Questions to Ask an Older Woman
Questions for getting to know an older woman as a person rather than a source of advice: what she is doing now, what she had to fight for, what she has stopped putting up with, and what nobody ever asks her about.
The questions
Open any question for the note
What are you working on or looking after at the moment?
Why ask it
Opening in the present avoids the assumption that her interesting years are behind her, which is the mistake most of these conversations start with. The answer is often a project, a garden, a committee or another person, and any of them gives you somewhere to go next.
Did you train for what you ended up doing, or fall into it?
Why ask it
For many women the answer involves a path that was closed, a course that was not available or a job that had to be left on marriage or pregnancy. It gets at her working life without making her summarise a career.
Who were you at twenty five, and would she recognise you now?
Why ask it
More interesting than asking what she has learned, because it asks for a comparison rather than a lesson. Expect the answer to be about confidence or about how little of her own opinion she used to voice.
What did you teach yourself because nobody would show you?
Why ask it
Plumbing, accounts, driving, a trade, a language: there is usually something learned in the face of an assumption that she could not. This is where competence gets described plainly, which she may not have been invited to do in years.
What did you want that you were not supposed to want?
Why ask it
A careful question that opens up ambition, independence, a different life or simply time alone. Ask it once, leave room, and do not push if she moves past it.
Which of your friendships has lasted longest, and what holds it together?
Why ask it
Long friendships between women often carry the practical history of each other's lives, including things no family member knows. Ask what has been forgiven, which is usually where the real answer sits.
What are you better at now than you have ever been?
Why ask it
Most questions aimed at older women assume decline, and this one assumes the opposite, which tends to get a genuine laugh and then a serious answer. Follow up by asking when she noticed.
What did you have to fight for that people now assume was easy?
Why ask it
Depending on her age and where she lived, that could be a mortgage in her own name, a bank account, a place on a course or being taken seriously in a meeting. Listen without treating it as history, since much of it was recent.
Whose expectations were you carrying, and when did you put them down?
Why ask it
Usually a mother, a husband, a church or a workplace, and the moment of putting them down is often specific and rememberable. If the answer is that she has not, that is worth hearing without a suggestion attached.
What did having children, or not having them, turn out to mean for your life?
Why ask it
Phrased to work either way, which matters because the assumption that every older woman is a mother is common and stings. Whatever she says, do not respond with sympathy she has not asked for.
What are you reading or listening to that would surprise people?
Why ask it
It puts you on equal footing and it reliably breaks whatever assumption you arrived with about her taste. It is also the easiest of these questions to return to next time you meet.
Where do you go when you want to be by yourself?
Why ask it
Women who have spent decades being available to a household often have a very precise answer, and it is rarely a room of their own. The specificity of the place tells you how hard-won it is.
What do people misjudge about you when they first meet you?
Why ask it
Direct, easy to answer, and it usually names something she has been quietly correcting for a long time: being read as timid, as unqualified, as somebody's wife. It also tells you what not to do for the rest of the conversation.
What do you no longer put up with?
Why ask it
Reliably the most enjoyable question in this list to ask, and the answers are specific rather than philosophical. Ask what happened the first time she said no, which is usually the story underneath it.
Who taught you the most, and did they ever know it?
Why ask it
Often a teacher, an aunt or a colleague rather than a parent, and often someone who never found out. The unspoken gratitude is the part worth asking about.
What is the bravest thing you have done that nobody applauded?
Why ask it
Leaving, staying, telling the truth to family, taking on a debt, raising a child alone: courage in most lives is unwitnessed. Naming it aloud is the point of the question.
What has aged badly about the advice you were given?
Why ask it
This lets her be critical rather than sage, which is a relief if she is tired of being cast as a source of wisdom. Expect something about marriage, appearance, money or keeping the peace.
What do you want to do next?
Why ask it
Asked plainly and taken seriously, this treats her as someone with a future, which older women are routinely denied. If part of the answer needs a lift, a companion or a form filled in, that is something you can act on.
What would you want a younger woman to hear from you that is not advice?
Why ask it
Ruling out advice is what makes this different from every question she has already been asked a hundred times. You usually get an observation, a warning or a piece of solidarity instead of a maxim.
What would you like to be asked about that people never ask?
Why ask it
Ask it last. The answer often reveals a whole part of her life, a job, a talent, a person, that has gone unmentioned because everyone assumed the interesting subject was her children or her health.
Conversations That Do Not Condescend
Practical guidance for the conversation itself
How to Come Across
Do Not Make Her Age the Subject
Telling a woman she looks good for her age, or is remarkable for still doing something, lands as an insult with a compliment wrapped round it. Talk about what she is doing, not how surprising it is that she is doing it.
Ask About Work and Money, Not Only Family
Women in older cohorts are habitually asked about husbands, children and grandchildren and rarely about their own trade, wages, training or ambition. The unasked half is usually where the better conversation is.
Do Not Cast Her as a Wisdom Dispenser
Constantly asking for life lessons is flattering for ten minutes and tiring after that, and it puts her in a role rather than a conversation. Mix in questions with ordinary answers.
Let Her Finish
Interrupting and completing sentences is the most common way this conversation goes wrong, and it is often habitual rather than deliberate. Count to three before you speak.
If You Are Hoping She Will Mentor You
- Ask a specific question rather than for her time in general, since a defined ask is far easier to say yes to
- Do your reading first; asking what she has already published or told you is a poor use of goodwill
- Be clear about what you want, whether that is an introduction, a judgment on a decision or an honest read on your work
- Say what you did with her last piece of advice before asking for the next one
- Do not expect free labour dressed as mentorship, especially review of long documents
- Ask what would be useful to her, and mean it
- Keep to the time you asked for and end the conversation yourself
If This Is a Date
- Do not make the age gap the running theme; if it needs discussing, do it once and plainly
- Skip the comparisons with women your own age, which flatter nobody
- Ask about her life as it is now, not what she can teach you
- Assume she has a full existence with commitments and friendships that do not revolve around you
- Ask what she wants from this rather than deciding it is casual on her behalf
- Do not ask about her children or her divorce in the first hour
- Take a no as final the first time it is said