Fun Questions to Ask Your Dad
Twenty light questions about your dad when he was younger, for a drive, a barbecue or a quiet hour after dinner. Nothing here asks him to be serious, so it suits a conversation you want to be easy. If you want the harder subjects, the thirty question sitting is built for those, and the funny set is sillier than this one.
The questions
Open any question for the note
What did you and your friends get up to that would horrify you now as a parent?
Why ask it
Naming the double standard up front is what gets the real story, because he no longer has to defend the rules he set for you. This is also the safest possible opener, since nothing in it can be used against him.
What was your first car, and how did it end?
Why ask it
Every car has an ending and most of them are funny. Ask what it cost him and what he had to fix himself.
What did you spend your first proper paycheck on?
Why ask it
First money goes on something specific and slightly foolish, and men who deflect general questions about their youth will happily describe a car, a guitar or a stereo. Ask what happened to it.
What did your bedroom look like when you were fifteen?
Why ask it
Asking him to describe a room gets you posters, records, a shared bed with a brother, a window he climbed out of. Physical detail brings out stories that direct questions about his childhood do not.
What did you play loud enough that your parents complained?
Why ask it
Music is a fast way into his teens because he does not have to characterise himself, only name a band. If you can play it while he talks, the conversation runs longer than it otherwise would.
At eighteen, what did you think you'd be doing for a living?
Why ask it
The gap between the plan and the working life is where most of the interesting decisions sit. If he says he had no idea, ask who told him what to do instead, since somebody usually did.
What food from your childhood would you still eat today, and who made it?
Why ask it
This gets a grandparent or great grandparent into the room via something concrete. The dish is often plain and cheap, and the answer usually says something about how much money there was.
Which trip do you still think about?
Why ask it
Ask which one he thinks about rather than which was best, and you get the one with something unresolved in it. Some men name a trip they never took, which is a more revealing answer than a holiday.
What's the biggest risk you took, and would you take it again?
Why ask it
The second clause stops this becoming a triumph story. A father who says he would not do it again is telling you something about caution he has probably never said directly.
What did you get wrong that worked out anyway?
Why ask it
It gives him a way to admit a mistake without the confession, which is why it often gets a longer answer than a question about regret would. Listen for what he thinks was luck rather than judgement.
How did you know you wanted kids?
Why ask it
Many men of an older generation were never asked this and have no rehearsed answer, so what comes out is unusually honest, including if the honest answer is that he was not sure. Do not fill the silence for him.
What frightened you about becoming a father?
Why ask it
Fear is easier for most men to discuss retrospectively than in the present tense, and the answer is often about money or about repeating his own father. This is the question that changes how a lot of adults see their dad.
What was the first week with a newborn actually like?
Why ask it
Asking for the week rather than the moment gets past the hospital photo and into the exhaustion, the fear and the practical mess. It is also the story most likely to be new to you.
What did your own dad do that you decided not to repeat?
Why ask it
This surfaces the deliberate part of his parenting, the choices he made against something. Expect a pause; most people have thought about this for years without ever being asked.
And what did you copy without meaning to?
Why ask it
The follow up to the last question and the harder half, because it admits something outside his control. If he can name it, you have learned something about yourself as well.
What is the worst haircut you have had, and is there a photo?
Why ask it
Light, easy and almost always evidenced. It usually opens up the rest of the era.
What did you and your friends do at the weekend that cost nothing?
Why ask it
Free entertainment dates a decade precisely and the stories are cheerful. It is a good one for a long drive.
What was the best holiday you had before we came along?
Why ask it
Trips before children are remembered fondly and described in detail. Ask who else was there.
What is something you were briefly very good at?
Why ask it
Most fathers have a forgotten skill: a sport, an instrument, darts. Asking about it is a straightforward pleasure.
What do we do as a family now that you find funny?
Why ask it
It ends on the present and lets him say something affectionate without being asked to. Expect to be teased.
Getting a real conversation with your dad
Practical guidance for the conversation itself
Pick the setting carefully
- Side by side works better than across a table. Driving, fishing, walking, fixing something: many men talk far more freely when their hands are busy and nobody is watching their face.
- One question, then a long silence. The instinct to rescue the pause with a second question is what kills most of these conversations.
- Avoid the whole family being present. Answers given in front of your mother, your siblings or the grandchildren are edited for the room, and everybody knows it.
- Do not do this on a first attempt at a difficult relationship. Start with the first six questions, which are genuinely just fun, and see how it goes.
If you want to keep the answers
- 1Ask before you record, and put the phone on the table rather than hiding it. Most fathers say yes and then forget it is there.
- 2Choose four or five questions for one sitting rather than the whole list. An hour is plenty, and a second conversation is usually better than the first.
- 3Write down names, places, dates and wages as they come up. These are the details that get lost, and they are what your children will want.
- 4Ask the same question again years later if you can. The answer changes, and the change is worth having.
- 5If he is ill or his memory is going, start with questions eleven to sixteen. Childhood stories can be gathered from cousins; his account of becoming a father cannot.
When it does not go smoothly
He jokes instead of answering
Deflection with humour is a habit, not a refusal. Laugh, then ask the same question again in plainer words. If he deflects twice, drop it and come back another day; pushing a third time turns curiosity into interrogation.
The answer contradicts what you remember
Two people in one house had two different decades. Resist correcting him or adjusting your own account to match. Ask what it looked like from where he was standing, and keep your version for later.
Something painful comes up
A question about his father or about becoming a parent can land on a death, a divorce or a bad stretch you knew nothing about. Say plainly that you did not know, do not apologise at length, and let him decide how much more to say. The willingness to sit there without flinching is what makes him continue.
The relationship is strained
If you are barely in contact, this list is not a reconciliation plan. Pick two harmless questions, ask them by phone or in writing, and accept short answers. Anything that sounds like an audit of his parenting will end the conversation for another year.