Stupid Questions to Ask Your Friends
Deliberately silly questions for people who already know each other well. Mostly absurd hypotheticals and small confessions, with notes on which ones start an argument and which ones need a follow-up.
The questions
Open any question for the note
If you were a kitchen appliance, which one are you?
Why ask it
Almost everyone answers in two seconds, which makes it a good opener. The justification is the funny part, so ask why before moving on, and expect at least one person to argue about the toaster.
What's the weirdest thing you've ever eaten?
Why ask it
Reliably produces a story with a location and a witness attached. If someone answers in a single word, ask who made them eat it and the story appears.
What's the last thing you googled that you wouldn't want read out?
Why ask it
Most people paraphrase rather than read it, and the paraphrase is funnier than the original. Anyone who actually unlocks their phone has committed to the whole evening.
If you had to fight one animal with your bare hands, which one are you picking?
Why ask it
Splits a room instantly into people who choose something small and people who overestimate themselves. Someone will bring up geese and it will take ten minutes to recover.
What's something ridiculous you believed until embarrassingly recently?
Why ask it
Stronger than asking about childhood beliefs, because recently raises the stakes. There is usually one person who held onto something well into adulthood and has never told anyone.
If you could only communicate with one gesture for a week, what's the gesture?
Why ask it
Physical answers work well in a room because people demonstrate instead of explaining. Watch for whoever picks something useless and then commits to it for the rest of the night.
What's the most creative excuse you've used to get out of something?
Why ask it
Two answers in one: the excuse, and whether it worked. The failures are consistently the better stories, so ask how it went down.
If you were a villain, what's your evil plan?
Why ask it
Reveals more than people expect, because everyone's imaginary scheme maps neatly onto their real grievances. Petty plans get bigger laughs than world domination.
What's the strangest dream you can still remember?
Why ask it
Dreams are almost impossible to narrate well and that is half the entertainment. Interrupt with questions when the teller loses the thread, since they will be grateful.
If you could only eat one color of food forever, which color?
Why ask it
Turns into a genuine debate because everyone starts mentally inventorying their fridge. Beige is the answer that ends the argument and disappoints everybody.
What's the pettiest thing you've held a grudge about?
Why ask it
The smaller the grievance the better it lands, and people are usually delighted to finally be asked. Watch whether someone in the room turns out to be the grudge.
If you had to be famous for something embarrassing, what would you pick?
Why ask it
A safer version of asking about real embarrassments, so it works earlier in the evening and with people you know less well.
What's the weirdest thing you've done to avoid talking to someone?
Why ask it
Nearly everyone has hidden in a supermarket aisle. The location is what makes it funny, so ask where it happened and who they were avoiding.
If your day had a laugh track, when would it have gone off?
Why ask it
Forces a small recent moment rather than a polished anecdote, which usually makes it funnier and much easier for other people to match.
What's a skill you have that has never once been useful?
Why ask it
Where the genuinely strange talents come out, and about half the time someone can demonstrate theirs on the spot with a spoon or a coin.
If you had to wear one outfit for the rest of your life, what is it?
Why ask it
Separates the practical from the theatrical immediately, and somebody always tries to argue that a dressing gown is technically an outfit.
What's the worst nickname you've had, and who gave it to you?
Why ask it
The origin is the point. Nicknames from siblings are crueler and considerably better material than nicknames from friends.
If you could ask one object in this room a question, which object and what question?
Why ask it
Works because the answer has to use the actual room, so it never comes out the same way twice. Sofas and fridges tend to get accused of things.
What's the most confident you've ever been while being completely wrong?
Why ask it
The confidence is what makes the story, and people tell it on themselves surprisingly willingly. Expect at least one navigation disaster involving a motorway.
What would you do differently if you knew nobody would ever find out?
Why ask it
Sounds like another silly hypothetical and lands somewhere slightly more honest, which is why it belongs at the end of the night rather than the start.
How to use these questions
Practical guidance for the conversation itself
Running these at a table
Answer first yourself
Going first with a genuinely stupid answer sets the level. If you go first with a clever one, everybody else spends thirty seconds trying to be clever and the momentum dies.
Ask why, not what next
The laugh is almost never in the answer, it is in the reasoning behind it. One follow-up per question is worth more than four extra questions.
Let the arguments run
The one-color-of-food and fight-an-animal questions exist to start a fight nobody can win. Let that run for a few minutes and only then move on.
Which ones to use when
- Openers for a group that has just sat down: kitchen appliance, weirdest thing eaten, one gesture for a week.
- For a room that has gone quiet: fighting an animal, one color of food, the object in the room. All three produce cross-talk rather than turn-taking.
- For two or three people rather than a crowd: the petty grudge, the useless skill, the worst nickname.
- Late, once everyone is comfortable: the confident-and-wrong story and the last question. Both need trust to land as jokes rather than confessions.
Common pitfalls
Turning it into a quiz
Working down a list in order kills the room by the fourth question. Use three, follow the tangents, and drop the rest.
Aiming a question at one person
These work as invitations and fail as setups. If a question would only be funny at someone's expense, it is a joke about them rather than a question.
Pushing someone who passes
Anyone can skip. Move on without comment, because the fastest way to end the mood is to make an opt-out into a moment.
Ignoring who is in the room
Questions about grudges and being wrong land differently with in-laws, colleagues, or a new partner present. Save those for people who already have stories about you.