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01 · Personal & Relational

Questions to Ask My Dad

Questions about the relationship rather than the life story. They are for an adult child who already knows the outline of their father's history and wants to talk about the two of you instead: what he saw during your childhood that you did not, what he thinks you got from him, what has gone unsaid, and what would make the time you have left together better. For his early years and his work, the general set covers that ground.

20 questions · each with a note on why · conversation guide

The questions

Open any question for the note

  1. What was I like as a small child, from where you were standing?

    Why ask it

    Your own memories start late and are patchy. His version of the first few years is the only record of them.

  2. What did you decide about me early on that turned out to be wrong?

    Why ask it

    Parents form impressions fast and rarely revise them out loud. This gives him a way to say that he was mistaken without it becoming an apology.

  3. What did you find hardest about me as a teenager?

    Why ask it

    Most fathers will answer this honestly if it is asked without heat. It usually explains a period both of you remember differently.

  4. Was there a time you were proud of me and did not say so?

    Why ask it

    Fathers of a certain generation have several of these. Asking directly is often the only way they get said.

  5. What do you think I get wrong about you?

    Why ask it

    It invites a correction, which is easier to give than a confession. Expect it to be about money, work or how much he noticed.

  6. What job did you hate, and what did it teach you?

    Why ask it

    The second half keeps this from being a complaint session. The worst job is usually where he learned whatever he has been trying to pass on to you in a less direct way.

  7. Was there a moment you decided what kind of father you wanted to be?

    Why ask it

    Some men have a specific scene for this and some have never thought of it as a decision at all. Either answer tells you something, and the ones who have a scene usually remember it clearly.

  8. What frightened you most when I was born?

    Why ask it

    Fear is easier for many fathers to discuss in the past tense than affection is in the present. Expect money, competence, or a fear of turning into his own father.

  9. Which of your habits do you see in me, and how do you feel about that?

    Why ask it

    The second half is the part that matters. Fathers often see inherited traits they are not pleased to have passed on.

  10. Was there a point when our relationship changed, and do you know why?

    Why ask it

    Leaving home, a row, a marriage, a death. Naming the moment is often the first step to talking about it properly.

  11. Which of your friendships lasted, and why do you think those ones did?

    Why ask it

    Men of his generation often lost most of their friends to distance and work without ever discussing it. The ones that survived reveal what he actually values in people.

  12. When did you stop feeling like you were pretending to be an adult?

    Why ask it

    The common answer is never, delivered as a joke, and it is worth taking seriously. It is also unusually reassuring if you are at the age of feeling like an impostor yourself.

  13. What is the closest call you have had?

    Why ask it

    A car, an illness, a night that could have gone differently. Fathers tend to keep these stories back from children on purpose, and hearing one changes how you understand a period of his life.

  14. What are you prouder of than anything in your working life?

    Why ask it

    Phrased to move him off the resume, since the honest answer is usually something small and domestic. If he names work anyway, ask what it cost at home.

  15. Is there anything between us you would like cleared up?

    Why ask it

    Direct, and easier to answer than it looks once the rest of the conversation has gone well. Leave it late in the day.

  16. What do you do with your days now that you actually enjoy?

    Why ask it

    Adult children often stop being curious about their father's present tense. If he cannot name much, sit with that rather than filling in an answer for him.

  17. What are you worried about now that you have not said out loud?

    Why ask it

    Health, money, and being a burden are the usual three, and none of them get raised unprompted. Ask gently, and be ready to just listen rather than solve it.

  18. What do you wish we did together that we do not?

    Why ask it

    This turns the conversation towards something you can act on. The answer is usually smaller and more achievable than you expect.

  19. What do you think I am like as an adult, honestly?

    Why ask it

    Fathers are frequently more admiring and more specific than their children expect. Ask for the honest version and then do not argue with any of it, or you will not get another.

  20. What would make the time we have better?

    Why ask it

    A plain closing question with no drama in it. Most answers are modest, a regular call or one visit a year without a crowd, and modest answers are the ones you can actually keep.

How to Have This Conversation

Practical guidance for the conversation itself

Setting it up

Two in a car beats twenty at a table

Many fathers talk more freely with a windscreen in front of them and no eye contact required. A drive, a task in the garage, or a walk works better than a declared sit-down.

One or two questions, not the list

Running through twenty questions turns it into an interview and he will start giving short answers. Ask one, follow it wherever it goes, and leave the rest for another visit.

Answer the same question yourself

Telling him what frightened you at your age, or what you got wrong, gives him permission and a level to match. Going first is the whole technique.

If you want to keep it

  • Ask before recording, and say plainly that it is for you and not for anywhere else
  • A phone on the table recording audio is less intrusive than a camera
  • Write down names, places, and years the same day, because those go first
  • Ask him to identify the people in two or three old photographs while you have him
  • If he says he would rather not be recorded, put the phone away and just listen

What derails it

Turning a question into an accusation

Asking what he got wrong while holding a grievance is not a question. If you need to raise something specific, raise it directly and separately, without the list.

Correcting his memory

He will remember dates and details differently from you and from your siblings. Ask what he remembers rather than establishing what happened.

Pushing when he closes down

A short answer or a change of subject is information. Let it stand, and return to that area months later rather than pressing the same afternoon.

Saving these for a crisis

If he is ill or frail, keep the questions few, keep them calm, and follow his energy. Better to ask the ordinary ones now, in a year when nothing is happening.