Deep Questions to Ask Your Parents
34 questions for anyone who wants to know their parents as they are now and as they were. They cover what fills their days, what they were like at your age, what they carried without telling you, money, faith, forgiveness, health, and the practical arrangements nobody wants to raise first.
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The questions
Each question, and why to ask it
What are you enjoying at the moment that we never talk about?
Why ask it
Adult children mostly ask about health and logistics, so a parent's current interests go unmentioned for years. An easy opener that often reveals a hobby, a friendship or a project you knew nothing about.
What do your days actually look like now?
Why ask it
The shape of a week after children and often after work is invisible from a distance. Whether they describe structure or emptiness is worth knowing, and it is a kinder route into loneliness than asking directly.
What do we never talk about that you wish we did?
Why ask it
Hands them the agenda rather than making them wait for the right question. Many parents name something small they assumed you were not interested in, which is easy to correct once said.
What did you make of me when I was a teenager?
Why ask it
Parents rarely report this honestly at the time, so the real assessment has never been given. Expect it to be both more worried and more admiring than the version you grew up hearing.
What are you proud of that has nothing to do with us?
Why ask it
The qualifier is what makes this useful, since the reflex answer for most parents is their children. What they name instead, work, a friendship, something they endured, is usually never mentioned.
When did you last feel out of your depth?
Why ask it
Adults tend to assume their parents stopped being uncertain, and hearing about something recent corrects that fast. Technology, medical appointments and money commonly feature.
What are you afraid of these days?
Why ask it
The present tense matters, because fears change with age and the current one is rarely the one you would guess. Answers about being a burden come up often and deserve a straight response rather than reassurance.
What were you carrying through those years that you never told us about?
Why ask it
Illness, debt, job insecurity and difficulty in their relationship are routinely hidden from children and never revisited afterwards. The answer often reorganises a period you remember only as an atmosphere.
Are you comfortable with money now, honestly?
Why ask it
Parents understate this consistently, particularly to children they think are stretched themselves. Asking plainly is more useful than asking whether they need anything, which is easy to decline.
Has what you believe about God changed over your life?
Why ask it
Asking about change rather than belief avoids a defence of a position and gets you the actual history. Many parents have moved a long way from the faith they raised you in and have never said so.
Is there anyone you have not forgiven?
Why ask it
Long family silences usually rest on one unrepaired incident that the next generation cannot name. Their answer may explain a relative who was never at Christmas.
Is there anyone who has not forgiven you?
Why ask it
The harder half of the pair, and the one that requires them to take a share of it. A parent willing to answer this is telling you something about how they see their own conduct.
What advice do you bite your tongue on?
Why ask it
Most parents of adult children are holding back an opinion about work, money or a partner. Inviting it once, on your own terms, is better than receiving it sideways for years.
What do you wish I would ask you for help with?
Why ask it
Being useful matters to parents long after their children stop needing them, and most will not volunteer it. The answer is often practical and easy to grant.
What are you dreading?
Why ask it
Short and unusually direct, which is why it works. Answers tend to be concrete: a procedure, a birthday, outliving someone, a house that has become too much.
How do you feel about getting older?
Why ask it
Worth asking calmly and without steering toward the positive. Listen for whether the difficulty they describe is physical, social, or about no longer being consulted.
Is there anything about your health you have not told us?
Why ask it
Parents commonly downplay diagnoses and appointments to avoid worrying their children. Asking plainly, once, is what makes it possible for them to say it, and it should not be followed by questioning.
If something happened to you, who should we call, and where is everything kept?
Why ask it
Best asked while it is entirely hypothetical and nothing has to be decided. Names, documents and account details are the things families spend weeks searching for at the worst possible time.
What do you want to do while you still can?
Why ask it
Practical rather than sentimental, and often answered with something modest: a place, a person to visit, a task finished. It is the one question on the list that can be acted on immediately.
What do you want us to remember about how you lived?
Why ask it
Most parents have thought about this and have never been asked. What they name is usually a request about how to treat other people rather than anything about themselves.
What do you remember about the day I was born?
Why ask it
An easy opener that almost always produces detail nobody has told you: the weather, the drive, who was in the room, what went wrong. It also sets the tone that you are asking for their memory rather than their advice.
What do you remember about deciding to have children?
Why ask it
Some parents describe a plan and some describe events that happened to them, and which one you get is worth knowing. The answer often includes a hesitation nobody has mentioned to you before.
What were you like at my age?
Why ask it
Naming your own age makes the comparison concrete and often stops them narrating a general past. Expect the answer to reframe something about your childhood, because most people were less settled at your age than their children assume.
What did you think your life was going to look like, and how close did it get?
Why ask it
This gets at the plan behind the life rather than the life itself. Whether they treat the gap between the two as a loss or as a relief tells you more about them than any question about regret.
What did you give up in order to raise us?
Why ask it
Asking directly gives permission for an answer they would never volunteer, since most parents believe naming the cost sounds like blaming the children. A parent who insists they gave up nothing is usually protecting you.
When was money tightest, and did we know?
Why ask it
The second half is the point. Many parents worked hard to make sure their children never noticed, and hearing what was going on behind an ordinary year is one of the more affecting things they can tell you.
What was the hardest year of your life?
Why ask it
Naming a single year is far more answerable than naming a hardest thing, and the year they choose is often not the one you would have guessed. Frequently it is a year you lived through without noticing anything was wrong.
Is there a decision you still turn over?
Why ask it
This is gentler than asking about regret and tends to get a truer answer, because it asks what is still live rather than what they would undo. Listen for whether the decision involved you.
What did your parents get right, and what did you decide not to repeat?
Why ask it
Most parenting is a deliberate correction of the previous generation, and the specific thing they refused to repeat explains a rule you grew up with. It also puts your grandparents in the room.
What do you wish you had asked your own parents?
Why ask it
This is usually the question that makes the whole conversation click, because it puts them on your side of the table. Whatever they name is the thing you should be asking them next.
Who in the family do I remind you of?
Why ask it
The comparison is usually to someone you barely knew or never met, which opens a door into people who exist only as photographs. It also reveals what they quietly watch for in you.
Who did you lose that you still miss?
Why ask it
Grief that is decades old rarely comes up at family gatherings and is often still close to the surface. Expect a name you have heard mentioned only in passing, and let the pause after it run.
What do you think we get wrong about you?
Why ask it
This hands them the chance to correct the family story, which is normally fixed by the time children are adults. The correction is often small and specific, and it lands harder than a general reflection.
What would you want us to do if you could no longer manage on your own?
Why ask it
Better asked long before it is needed, when nobody is under pressure and nothing has to be decided. Concrete answers about housing, care and who they would want making decisions are worth writing down.
How to Have These Conversations With Your Parents
Practical guidance for the conversation itself
Best Practices
Ask Alongside a Task
Driving, walking, cooking or clearing out a cupboard produces more than a conversation that has been scheduled. Parents who go quiet when told there is something to discuss will talk freely over a job.
Ask Each of Them Separately at Least Once
Parents manage each other's version of events when both are present, particularly about money and the years they were raising you. One conversation alone gets a different account.
Raise the Practical Questions Early and Once
Health, documents and who to call land best while they are hypothetical. Bringing them up during a crisis makes them sound like a negotiation about control.
Do Not Argue With How They Feel About Age
Contradicting a parent who says they feel less useful, or telling them they look well, is a way of declining the subject. Ask what would help instead.
Accept One Deflection
A parent who moves past the same question twice is refusing it, and pressing costs you the rest of the conversation. Return to it in a few months rather than a few minutes.
Question Sequences That Work
An Easy Start
- 1What are you enjoying at the moment that we never talk about?
- 2What do your days actually look like now?
- 3What are you proud of that has nothing to do with us?
- 4What do we never talk about that you wish we did?
The Years You Lived Through Together
- 1What did you make of me when I was a teenager?
- 2What were you carrying through those years that you never told us about?
- 3Is there anyone you have not forgiven?
- 4Is there anyone who has not forgiven you?
The Practical Conversation
- 1Are you comfortable with money now, honestly?
- 2Is there anything about your health you have not told us?
- 3If something happened to you, who should we call, and where is everything kept?
- 4What do you want to do while you still can?
Worth Knowing Before You Ask
- Wishes about care, money and medical treatment carry no legal weight unless they are documented. If their answers are clear, ask whether anything has been written down and where it is kept.
- Siblings should hear the practical answers directly rather than secondhand. Raising it once with everyone present prevents a later disagreement about what was said.
- If a parent describes a symptom or a diagnosis you were not told about, the useful next step is asking to come to the next appointment rather than researching it for them.
- Financial questions can read as an interest in inheritance. Saying plainly why you are asking removes most of that risk.
- A parent living alone after a bereavement may answer the questions about their days very differently a year later. It is worth asking more than once.
- If your relationship is difficult, the questions about their current life are far safer than the ones about your childhood. Those can wait indefinitely.