Deep Questions to Ask Your Sister
Twenty questions for sisters who talk often but not always about much. They cover what she thinks you have never noticed, what she took from watching your mother, the childhood you each remember differently, what she is not saying at the moment, and what she needs from you now.
The questions
Open any question for the note
What is the best thing happening in your life at the moment?
Why ask it
An easy opener that gets past the running commentary about work and family logistics. What she chooses first shows you where her attention actually is, which is often not where your conversations usually go.
What do you think I have never noticed about you?
Why ask it
Sisters assume they know each other completely, which is why the gaps go unexamined for decades. Expect something ordinary rather than dramatic, and expect it to be true.
Which of us do our parents find easier, and does it bother you?
Why ask it
Nearly every pair of sisters has a private answer and has never compared them. The second half is the useful part, because the ranking matters less than what she has done with it.
What did you copy from me, and what did you deliberately do differently?
Why ask it
Younger sisters in particular make a long series of decisions in reaction to an older one, usually without saying so. The deliberate differences are more revealing than the imitation.
What did you learn about being a woman from watching our mother?
Why ask it
You watched the same person and almost certainly took away different lessons about work, appearance and how much to accommodate other people. Comparing them explains a surprising amount about how you each live now.
What advice did you get growing up that you have since thrown out?
Why ask it
Families hand down rules about money, ambition and marriage that daughters quietly discard one at a time. Hearing which she dropped tells you what she has decided for herself rather than inherited.
What is something I do that you have never told me bothers you?
Why ask it
Sisters tolerate small irritations for decades rather than risk a row, so the list is long by adulthood. One item is enough, and the right response is thanks rather than an explanation.
Which part of our childhood do you think I remember wrong?
Why ask it
Two sisters rarely hold the same version, and the family usually settles on one and repeats it. The competing account often explains a resentment running underneath the agreed story.
What were you dealing with in your twenties that I missed?
Why ask it
There is normally a stretch where one sister was absorbed in her own life and simply was not looking. Naming the decade rather than the difficulty makes it easy for her to answer.
What is stalling the thing you most want to do?
Why ask it
More useful than asking about her dreams, because it asks about the obstacle rather than the ambition. Answers about money, timing and other people's needs are common and often solvable in part.
Who do you call before me?
Why ask it
Direct, slightly uncomfortable, and genuinely informative about where you sit. Whatever the name is, resist commenting on it and ask what that person does that you do not.
Where are you pretending to be fine at the moment?
Why ask it
Gives her a direct opening to drop the performance she keeps up with everyone else, including you. A general answer means it is not the moment, and a specific one means you should stop talking.
What did you learn from watching our parents that you are trying not to repeat?
Why ask it
You inherited the same patterns from the same house and have probably each flagged a different half of them. This is often the first time either of you has said any of it out loud.
What do you envy about my life, and what would you not want?
Why ask it
The second half is what makes the first half sayable. Comparison between sisters runs constantly and silently, and putting both sides of it on the table usually lowers the temperature rather than raising it.
What do you think I am getting wrong at the moment?
Why ask it
Most sisters are holding an opinion about your job, your partner or your health and have decided not to offer it. Asking once, on your own terms, is better than receiving it sideways for years.
What would you want me to do if you were in real trouble and could not tell me?
Why ask it
Worth agreeing before it is needed rather than improvising during a crisis. Answers often involve who else to call and what she would not want your parents told.
Is there anything between us that has never been settled?
Why ask it
Old incidents between sisters tend to be absorbed rather than resolved, and both parties usually know which one this is. If she names it, the repair matters more than establishing who was right.
What do you need more of from me, and what do you need less of?
Why ask it
Turns vague closeness into a request you can act on. The less of half is the one people skip, and it is the one worth waiting for.
What do you want this to look like when we are sixty?
Why ask it
Sister relationships are often held together by parents and holidays, and both eventually change. Naming what you each want early is how some sisters avoid the drift that follows a parent's death.
What do you hope I say about you?
Why ask it
Unusual and disarming, because siblings describe each other to other people constantly and never compare notes on it. What she names is effectively a request about how she wants to be understood.
How to Have These Conversations With Your Sister
Practical guidance for the conversation itself
Best Practices
Not in the Family House
Christmas, weddings and visits home put your parents in earshot and both of you back into childhood roles. A walk, a drive or a long phone call gets a different person on the other end.
Answer First
Go first on the harder questions, particularly the ones about envy and about what bothers her. A sister asked to volunteer a criticism from a standing start will usually decline rather than start something.
Do Not Defend the Family Version
When her account of an event contradicts yours, resist correcting it. The point of asking was to hear the other version, and arguing it back into shape guarantees you never hear another one.
Take the Criticism Without Explaining
If she names something you do that bothers her, say thank you and stop there. Explaining why you do it, however reasonably, teaches her that honesty costs her an argument.
Do Not Report It Onward
Anything she says about your parents, her marriage or her money stays with you. Sisters lose each other faster over repeated confidences than over disagreements.
Question Sequences That Work
An Easy Start
- 1What is the best thing happening in your life at the moment?
- 2What do you think I have never noticed about you?
- 3What did you copy from me, and what did you deliberately do differently?
- 4What advice did you get growing up that you have since thrown out?
Comparing Notes on Growing Up
- 1Which of us do our parents find easier, and does it bother you?
- 2Which part of our childhood do you think I remember wrong?
- 3What did you learn about being a woman from watching our mother?
- 4What did you learn from watching our parents that you are trying not to repeat?
When You Think Something Is Wrong
- 1What were you dealing with in your twenties that I missed?
- 2Where are you pretending to be fine at the moment?
- 3What would you want me to do if you were in real trouble and could not tell me?
- 4What do you need more of from me, and what do you need less of?
Worth Knowing Before You Ask
- Birth order changes what each of you was allowed to see. An eldest sister often knows about money trouble or illness that a younger one was protected from entirely.
- Step and half sisters have a different set of live questions, particularly about which household set the rules and who was treated as a guest.
- If there has been a long estrangement, start with the easy questions and leave the ones about unsettled business alone. They can wait for a second conversation.
- A sister in the middle of a crisis is not the audience for questions about old grievances. Ask what she is carrying and go no further.
- If she raises something serious about her health or safety, treat that as the conversation rather than one item on a list. Everything else can wait.
- Anything she says about your parents while they are still alive changes the family more if repeated than it changes you if kept.