Hypothetical Questions to Ask Your Parents
Twenty what-if questions about your family rather than their early lives, including a few that are hard to raise directly, such as what they would change about how they raised you and what they would want if they could not decide for themselves.
The questions
Open any question for the note
If you had to pick the age I was easiest to parent, which would you choose?
Why ask it
A light opener with a real answer behind it, because most parents have a clear favourite stage. What they liked about it usually says more about them than about you.
If you could go back to one trip or holiday we took as a family, which would you pick?
Why ask it
Shared memory is the easiest place to start, and the choice is rarely the expensive trip. Ask what they remember about the ordinary parts of it.
If our family could restart one tradition we let lapse, which would you bring back?
Why ask it
Practical as well as nostalgic, since you could actually reinstate it. Notice whether it stopped through drift or after a specific falling out.
If you had to describe our family to a stranger in three words, what would they be?
Why ask it
The three-word limit forces a choice rather than a description. Ask about the word you did not expect rather than the flattering ones.
If you could have one child-free weekend back from when we were small, what would you have done with it?
Why ask it
A gentle way to ask what they gave up, and easier to answer than a direct question about sacrifice. An answer about sleep is an honest one.
If you could keep only one photograph of me, which would you keep?
Why ask it
Easy to answer and specific, and the reason is usually about a period rather than a picture. Ask them to go and find it.
If you could pass on one thing you learned from your own parents, what would it be?
Why ask it
Connects three generations in one answer, and it separates what they inherited deliberately from what they repeated without noticing.
If you could undo one rule you set for me, which would you undo?
Why ask it
Smaller and safer than asking what they would change about their parenting overall, so it tends to get a genuine answer rather than a defence.
If you could change one thing about how you raised me, what would you change?
Why ask it
Ask it once, plainly, then stop talking. Many parents have an answer ready that they have never had permission to give, and filling the silence with reassurance wastes it.
If you had known how long the hardest stretch would last, what would you have done differently?
Why ask it
Lets them describe a difficult period without having to assign blame, and it often names a stretch you did not know was hard at the time.
If you could sit in on one week of my current life, which week would you want to see?
Why ask it
Shows what they are curious or anxious about, and it is much easier to answer than being asked outright what they worry about.
If you could stop worrying about one thing to do with me, what would you drop?
Why ask it
Most parents hold one worry back because raising it would sound like criticism. Naming it as a hypothetical lets it out without starting an argument.
If you could freeze our family exactly as it is now, would you?
Why ask it
A yes or no with a reason attached, and it tells you whether they think something is currently being lost or something is still on its way.
If you had to name the moment you stopped thinking of me as a child, when was it?
Why ask it
Usually a specific and surprising scene rather than an age, and it tells you what they think adulthood actually consists of.
If we had one long conversation left, what would you want it to be about?
Why ask it
Calm and open, and often the fastest route to whatever they have been meaning to say. If the answer is nothing in particular, take that at face value.
If you could decide now what the last years of your life look like, what would you want?
Why ask it
Asked away from any crisis, this gets their real preferences about where they live and who is nearby. Those are much harder to establish once something has happened.
If a doctor ever asked me to decide on your behalf, what would you want me to already know?
Why ask it
The hypothetical framing makes a necessary conversation possible. Write the answer down and tell your siblings, because this is the one you will be glad to have in writing.
If you could leave one thing behind for the family, what would you want it to be?
Why ask it
Answers about a letter, a recipe, a piece of land or a debt cleared are all things that can be acted on now rather than afterwards.
If you could hear one thing from me that you have never heard, what would it be?
Why ask it
Turns the question around, and it is the rare one where you can simply do what they ask straight away.
If you could be sure I remembered one thing about you, what would you want it to be?
Why ask it
A closing question that asks them to compress everything into something portable. Write down the phrasing before you lose it.
Talking to Your Parents About Family, Not Just History
Practical guidance for the conversation itself
How to ask them
- Use two light questions for every heavy one. The list is ordered that way for a reason.
- If both parents are present, be aware they will manage each other's answers. Some of these are worth asking one to one.
- Say why you are asking. 'I realised I do not actually know this' takes the suspicion out of an unusual question.
- Do not schedule this alongside a holiday or a birthday. Ordinary evenings produce better answers than occasions.
- When you get a real answer, stay with it. Following a good answer with the next question on a list is how people learn not to give them.
The four hardest questions here
What they would change about raising you
Expect a pause, and expect the answer to be smaller than you feared. Do not argue with it, and do not offer your own list in return unless they ask.
The worry they would drop
Whatever they name, resist fixing it in the same conversation. Being heard is the point; a plan can come later.
The last years of their life
Ask about preferences rather than logistics: who is nearby, what they would not want, where they would rather not be. Money and paperwork are a separate conversation.
Deciding on their behalf
Write down what they say and check whether it matches any document they have signed. If there is no document, this is the moment to ask whether there should be.
Afterwards
- Tell your siblings what you learned, particularly anything about care preferences or medical wishes.
- Write the exact words for the answers to the last few questions. Paraphrase loses the thing you wanted to keep.
- Do what they asked for on the question about hearing something from you. It costs nothing and it is the only one with an immediate answer.
- If a question landed badly, say so plainly next time you speak rather than avoiding the subject.
- Ask the same questions again in a year. The answers move, and the second version is often the honest one.
What goes wrong
Using a hypothetical to make a point
If you ask what they would change about raising you in order to get an apology, they will hear that immediately and the conversation is over.
Asking all four hard ones in one sitting
Back to back, they read as an agenda and put people on guard. Spread them across months if you can.
Treating a light answer as evidence
A favourite age or a photograph is not a verdict on anyone. Reading meaning into it teaches them to answer carefully.
Going quiet afterwards
If a parent says something difficult and you never mention it again, they will assume it was a mistake to tell you.