?
Why ask it
Naming the specific thing, a job, a relationship, a way of being at parties, keeps it from being an insult. Anyone who claims none has usually just chosen a different word for it.
What is the worst advice you ever took from someone in this room?
Why ask it
It gets at influence rather than affection, and the stories tend to be funny before they are pointed. The person who gave the advice almost never remembers giving it.
What is something you have thought about me and never said?
Why ask it
Asking on your own behalf is the only fair way to open this door, because you are taking the first hit. If nobody has anything, either you have easy friends or they do not trust the question yet.
What did you say about me when I was not in the room?
Why ask it
Almost everyone has said something, so the flat denials are the least believable answers of the night. The useful version is not the words but whether they would say them to your face now.
Which one of us would crack first under real pressure?
Why ask it
It sounds like a joke and functions as an assessment. Watch whether the group agrees on a name, since a unanimous answer nobody has ever voiced is a strange thing to discover.
Who here do you love but would never live with?
Why ask it
It separates affection from tolerance, which are easy to confuse in a group that mostly sees each other socially. The reasons are usually specific and mundane, which is what makes them land.
Have any of you covered for me without telling me?
Why ask it
It invites a small confession that is flattering rather than damaging, so people answer. Occasionally it turns up something you genuinely did not know, which is why it belongs here rather than early.
What decision of mine did you quietly disagree with?
Why ask it
Quietly is the word that opens it up, since it acknowledges they held back rather than accusing them of it. Expect a job, a move, or a relationship, and expect them to be at least partly right.
What do you think I am wrong about that you have stopped arguing with me on?
Why ask it
It surfaces the topics where the group has given up on you, which is a specific and useful kind of feedback. Anyone who names something you thought was settled is doing you a favour.
Whose relationship in this group worries you?
Why ask it
The most volatile question here and worth asking only in a group that can take it. If two people name the same couple, that is a conversation to have privately afterwards, not now.
What do we all pretend not to notice?
Why ask it
Groups run on shared blind spots: someone drinking too much, someone always broke, someone never invited to the same things. Asking as we rather than you shares the responsibility for it.
If one of us needed to hear a hard truth tonight, who and what?
Why ask it
It makes people choose whether to actually say the thing, which is a real test of the friendship. The person naming has to be willing to stay in the room afterwards.
Who would you want beside you if you got bad news, and who would you not?
Why ask it
The second half is what makes it honest, and the answers are about temperament rather than loyalty. Being the person nobody wants in a crisis is worth knowing, and it is fixable.
What do you think I would say about you right now?
Why ask it
It reveals what people assume you think of them, which is usually harsher than the truth. Correcting a wrong guess out loud is the most useful thing that happens in this whole list.
What would make you walk away from this group?
Why ask it
Friendships are usually treated as permanent until they are not. Naming the actual line, disloyalty, a partner, being consistently left out, means the group knows where it is.
What would our friendship look like if we met for the first time today?
Why ask it
It quietly asks whether the group is chosen or inherited, and the honest answers can sting. It is also the most likely question here to produce something worth acting on.
What would you want me to say to you honestly, right now?
Why ask it
The best closer because it hands over the last word and turns the evening from criticism into something mutual. Whatever they ask for, they get to hear it, which is the whole agreement.
Turning questions on the group itself
Practical guidance for the conversation itself
How to do this without wrecking the night
Ask about yourself first
These questions are aimed inside the group, which means somebody is always the subject. Volunteering to be the subject first makes it an agreement rather than an ambush, and it changes what people are willing to say.
Set the no-consequences rule out loud
Nothing said tonight gets used in a future argument, and anyone can pass. Say it before the first question, because saying it after the first sharp answer sounds like damage control.
Keep the group even
If one person answers everything and one person answers nothing, the night stops being shared and starts being about them. Take questions in the same order every round.
Finish on the last question
Ending on what would you want me to say honestly gives everyone something to leave with. A night of this that ends on the hardest question tends to sit badly for weeks.
Before you start
- This needs a group with real history. Newer friendships do not have the credit to absorb it.
- Any live conflict between two people in the room will hijack every question, so resolve it or wait.
- Do not run this with partners present unless the partners are also part of the group.
- Keep the drinking moderate. Honesty from someone who is drunk arrives as bluntness and reads as contempt.
- Agree in advance that anything about a relationship or someone's drinking gets picked up privately afterwards rather than debated at the table.
Common pitfalls
Using a question to land a grievance
If you already know what you want said about someone, you are not asking, you are staging. Have that conversation with them directly and leave the group out of it.
Piling on once someone is named
The moment two people agree on a target, the third joins in and it stops being honest. One answer, one reply from the person named, then move on.
Punishing the honest answer
Someone tells you what they really think and gets frozen out for a week. That is the end of the group being honest about anything, and it is entirely on the person who asked.
Playing this when someone is on the outside
If one person is already the group's current problem, every question turns into a referendum on them. Wait until that is resolved, or do not play.