Unhinged Questions to Ask Your Boyfriend
Twenty absurd questions with enough of a premise to actually answer, ordered so the short silly ones come first and the ones that need a full committed bit come once he is warmed up.
The questions
Open any question for the note
You have to fight one animal every day for the rest of your life. Which animal do you pick?
Why ask it
The reliable opener, because everyone has an instinct and the instinct is always wrong. Whether he picks something small and endless or something large and occasional says more about his risk tolerance than any serious question would, and the follow up argument lasts twenty minutes.
Would you rather be permanently slightly damp, or permanently hear a faint kazoo?
Why ask it
Two mild horrors with no correct answer, which is the point. People who ask clarifying questions about the kazoo's volume before choosing are telling you exactly how they approach a decision at work.
You wake up as a kitchen appliance. Which one, and who in this house uses you first?
Why ask it
The second half rescues a tired question. Answering the appliance is nothing; answering who reaches for him and what for is where it gets funny and slightly pointed.
You're legally required to have a nemesis. Who is it and what did they do to you?
Why ask it
Gets the pettiest live grievance out of him under cover of a joke. What comes out is usually a real person from work or a neighbour with a leaf blower, and you will learn something you would not have got by asking what is annoying him.
What's the pettiest thing you've ever held a grudge about?
Why ask it
Follows the previous question naturally and confirms whether he was joking. Look for whether he can tell it against himself, because someone who cannot laugh at their own pettiness is only listing complaints.
You get one superpower, but it only works while you're standing in a supermarket. What do you take?
Why ask it
The constraint is what makes this better than asking about superpowers generally, because the obvious answers are useless and he has to actually think. The people who commit to something aggressively specific and local are the ones worth continuing with.
You have to be haunted. What should the ghost be obsessed with?
Why ask it
An invitation to build a bit rather than give an answer, and the first real test of whether he will play. If he gives you a one word answer, offer two absurd options and let him pick.
What's the weirdest thing you do when you're home alone that you'd deny under oath?
Why ask it
The under oath framing gives him permission by making it clear this is not going to be used as evidence. Go first with yours, because nobody offers this cold.
What's in your search history that you would defend in court?
Why ask it
Sharper than asking what he has searched, because it asks for the one he is proud of rather than the one he is embarrassed by. The best answers are long investigations into something completely pointless.
You can delete one food from existence. What goes, and who's going to be furious?
Why ask it
The second clause makes it social instead of a preference. If he names a food someone in his family loves, you get the family story attached to it, which is the actual payoff.
If a documentary crew followed you for a week, what would the episode be called?
Why ask it
Asks him to describe his own life from the outside, which is funnier and more revealing than describing it from the inside. A flattering title and a self mocking title are two very different answers.
You have to replace your name with a sound. What sound?
Why ask it
Nonsense with no possible correct answer, so the only thing being measured is whether he will make the sound out loud. He will need you to do yours first.
What's a conspiracy theory you don't believe but respect the craft of?
Why ask it
The phrasing lets him praise the construction without endorsing anything, which is the difference between this and a conversation you do not want to have. If he starts actually defending one, change the subject rather than arguing at eleven at night.
You have to fake your own death. What's the plan, and where do you turn up two years later?
Why ask it
A two part question that rewards elaboration, so it works best late when he is willing to build something. Where he chooses to reappear is a genuine answer about where he would rather be living.
You're in charge of a small country for one week. What's your first law?
Why ask it
The one week limit keeps the answers stupid rather than earnest, which is what you want here. If he goes serious and starts on tax policy, that is its own kind of information.
What's the dumbest hill you'd still die on tonight?
Why ask it
Distinct from the grudge question because this one is about an opinion rather than a person: the correct fridge layout, a film everyone else is wrong about. Expect to end up arguing it properly, which is the point.
If you had to give a forty minute talk with no notes, starting now, what's it on?
Why ask it
One of the most efficient questions here, because the honest answer is whatever he actually knows too much about. Then ask for the first three minutes of it and see whether he can do it, which he usually can.
You have to be reincarnated as an object in this room. Which one, and how long before you lose your mind?
Why ask it
Forces him to look around and pick something specific, which is harder and better than an abstract answer. The second clause is where the good detail is, because it makes him imagine the boredom rather than the object.
What's something you find genuinely funny that nobody else seems to?
Why ask it
The most honest question in the set dressed up as a silly one. Private humour that has never landed with anyone is a real thing to hand someone, and laughing at it properly is worth more than any of the answers above.
Which of these questions did you think was the stupidest, and what should I have asked instead?
Why ask it
Hands him the last word and usually produces a better question than the ones on this list. It also tells you whether he was enjoying it or being a good sport, which is useful to know before the next round.
How to Make Absurd Questions Land
Practical guidance for the conversation itself
How to Ask Them
Deliver it completely straight
The animal fight question is funny because it is asked as though it were a practical scheduling problem. Laughing before he answers tells him nothing is at stake, and he will match your effort level exactly.
Stay inside the premise
When he picks an animal, ask about the venue, the weather and whether he gets a weapon. Following up inside the joke is what turns a one line answer into the actual conversation, and stepping outside it to say that would never happen ends everything.
Give him multiple choice when he stalls
Some people cannot generate absurdity from nothing but are excellent at judging it. Offer two ridiculous options and he will usually reject both and produce a third, which is what you wanted.
Answer everything you ask
These only work as a trade. A round where one person asks twenty questions and answers none is an interview with a strange theme.
Do not explain what the answer means
Telling him his appliance choice reveals something about his childhood is the fastest way to end the game. Ask another question instead.
Two Runs That Build Well
The escalation
- 1Start with the animal you fight every day and let the argument about the weight class run all the way out.
- 2Move to the supermarket superpower, which needs the same kind of thinking but rewards more specific answers.
- 3Land on faking your own death, which is where someone who is warmed up will build a plan with a wig in it.
The petty run
- 1Open with the legally required nemesis, because it is nonsense with a real person hiding in it.
- 2Follow with the pettiest grudge, which will confirm the nemesis was not a joke at all.
- 3End on the dumb hill he would die on tonight, and then actually have the argument.
Ways This Falls Flat
- Asking three in a row without answering any yourself. It stops being a game around the second one and becomes a survey.
- Asking in a group when he is the only one being asked. Absurd answers need everyone equally exposed, or one person is just performing while the others watch.
- Over text, mostly. These depend on speed and on hearing him commit, and a good answer typed out and then reconsidered before sending loses everything.
- When he has had a bad day. Absurdity requires energy, and this list needs him to build things rather than agree to things.
- Reaching for the serious version underneath. There is a real question under most of these, and going after it directly halfway through is how a good evening turns into a different conversation neither of you planned.