Funny Questions to Ask Your Sister
42 light questions for sisters: the clothes that never came back, the phases she watched you go through, the times one of you covered for the other, and the family stories you each tell differently. Good for a long drive or a quiet evening at home.
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The questions
Each question, and why to ask it
What's the funniest thing I did as a kid that you still bring up?
Why ask it
She has a shortlist and probably a favorite, and she will tell it in the version she has been performing at family gatherings for years. Ask afterwards what she leaves out of that version.
What did you take from my closet and never give back?
Why ask it
Assumes it happened, which is what stops the automatic denial. Expect a specific item, and expect her to argue it was technically hers.
What's the weirdest thing about the house we grew up in?
Why ask it
Children assume their own house is normal. Comparing notes as adults usually turns up one room, rule or smell that neither of you questioned at the time.
What's the pettiest thing we ever fought about?
Why ask it
The stakes have to be gone for this to be funny. If she names something that still stings, take it seriously rather than laughing first.
What's the worst haircut either of us ever had?
Why ask it
Safe because it implicates both of you, and there is usually photographic evidence within reach. Ask who was responsible, since it is often a parent.
What's the most ridiculous thing you had to do to cover for me?
Why ask it
Two revelations for the price of one: what you did, and how much effort she put into hiding it. The second half is usually the surprise.
What's the funniest thing that has happened at one of our family holidays?
Why ask it
You were both there, so this becomes a joint retelling with disputed details. Whoever remembers the ending differently is usually the one who caused it.
Which of our relatives is reliably the funniest at a gathering?
Why ask it
Points the humor outside the two of you, which is a good reset if the last few answers got pointed. Expect immediate agreement on one name.
What's a photo of us you'd never let anyone see?
Why ask it
Everyone has one. Whether she will actually show it tells you how the evening is going better than any of her answers do.
What's the most embarrassing thing you've done in front of my friends?
Why ask it
Her memory of this and yours will not match, and often the moment she is mortified about is one you barely noticed. That gap is worth saying out loud.
What's a nickname you had for me that I never knew about?
Why ask it
Siblings run a private commentary for years. It is usually affectionate, occasionally not, and either way she has been sitting on it since you were both children.
What did our parents let us do that you'd never allow?
Why ask it
Works whether or not she has children of her own, because the answer is really about what looked normal then and looks alarming now.
What did you tell people about me when we were teenagers?
Why ask it
Depending on the age gap she was either your PR department or your opposition. The answer usually explains a reputation you never understood at the time.
What phase did I go through that you were secretly embarrassed by?
Why ask it
Secretly is what makes this land, since it invites something she never said at the time. Expect clothes, music or a friend group she wishes you had dropped sooner.
Which of my terrible ideas did you go along with anyway?
Why ask it
Implicates both of you at once, so nobody is alone in the story. These usually end with something broken and a parent given a very edited account.
What's the funniest argument you've had with our parents?
Why ask it
Moves the subject off the two of you for a round. Arguments retold years later are almost always about something absurdly small.
What family secret did you keep much longer than you should have?
Why ask it
Ambiguous on purpose, so she can answer with something trivial or something real. Follow whichever she chooses rather than steering it.
What's something I got credit for that was actually your idea?
Why ask it
A complaint she is finally allowed to make out loud. If she has an answer ready, it has been bothering her for a while, so let her have the moment.
What's something you got away with that our parents still don't know?
Why ask it
Needs a warm room and no parents in it. If she goes first, offer one of your own immediately, otherwise the confession sits there unbalanced.
What did you think about me back then that would surprise me now?
Why ask it
A good closing question because it can go warm or funny, and both are fine. Younger sisters often admit to admiration they would never have said at the time.
What did you talk me into as a kid that you still cannot believe worked?
Why ask it
This lets her confess and boast at the same time, which is the most reliable way to get a full story. Expect the method to be recognisable in how she asks you for favours now.
What did you get away with growing up that I took the blame for?
Why ask it
This is an old debt being settled out loud, and it usually gets paid because the statute has expired. If a genuine grudge surfaces, treat it as information rather than a punchline.
Who did our parents go easier on?
Why ask it
Almost every pair of sisters has an answer to this and has never compared notes. What usually emerges is that both of you thought it was the other, which is worth knowing before the next family argument.
What did you decide not to do because you watched me do it first?
Why ask it
Younger sisters run experiments on their older siblings whether or not anyone admits it. The answer often reveals that a choice you thought was private was being watched closely.
What did you keep hidden in your room?
Why ask it
Concrete and physical, so it is easy to answer, and it gets past the well worn family anecdotes. Diaries, letters, cigarettes, money: the object usually comes with a whole year attached.
What's the strangest thing you've found in my room or my bag?
Why ask it
Objects date the story precisely, which is why this produces better recall than asking about behaviour. Be ready for her to have kept it.
What was something of mine you were jealous of that I had no idea about?
Why ask it
Siblings misread each other's advantages in both directions, and this is where that surfaces. Answers are often about attention rather than objects, which is worth hearing properly.
What's a thing I do that you copied and never admitted?
Why ask it
Sisters borrow phrases, gestures and opinions constantly and rarely own up. Expect a pause first: the delay is her deciding whether to give you the real one.
Which of my friends did you actually like, and which did you not?
Why ask it
She watched them from the edge of the room with no obligation to be loyal. The dislikes are usually specific and, in hindsight, better judged than yours were at the time.
What's the first thing you'd do with a day as me?
Why ask it
The first thing named is usually something she thinks you are wasting, whether that is your free time, your job, or your wardrobe. Ask what she would refuse to do and you get the honest half.
Which of my habits would drive a flatmate up the wall inside a week?
Why ask it
Framing it around a hypothetical flatmate lets her be blunt without it being an accusation. She has lived with you, so the answer is evidence rather than opinion.
What do I do every time we're together that you've never pointed out?
Why ask it
Sisters clock the small physical patterns friends are too polite to name, and framing it around your time together keeps the answer current rather than about a teenager. Whatever she says will be accurate, minor and impossible to unsee afterwards.
What's something you've caught me doing when I thought I was alone?
Why ask it
This is teasing you have volunteered for, which is what makes it land as affection rather than a dig. If she trades one of her own back, the conversation is going well.
What food do I defend that you think is indefensible?
Why ask it
Food arguments are loud and cost nothing, so this is a good place to go after a heavier question. She will have a specific combination in mind and a witness.
What's the worst outfit I've ever left the house in?
Why ask it
There is almost certainly a photograph, so this turns into evidence rather than argument. Ask why she did not stop you, which is where the better story is.
What advice have you given me that you knew at the time I'd ignore?
Why ask it
This admits the pattern without either of you having to argue about who was right. Whatever she names twice is advice she still thinks you should take.
What do I do that reminds you of Mom?
Why ask it
Guaranteed to get a reaction, and the honest answers land somewhere between funny and uncomfortable. Ask for hers in return, or this stops being a conversation and becomes an assessment.
Which of us would last longer without a phone, and be honest?
Why ask it
A direct comparison gets a competitive answer, and the reasoning matters more than the verdict. Both of you will describe the other's habits more accurately than your own.
What's the funniest thing you've seen me do while trying to be serious?
Why ask it
This closes the set by letting her put you back in your place, which is the correct ending for a sibling conversation. Expect the story to be about a job interview, a speech, or a driving test.
What's the weirdest dream you've had about our family?
Why ask it
Nobody has to defend a dream, which is why this gets stranger material than a direct question about the family would. The relative who shows up in the dream is often the one on her mind.
If our family were a reality show, what would this season be about?
Why ask it
A season needs a plot, so this makes her name whatever the family is quietly circling right now. It is often the most accurate summary of the year you will hear.
What would you write on a plaque underneath a photo of me?
Why ask it
A plaque has to be permanent and short, so it pushes her past the easy jokes. What she writes is usually kinder than what she has been saying for the last ten minutes.
How to use these with your sister
Practical guidance for the conversation itself
Pick the moment
Two of you, not the whole family
Confessions about covering for each other and getting away with things need an audience of one. At a full family table she will give you the version that is safe for a parent to overhear.
Photographs help more than questions
An old album or a phone folder does half the work. Half these questions answer themselves once you are both looking at a picture from the year in question.
Answer everything yourself too
The closet question, the phases question and the credit question all put her in the position of accuser or accused. Taking your turn at each keeps it a conversation rather than a deposition.
Adjusting for the age gap
- If she is much older, she remembers years you do not. Ask what you were like before your own memory starts.
- If she is much younger, she watched your teenage years closely and formed opinions she never voiced. The nickname and phases questions are aimed there.
- If you are close in age, most stories are shared, so lean on the ones where your versions differ.
- With a large gap, skip the fought-about-what questions and ask instead what she assumed about you at the time.
- Twins and near-twins get the most out of the credit question, since attribution was probably a live issue for years.
Where these go wrong
Turning a memory into a scoreboard
Petty fights and disputed credit are funny until one of you starts counting. If either of you is tallying wins, put the questions down and change the subject.
Repeating her answers to a parent
The confession questions only work once. Anything she admits about getting away with something is not material for the next family dinner.
Laughing at a phase she is still sensitive about
Some phases were not funny at the time and are not funny now, particularly anything about how either of you looked. If her tone changes, drop it without commentary.