350+ Intriguing Questions to Ask Your Dad

Andrew Ronald

Simirity Founder | Father of two

17th October, 2025

How well do you really know your dad? These questions to ask your dad will guide you towards engaging conversations that uncover the stories he’s never thought to share. 

I was fortunate to have a dad who’s always been ready to share stories from his past. The problem was with me—I never knew what to ask. When we’re young, the world revolves around us. When we become parents, it revolves around our children. It’s only now, in my late 40s with teenage children, that I’ve realised how much about his life I don’t know. Thankfully, I didn’t wait too long, and asking the right questions has revealed a whole world of untold stories and life lessons that shaped not just his life, but mine too. 

Identifying the right questions to ask your dad is an essential first step, and we’ve created the ultimate collection of guides to help.

Choose your approach to uncovering your dad’s story

Not all dads communicate the same way.

Some open up naturally in conversation. Others find it easier to reflect and write when they have time to gather their thoughts. Your dad might be comfortable with emotional discussions, or he might express himself better through stories about what he did rather than how he felt. 

We can help with both approaches:

1. Memory book templates — Foundational questions your dad can complete independently, creating a tangible keepsake (free Word document downloads)
2. Guided conversations — 350+ questions organized into 13 themed discussions that unlock your dad’s deepest stories through natural dialogue (free PDF download)

Right now, your dad carries decades of experience, hard-won lessons, and family stories that exist nowhere else. Not in documents. Not in photos. Only in his memory.

Asking your dad questions about his past isn’t just about satisfying your curiosity… It’s about preserving his stories. It’s about deepening your connection with him while you still can. It’s about giving your children and grandchildren the gift of really knowing who their grandfather was.

Jump to section:

• Memory Book for Dad vs Guided Conversations
• 13 Themed Conversations With 350+ Simple Questions to Ask Your Dad
• Conversation 1 – Childhood Years and Family History
• Conversation 2 – Family and Friends
• Conversation 3 – The Early Years of Their Relationship
• Conversation 4 – His Parenting Journey
• Conversation 5 – Your Childhood Through His Eyes
• Practical Questions to Ask Your Dad
• 30 Must-Ask Follow-up Questions
• Free Download: All Interview Questions to Ask Your Dad
• BONUS – 7 Tips for Asking Your Dad Questions
• 3 Reasons to Have These Conversations Soon
• FAQs About Asking Your Dad Meaningful Questions
• Other Ways to Bond With Your Dad

Memory Book for Dad vs Guided Conversations

Start with a memory book: The foundational approach

The simplest way to begin capturing your dad’s stories is through a memory book or keepsake journal—a curated collection of foundational questions covering all phases of life that he completes at his own pace.

Why memory books are a great starting point:

• Hands-off simplicity — Give him the book and he takes it from there.
• Independent completion — Your dad works through it on his own timeline.
• Time to reflect — He can think deeply about his answers before writing.
• Tangible heirloom — A physical keepsake to pass down through generations.
• Essential facts covered — Birthplace, education, career, and major life events.

You can download our free memory books (Essential: 25 questions, Complete: 65 questions) or purchase a physical version like this one.

Why conversations reveal what writing can’t

Memory books are limiting in their design. You read the question, fill in the blank, and move to the next. They capture what your dad thinks you want to know. 

• Written question: “What were your teenage years like?” 
• Written answer: “Pretty typical for the 60s. Went to school, had a few close friends I used to meet with and worked part-time at the local shop.”

But you were probably hoping for something more…

Standardised memory book questions lead to disappointing answers—and the stories that you actually want to know about are rarely shared.

In a conversation, “What were your teenage years like?” may have a similar response at first, but the difference is you get to ask questions to dig into the details. In doing so, you find out what was ‘typical for the 60s’, what school was like back then and what he used to get up to with this friends.

In this way, you uncover questions that you never thought to ask and hear stories that your dad never thought to share.

When I wanted to explore my own father’s story more deeply, I searched for conversation guides to get me started, but found none. The hundreds of questions scattered across the internet had no logical flow, and the sheer number made it quite intimidating to start. So I collected the best questions, added many new ones, and organised them into 13 themed conversations you can have with your dad.

I’ve tested these guides with my own father, and those conversations were without doubt the most precious we’ve ever had—exploring parts of his life and personality I’m ashamed to have overlooked for so long.

Why guided conversations are so much more valuable:

• Depth and authenticity — Your dad’s stories become spontaneous and genuine when shared in real-time dialogue, not constrained by pre-written answers.
• 350+ questions vs 100 — Our conversation guide contains many more questions than typical memory books, exploring topics most books never touch.
• Natural discovery — You can ask follow-up questions immediately, uncovering stories he’d never think to include in a written response.
• Emotional connection — Conversations naturally deepen your bond in ways writing alone cannot.
• Unexpected revelations — The natural tangents and detours often lead to the most meaningful discoveries about who your father really is.

One potential downside: Unlike a written book, conversational stories can be forgotten if you don’t record them somehow. We recommend recording your conversations, and later we’ll show you how you can share these recordings alongside photos, videos, and other family media.

Which approach is right for you?

Many families use both! Start with a memory book to capture foundational facts, then use our conversation guides to explore the stories behind those facts. The memory book gives you the outline of your dad’s life; the conversations fill in the details and add the personal touch.

Capture your family’s history before it’s too late.

SIMIRITY JOURNAL

13 Themed Conversations With 350+ Simple Questions to Ask Your Dad

Organising questions by themes helps create a more focused and enjoyable conversation. It allows you to explore one area of your dad’s life at a time, making the discussion feel more natural and less overwhelming.

So what should you do next?

1. Find a theme from below that interests you.
2. Identify the questions you want to ask (you can print the PDF guide and highlight them).
3. Prepare the environment for questioning.

Based on my family’s experience, I would recommend allowing at least one hour, ideally two, for each of the following conversations.

1. Childhood and Family History (included below)
2. Family and Friends (included below)
3. Early Relationship Years (included below)
4. His Parenthood Journey (included below)
5. Your Childhood Years (included below)
6. Life-long Learning (only in PDF)
7. Career (only in PDF)
8. Hobbies and Interests (only in PDF)
9. Travel and Places (only in PDF)
10. Challenges and Milestones (only in PDF)
11. Witnessing Historical Changes (only in PDF)
12. Reflections on Life (only in PDF)
13. Retirement and the Future (only in PDF)

Conversation 1 – Childhood Years and Family History

Discover the stories that shaped your dad’s early years and family background. These questions to ask your dad will help you uncover meaningful memories and insights about his childhood and upbringing.

1. Family origins

1. Where did you grow up, and what was it like living there?
2. Did your family ever move, and how did that affect you?

2. First memories

3. What is your earliest memory?
4. Who were the most important people in your life when you were young?
5. What are some of your fondest memories of places you visited as a child?
6. What is your favourite memory with your parents?
7. Were there any sounds, smells, or sights that remind you of your childhood home?

3. Early life

8. What comes to mind when you think about life before starting school?
9. What was your favourite toy or activity growing up?
10. What childhood holiday memories stand out to you the most?
11. How would your parents or siblings describe you as a child?
12. Did you have a favourite teacher or subject in school, and why?
13. Did you ever have a nickname growing up? How did you get it?
14. Did you have any special talents or skills that stood out during your childhood?

4. Teenage years

15. Can you remember a time you got into trouble as a teenager? What happened?
16. What was a typical evening like for you as a teen?
17. What did weekends usually look like during your teenage years?
18. What kind of chores or responsibilities did you have as a teenager?
19. What were some of the popular trends, music, or fashion during that time?
20. Did you have any close friends as a teenager? What did you do together?
21. Did you ever rebel against your parents? How did they respond?
22. What was your first part-time job, and what was it like?

5. Becoming independent

23. What was it like moving away from home for the first time?
24. How did you feel when you started living on your own?
25. What life lessons did you learn during this time?
26. How did your relationship with your parents change after you left home?
27. Was there a moment when you felt like you had truly become independent?

6. Traditions and customs

28. What were the most important family traditions or rituals?
29. How did your family usually celebrate birthdays, holidays, or other milestones?
30. What foods were often served at family occasions?
31. Were there any annual trips, events, or gatherings that you looked forward to?
32. What religious practices or customs were a part of your upbringing?
33. Can you share a memory of a special family gathering or celebration?
34. How did your family create a sense of togetherness or belonging?
35. Are there traditions you carried forward into your own family?

Your family’s past, present & future—woven together in Simirity.

SEE HOW

Conversation 2 – Family and Friends

Family and friends are the cornerstones of life. These questions to ask your dad uncover the connections, relationships, and stories that shaped his world, offering you a deeper understanding of the people who influenced him most.

Your dad’s parents

1. Where were your parents born, and what were they like?
2. How would you describe their approach to life?
3. What do you remember most about your mom and dad?
4. What were the most important values to each of them?
5. Can you share anything about their backgrounds or careers?
6. How did they meet and decide to get married?
7. How would you describe their parenting style?
8. If they could leave a message for their great-grandchildren, what do you think it would be?
9. What might their opinions be about the world today?
10. Did they pass away from old age or something else? How did that affect you?

Your dad’s grandparents

11. What do you remember about your grandparents?
12. Were there any stories they passed down?
13. What were their hobbies or occupations?
14. What was your relationship with them like?

Your dad’s siblings

15. What was your relationship like with your siblings when you were a child?
16. What are your favourite childhood memories with them?
17. Do you have any regrets or missed opportunities in your relationship with them?

Your dad’s aunts, uncles, and cousins

18. Were you close to any of your aunts, uncles, or cousins?
19. Are there any special memories or traditions involving them?

Your dad’s friends

20. Who were your best friends growing up, and what made them special?
21. Who do you know the longest?
22. What was your social life like as a young adult?

Your family’s ancestors

23. Do you know any stories about notable family members or ancestors?
24. Is there a famous person or accomplishment associated with our family?
25. What’s a piece of family history that you think everyone should know?

People who influenced your dad

26. Did any friends or colleagues have a big impact on your life? What did they do?
27. Did anyone famous influence you? How did they influence you?

Connect every generation through the power of storytelling.

SIMIRITY APP

Conversation 3 – Early Relationship Years

You probably know how your parents met, but there is a wealth of really interesting stories to uncover with the following questions to ask your dad.

How your parents met

1. How did you first meet mom?
2. What were your first impressions?
3. Where did you meet, and what was the experience like?
4. Who made the first move, and how did that happen?
5. Were there any funny or memorable moments from your first meeting?

Dating

6. What was it like when you were dating mom?
7. Where did you usually go on dates?
8. How often did you see each other while you were dating?
9. How was dating back then different from dating today?
10. What was the moment you realised you wanted to marry mom?

The proposal

11. How did the proposal happen? Can you describe the backstory?
12. Was the proposal planned, or was it spontaneous?
13. How did you feel in that moment?
14. Were there any challenges or funny moments in preparing for the proposal?

The wedding

15. What was the preparation for your wedding like?
16. Who were the most important people involved in your wedding?
17. Where did you get married, and why did you choose that location?
18. Can you share any memorable moments from your wedding day?
19. Did you go on a honeymoon? Where did you go, and what was it like?

Life before kids

20. What did you do for fun before we were born?
21. How did your daily life look before starting a family?
22. Did you have any big dreams or plans for the future?
23. What hobbies or activities did you enjoy together before having kids?

Go beyond small talk—explore authentic family stories in Simirity.

SEE HOW

Conversation 4 – His Parenting Journey

Ever wondered what your father was really going through and thinking about while raising you? Uncover the backstory of your own childhood.

Pre-birth

1. Why did you decide to have kids?
2. Was it straightforward to conceive me (or my siblings)?
3. What were your thoughts and feelings when you first found out you were going to become a dad?
4. How was it supporting mom during her pregnancy?
5. What were some of your biggest fears or concerns before I was born?
6. How did you choose my name?

Birth

7. What do you remember about the day I was born?
8. What was your role during the birth?
9. What were the hospital and staff like?
10. What are your first memories of me after I was born?
11. What surprised you most about pregnancy and childbirth?

Early years

11. What was the most surprising thing about becoming a dad?
12. Were you ever scared to be a dad?
13. What parts of fatherhood did no one prepare you for?
14. Were there times you felt overwhelmed? How did you cope?
15. How did you handle the challenges of raising a child?

Fatherhood and identity

15. How did becoming a father change your sense of identity?
16. What did you learn about yourself after becoming a dad?
17. Were there any ways that parenthood affected your relationship with each other?
18. How did you balance (or struggle to balance) being a father with being yourself?
19. Did you feel pressure to be a “perfect dad”? How did you handle that?

Reflections on fatherhood

20. What kind of father did you want to be before we were born?
21. How did your own father influence your approach to parenting?
22. What aspects of fatherhood did you find most challenging?
23. Was there a moment when you truly felt like a father?
24. Did you ever feel unprepared or overwhelmed as a dad?
25. What do you wish you’d known about fatherhood before becoming one?
26. How has being a father changed you as a person?
27. If you could give one piece of advice to new fathers, what would it be?

Significant moments

28. What were some of the biggest challenges you faced as new parents?
29. What are your favourite memories of my childhood?
30. Were there any milestones that were especially significant or emotional for you?
31. What was the funniest or most unexpected thing I did as a child?

Approach to parenting

32. How would you describe your approach to parenting and why?
33. Is there something you wish you had done more of or less of as a parent?
34. What advice would you give to someone about to become a parent for the first time?
35. If you could go back and change anything about how you raised us, would you?
36. How did you cope with us during our terrible teens?
37. How did you react when we left home?

Grandparenthood

38. How does it feel to be a grandfather?
39. How is being a grandparent different from being a parent?
40. What advice do you have for us as future grandparents?
41. How could we make your experience as a grandparent even better?

Real-life family stories teach life’s greatest lessons.

SIMIRITY JOURNAL

Conversation 5 – Your Childhood Years

Your dad remembers things about your childhood that you probably don’t—these questions give you a backstage pass to your early years!

Your early traits and personality

1. Which of my characteristics do you think I inherited from you or other family members?
2. How would you have described me as a child?
3. What personality traits stood out about me when I was young?

Early memories and milestones

4. What was my favourite toy when I was a baby?
5. What were my first words?
6. Do you remember my first steps or any other early milestones?
7. What are some of your earliest memories of me as a child?

Family time and traditions

8. What were our favourite books or bedtime stories when I was young?
9. What’s a special tradition or routine we had during my childhood?
10. Can you share a memory of a family trip or vacation we took together?

Sibling and family dynamics

11. Can you describe my relationship with my siblings when we were all young?
12. Did I have a role in the family that stood out to you?

Favourites and aspirations

13. What was my favourite food or meal when I was growing up?
14. What were my dreams or aspirations as a child?
15. Was there something I always talked about wanting to be or do when I grew up?

Funny or surprising moments

16. What’s the funniest or most unexpected thing I did as a child?
17. Were there any habits or quirks I had that made you laugh or surprised you?

Family is forever—make sure their stories are too.

SIMIRITY JOURNAL

Practical Questions to Ask Your Dad

Some questions aren’t about nostalgia—they’re about preparation and taking responsibility for the future.

While communication channels are open with your dad, please take a moment to discuss the realities that affect your entire family.

Your dad’s medical history could save your life. His end-of-life wishes could spare you impossible decisions. His financial arrangements could prevent chaos during crisis. Fathers often carry this information silently, assuming there will be time later. But “later” arrives without warning.

The awkwardness of asking now is nothing compared to the challenge of not knowing when it matters most. 

Health & medical history

Your father carries information that could literally save your life. 

The health conditions that affected your grandparents, the heart disease that runs on his side, the cancer that appeared at specific ages—this isn’t just family trivia. It’s your genetic blueprint for preventive care. Knowing what to look out for means you can catch problems early and make lifestyle choices that minimise risks. 

1. What health conditions run in our family?
2. How did your parents and grandparents pass away?
3. What medical challenges have you faced personally?
4. Were there health issues that surprised you as you aged?
5. Looking back, what health decisions do you wish you’d made differently?
6. Has our family dealt with any hereditary conditions I should know about?
7. Are there any health risks you’d want us to monitor as we age?

Important arrangements and wishes

These conversations feel uncomfortable because they touch on loss—but that discomfort is temporary, while the clarity they provide is permanent.

These questions ensure your dad is in control over his own future, rather than forcing you to guess what he would have wanted at the worst possible moment. 

Have these discussions now, while he’s healthy and you’re both calm. Not later, when crisis forces uncomfortable questions in hospital hallways.

My dad was relieved when I finally brought this up. He’d organised everything but hadn’t known how to raise it without seeming morbid.

Legal/Financial:

1. Do you have a will? When was it last updated?
2. Who has power of attorney for healthcare decisions?
3. Who should we contact about financial matters if needed?
4. Where do you keep important documents (birth certificates, insurance policies, property deeds)?

Personal Wishes:

5. What brings you comfort when you’re unwell or stressed?
6. How would you want to be cared for if you became unable to live independently?
7. Are there specific people you’d want notified about major life events?
8. What matters most to you about maintaining dignity and independence?

Practical Details:

9. Who is your primary doctor, and how can we reach them?
10. What medications do you take regularly?
11. Do you have any advance directives or living wills?
12. What’s the password/location for your important online accounts?

Legacy Wishes:

13. Is there anything special you’d want done with particular possessions?
14. Are there any messages or wisdom you’d want passed to future generations?
15. What would you want your obituary to emphasise?

28 Must-Ask Follow-up Questions 🤔

Follow-up questions are the key to unlocking deeper, more meaningful conversations with your dad.

While initial questions help start a dialogue, follow-ups show that you’re truly listening and invested in his answers. They encourage your dad to share his emotions, reflect on his experiences, and provide new perspectives that might otherwise remain untold.

By asking these more intimate follow-up questions to your dad, you can uncover the rich details and layers behind his stories, helping you get to know him better as you understand his life experiences more deeply.

Emotional responses

• How did you feel about that?
• What emotions did that bring up for you?
• Did that make you happy, or was it difficult for you?
• What was the most exciting part of that experience?
• How did you handle that situation emotionally?
• Looking back, do you think you’d feel the same way now?

Personal reflections

• Did you enjoy that? Why or why not?
• Looking back, would you have done anything differently?
• What do you think you learned from that experience?
• How did that experience shape who you are today?
• Do you ever think about that moment now?
• What advice would you give to someone facing a similar situation?

Deeper insights

• Why do you think that happened the way it did?
• What was the hardest part of going through that?
• Did anyone help you during that time?
• How did you make that decision?
• Was there anything you wished you’d known back then?

Connections and relationships

• How did that affect your relationship with [specific person]?
• Did you talk about this with anyone at the time?
• What do you think your parents (or siblings) felt about that?
• Was that something your friends or family also experienced?

Hindsight and perspective

• Any regrets about how things turned out?
• What would you tell someone going through the same thing now?
• Was there anything you overlooked or didn’t realize at the time?
• Do you think you’d handle that situation differently today?
• Did that experience teach you any life lessons?

Fun and nostalgic prompts

• What’s the funniest thing that happened during that time?
• Did you have a favourite memory from that experience?
• Were there any inside jokes or stories tied to that?
• What do you miss most about that time in your life?

Free Download: All Interview Questions to Ask Your Dad 📥

Ready to start these meaningful conversations?

Download our free guide with all 350+ questions to ask your dad, organised into 13 themed conversations — plus memory book templates your dad can fill out independently.

What you’ll get:

1. Getting Started Guide – Tips for choosing the right approach for your family.
2. Memory Book Templates – Two Word documents (Essential & Complete editions) your dad can complete on his own.
3. Conversation Guide PDF – All 350+ questions across 13 themes for guided discussions. You’ve seen the first five conversations, but there are eight more in the guide (Life-Long Learning, Career, Hobbies and Interests, Travel and Places, Challenges and Milestones, Witnessing Historical Changes, Reflections on Life, Retirement and the Future).

BONUS – 7 Tips for Asking Your Dad Questions

Here are some tips to help you use the conversation guide with your dad in the most effective way.

1. Print the guide and highlight your must-ask questions

Not all the questions provided will feel right for you or your dad. Be selective.

In preparation for your interview, we print the PDF with the list of questions and highlight the essential questions to ask your dad. These ‘must-ask’ questions can help keep your discussion on track if it gets sidetracked (and it will).

2. Choose the right time and place

Setting the stage for your discussion can make a world of difference.

Here are some key points to consider:

• Pick a moment when your dad is relaxed
• Allow sufficient time to not feel rushed
• Ensure the environment is free from distractions

I found that my dad appreciated being told ahead of time about my plan to ask him questions about his past. I didn’t share all the questions ahead of time to avoid him preparing answers that felt staged (more on that later).

3. Start with easy, fun questions

Begin the session with fun and simple questions that put your dad at ease.

We’ve tried to organise the question list with this in mind, but adjust according to your dad. You’re looking to get your dad into his comfort zone, where he can enjoy himself in a relaxed atmosphere.

It’s a great way to set the tone for deeper discussions later.

4. Be patient and open to tangents and small talk

Some of the best stories emerge when you let the discussion flow naturally.

Your dad might veer off-topic or share something unexpected. Embrace these moments as they often reveal insights and memories you wouldn’t think to ask about.

I recorded the audio of all our conversations, and listening back to them reminds me how precious small talk can be. These authentic interactions capture what he’s really like in day-to-day life, which is how I want to remember him.

5. Actively listen and ask follow-up questions only when he’s finished

“The art of conversation lies in listening.”
— Malcolm Forbes

We recommend asking follow-up questions only when the line of conversation seems to be exhausted. Give him the time he needs — often the best answers don’t come immediately to mind.

TIP – When you sense the topic has reached an end, try waiting a little longer before asking something new. Doing so creates a little tension, and if he was holding back, he might decide to share it after all.

6. Make it a flow — it shouldn’t feel like an interview!

Think of your list of questions as a rough guide designed to spark insightful discussions. Pick and choose what works for you, and be open to exploring the topics that arise even if they weren’t planned.

Here is an ideal conversation flow:

1. Ask your question and see where it takes you.
2. Give your dad time, and a little extra, to tease out stories.
3. Prompt him with ideas if he is struggling.
4. Pose the next question when your topic has reached a natural end.

7. Ensure your dad’s stories are preserved for your children

These are REAL stories about your dad that have SHAPED your family’s lives. They are not Netflix dramas or fiction books that can be listened to and forgotten!

Preserve the stories your dad shares—they are an essential part of your family’s legacy. Why sharing family stories matters.

Wouldn’t it be amazing if you could learn about the lives of your ancestors? That’s the gift that YOU can give YOUR future family!

• Save them in life story books like Storyworth.com.
• Write a physical book with all your family stories that you can pass on to your children.
• Record your discussions as audio files and upload them to Google Drive so all your family can access them.
• Or digitise memories on Simirity, a platform our family built to be the online home of all family stories. Privately share media-rich stories that include voice recordings, written stories, photos, videos, and so much more. Best of all, with digital storytelling everyone in your family can access it and future generations can join to be welcomed with stories from their family’s past.

Browse our demo account to see families preserving stories from fathers and everyone in their family. See how Simirity compares to other family journaling apps.

3 Reasons to Have These Conversations Soon

1. Deepen connections as you get to know your dad better

Posing thoughtful questions enables you to view your dad in a new light, beyond his parental role.

These open-ended interview questions to ask your dad spark meaningful conversations that help you get a deeper understanding of his emotions, experiences, ambitions and values.

When we surveyed parents, 60% agreed that their regular family conversations ‘followed similar patterns and themes‘. Nice as these discussions were, they hoped for topics with a bit more intimacy that they could bond over.

My only regret is not asking my dad these questions earlier, as I now know him on a far deeper level.

2. Discover how your life has been shaped by your family history

Knowing your family’s story is key to understanding your own.
— Unknown

It’s important to gain insights into your dad’s life, for selfish reasons as well as altruistic ones. His experiences can help you understand your personal history and can also help you overcome personal challenges and improve your well-being.

When I asked these questions to my dad, I realised that so many characteristics of family today have their roots in the past. The expectations his parents had of him, the environment he grew up in, and the difficult times he faced influenced so many familial traits and family values. Many of which I am unintentionally passing on to my own children.

It’s curious to contemplate how much of our identity and values stem from times before our birth.

3. Gain new insights that make future conversations more rewarding

Uncovering new details about your dad’s life transforms the way you interact. These insights bring fresh energy to future conversations and make it easier to connect over shared understanding.

After I had explored these questions with my dad, I frequently caught myself referring back to his experiences in our conversations. We were no longer stuck in trivial exchanges about present-day family updates but had a solid foundation to refer back to. And we gained a new set of conversation starters, which adds interest to our regular catch-up calls.

Preserving our family’s stories and imagining how precious they will be to future family, gave me an unparalleled sense of purpose and achievement. These stories are nothing short of our most precious family legacy.

Take the first steps today with your family; don’t wait until it’s too late.

— Andrew Ronald (Simirity Founder)

FAQs About Asking Dad Meaningful Questions

Still not sure how to go about interviewing your dad? Review these frequently asked questions to fill in the gaps.

Should I consider sharing questions with him before our conversation?

There are some good reasons to share, but it can come at a cost.

Advantages

1. He can find supporting photos, heirlooms or documents that accompany his answers.
2. Some questions are a bit tricky or may require time to reflect. Questions like “is there anything in life you regret?” may benefit from being shared ahead of time.

Disadvantages

1. If you share questions, his answers might feel staged and less authentic.
2. Some dads might feel stressed ahead of the conversation.

What is a good way to start?

Before the conversation, it can help to explain why you want to talk to him.

When you start, icebreakers may help ensure that he feels relaxed and open to sharing. Try leading by example — talk openly and in the manner you wish him to reply.

Should I take notes during our conversation?

It’s good to note down any follow-up questions you would like to ask as the conversation evolves, but we would not recommend trying to write down all his answers, as you cannot be fully present in the moment. Instead, try recording your conversation so no detail gets forgotten.

How can I record our conversation?

I strongly recommend recording your conversation in some way—you’ll be grateful you did. Video recordings are especially valuable because they preserve not only words, but also the emotions behind them. Seeing your dad’s smile as he recalls a happy memory, or watching him gesture as he tells a story, will be wonderful to look back on.

Video recording tips:

• Your smartphone is perfect – no fancy equipment needed.
• Position it slightly off to the side (more natural than center).
• Ensure good lighting (face a window if possible).
• Check audio in the actual room first – soft furnishings improve sound.
• Start recording before the conversation begins to capture natural moments.

Video feels too much? Audio still captures far more than written notes. Use iPhone Voice Memos or an app like this one for Android. The key is preserving his actual voice and the way he tells stories.

How much time will these conversations take?

A good conversation is like a miniskirt: short enough to retain interest, but long enough to cover the subject.
— Celeste Headlee

Spending time talking about things that really matter shouldn’t be rushed. In our experience, you will want at least one to two hours to address each of the 13 conversation themes. If they drag on too long, you’ll run out of momentum, so take breaks as needed.

How can I ask my dad a hard question?

There may be challenging aspects from your dad’s past that you would like to learn more about and gain his perspective on. You may think that asking your dad a hard question like ‘why did you separate from my mom?’ is not possible, but I challenge you to reconsider, as the potential upside if he does answer could be significant.

It’s very important to never start out with a tough question — warm him up with fun questions so he feels comfortable first.

Tough though they may be, the hard questions are often the most rewarding, giving you a deeper level of understanding that strengthens your bonds.

What should I do if he is reluctant to answer?

Firstly, be aware that our minds have a habit of playing tricks on us—building an imaginary narrative of how others might react. The only way to really know is to ask, and you can do so without offence with the following tips:

1. Respect his boundaries. Acknowledge his feelings and let him know it’s okay if he’s not ready to share. Example: “I understand if this is hard to talk about. We can move on if you’d prefer.”

2. Approach gently. Introduce sensitive topics indirectly or in a lighter way to ease into the conversation. Example: “I was wondering about what life was like for you growing up, but only if you’re comfortable sharing.”

3. Show empathy. Let him know why his stories matter to you and that you’re coming from a place of care and curiosity. Example: “I’d really love to understand your experiences more—it helps me feel better understand your train of thought.”

4. Reframe the topic. If he resists a certain topic, try approaching it from a different angle. Example: Instead of asking directly about a painful time, ask, “How did you find strength during that period?”

5. Share your own experiences. Share something personal first to encourage reciprocity. Example: “I sometimes feel overwhelmed with [specific challenge]. Did you ever feel like that?”

6. Focus on positives. Frame questions in a way that emphasises resilience or growth. Example: “What did you learn from that experience?” or “Was there anything good that came out of that difficult time?”

7. Offer an alternative format. Suggest discussing difficult topics in a less direct way—could he write them down and share them that way?

8. Give him time. Let him process his thoughts. If he’s not ready now, ask if you could revisit the topic later. Example: “No pressure to talk about this now—we can come back to it anytime you feel comfortable.”

Are these interview questions good for my grandfather too?

Yes, they are great for grandfathers.

They’ll need to be done differently in places — for example the questions about your childhood should be reframed towards your parents’ childhood. His memories of your childhood would be a bonus question!

Other Ways to Bond With Your Dad

Here are some other ways to connect with your dad and the rest of your family.

• Use family journal ideas to uncover even more discussion topics.
• Explore new horizons with 200 thought provoking ‘would you rather’ questions for families.
• Discover the stories behind your family’s heirlooms.
• Involve all family generations with 19 fun family challenges that teach valuable life skills.
• Start a new hobby that you can enjoy together—here are 25 fulfilling activities that are suitable for grandparents.

Don’t Forget Your Free Resources!

Download the complete conversation guide (350+ questions to ask your dad), memory book templates, and getting started tips—everything you need to preserve your father’s stories.