Questions to Ask Dad
The general set, for an ordinary conversation rather than an occasion. Twenty questions covering the house he grew up in, the jobs he took and hated, money, how he met your mother and what the first years of being a father were actually like. If you want the full life story in order, the thirty question sitting covers more ground, and there are narrower sets for the later years and for the two of you specifically.
The questions
Open any question for the note
Describe the house you grew up in. Who else was in it?
Why ask it
Asking him to describe a place gives him something concrete to start from, which is easier than being asked what his childhood was like. Rooms, who slept where and who was always there tend to bring out details that a general question never reaches.
What did your own father do for work, and did you understand it at the time?
Why ask it
Children rarely understand a parent's job, and the gap between what he knew then and knows now is where the interesting part sits. It also sets up a comparison he may make himself, about what you understood of his own work.
What were you like at sixteen? Would I have got on with you?
Why ask it
The second half changes the question from biography into something playful, and it often produces an admission he would not otherwise offer. Expect the answer to conflict with the version of him you grew up with, which is the point.
What was the first thing you bought with money you had earned?
Why ask it
A specific object anchors a whole period: the job, what he was paid, what things cost, who he was trying to impress. It is a light question that reliably produces a story rather than a sentence.
What job did you hate, and how long did you stay in it?
Why ask it
The length of time is the revealing part, because it tells you what he thought his options were and what he was carrying. Men of many generations were not asked about work they disliked, only about work they got, so this is often new ground.
When were you most short of money, and what did you do about it?
Why ask it
Families often have a period like this that was never explained to the children, and he may assume you already knew. His answer usually explains a house move, a car, a holiday that did not happen, or why he is careful in a particular way now.
How did you meet my mother, and what did you honestly think at first?
Why ask it
Asking for the first impression rather than the story gets you past the version told at anniversaries. Adapt it to your family: whoever the person was, the question works because first impressions are remembered with unusual precision.
What did you expect to be doing by forty that you never did?
Why ask it
This is the ambition question without the word ambition, and it is easier to answer than being asked about regrets. Some men have a specific answer they have never said aloud, and it usually explains something about how he pushed or did not push you.
What was the first year of being a father actually like?
Why ask it
The word actually gives permission for something other than joy, and fathers of older generations were rarely asked at all. Answers about fear, boredom or feeling peripheral are common and often a relief to say.
What did you think you were supposed to be like as a father?
Why ask it
Men often inherit a job description without noticing. Asking about the expectation rather than the performance makes it easier to answer honestly.
Was there a point when you thought you were getting it wrong with me?
Why ask it
This is a generous question rather than an accusation, and it lands better if you have already spent an hour on his own childhood. Whatever he names is worth listening to without correcting, even if you remember it differently.
What did you and my mother disagree about most when we were small?
Why ask it
Children absorb the tension without the subject, so this often fills in something you half remember. Keep it to the topic rather than to who was right, and expect him to be more diplomatic than accurate.
What was going on in our family that I was too young to notice?
Why ask it
There is usually something: a job loss, an illness, a relative in trouble, money that came from somewhere specific. Asking directly gives him a way to tell you now that the protecting is no longer necessary.
Is there a decision you made for us that you have never explained?
Why ask it
Moves, school changes and family rifts are the common ones, and the reasoning is often more considered than it looked from a child's height. If he cannot think of one, ask about a specific thing you remember not understanding.
Which friendships have lasted, and which did you let go of?
Why ask it
Men's friendships often thin out quietly in middle age, and the ones that survived say something about him that his work and family life do not. Ask what happened with a name you have not heard in years rather than pressing the general question.
Is there anything you have not told me because you thought I was too young?
Why ask it
Placed late, this is a straightforward invitation, and the answer may be nothing at all. If it is something, do not react to it in the moment beyond thanking him, because how you take the first disclosure determines whether there is a second.
What do you wish you had said to someone who is no longer here?
Why ask it
This is one of the few questions that reliably gets past a lifetime of understatement, and it is usually about his own father or a brother. Leave a long silence after asking, and be ready for the conversation to stop there for the day.
What do you worry about now?
Why ask it
Fathers routinely under-report this, and the honest answers are often about health, money outlasting them, or one particular family member. Whatever it is, resist the urge to solve it in the same conversation.
What has changed most about how families work since you were raising us?
Why ask it
This lets him compare rather than confess, which usually gets a longer answer. It often leads back to his own choices without you having to ask directly.
What do you know now that you wish you had known at thirty?
Why ask it
A broad closing question that suits an ordinary conversation. Most fathers answer it with something specific about work, money or patience.
How to use these questions
Practical guidance for the conversation itself
Setting it up
Do it side by side if he is not a talker
Many fathers say more in a car, on a walk, or while doing a job together than they do across a table. Sitting face to face with a list can feel like an interview, and the same question asked while driving often gets three times the answer.
Use photographs as prompts
An old picture does more work than any question, because it fixes a date and a place and brings up names. Go through a box of them and ask who each person was and what happened to them.
Take three questions per sitting
This is not a single conversation. Three questions answered properly, revisited over months, gets you far more than a long session that exhausts you both and covers everything shallowly.
Ask permission before recording
A voice recording preserves his phrasing and the way he tells a story, which is the part you will most want later. Ask first, keep the device out of the way, and offer to delete anything he would rather not keep.
While he is talking
- Leave silences. The most useful sentences usually arrive several seconds after you would normally have filled the gap.
- Do not correct his version of events, even when you remember it differently. You can hold both accounts, and arguing about the facts ends the story.
- Follow the names. Any person he mentions in passing is worth a question, and that is where the family history actually lives.
- Ask what he was doing rather than how he felt. Most men of older generations answer the first question and deflect the second, and the feeling comes through the detail anyway.
- Write down names, dates and places while you remember them. Recordings are hard to search, and the spelling of a great-grandmother's village is easy to lose.
Handling the harder ground
Accept a closed door the first time
If he changes the subject, let him. Returning to it in a month, once, is far more likely to work than pressing it now, and he will remember that you did not push.
Do not use the conversation to settle something
If you want an apology or an explanation for something specific between the two of you, that is a legitimate conversation and a separate one. Mixing it into questions about his life tends to end both.
Keep the practical question calm
Questions about papers, wishes and who to call are easier for everyone when they are asked in an ordinary week rather than in a hospital corridor. Ask once, take notes, and do not turn it into a longer discussion than he wants.
Notice if memory is the difficulty
If dates and sequences are slipping in a way that is new, adjust rather than test him: photographs, one topic at a time, and no questions that require him to reconstruct a chronology. If it concerns you, raise it with him and his doctor separately rather than during a conversation about his life.