350+ Questions to Ask Your Dad Plus a List-Building Tool

Andrew Ronald

Simirity Founder | Father of two

17th October, 2025

How well do you really know your dad?

Finding the right questions to ask your dad is harder than it sounds. I was fortunate to have a dad who was always ready to share stories — 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, that I’ve realised how much about his life I’ve never thought to explore. Thankfully, I didn’t wait too long.

This page gives you everything you need to start. Browse five of our 13 themed conversations below and use the list-building tool to bookmark the questions that feel right for your dad. When you’re ready to go further, download our free guides — including printable memory books he can fill in himself, and the complete 350+ question conversation guide across all 13 themes.

Your First 5 Conversations With Dad

Work through the conversation themes below and save the questions you want to ask your dad. Your list builds as you go.

For a similar experience with your mom, try these questions to ask your mom.

Memory Book for Dad vs Guided Conversations

A memory book is a guided journal — a curated set of questions covering all phases of life that he completes in his own time, at his own pace. No conversation required, no scheduling, no pressure.

Our Essential and Complete editions are both free to download, and many families find it’s the easiest way to start capturing the foundations: where he grew up, his education, his career, the key moments of his life.

But they have a blind spot.

Predictable questions lead to predictable answers—and the stories that actually reveal who she is rarely make it into the book.

Ask your dad in writing: “What were your teenage years like?” You’ll probably get something like: “Pretty typical. Went to school, had a few close friends, worked part-time at the local shop.” Accurate — but not what you were hoping for. Memory books capture what your dad thinks you want to know. They rarely surface what you actually want to hear.

A memory book will tell you where your dad was born and what job he had. It won’t tell you why he chose that path, what he gave up along the way, or what he was really thinking when he became a father.

That’s where guided conversations go so much further. In a conversation, that same question about his teenage years becomes a thread you can pull — what was typical for that era, what school was actually like, what he and his friends used to get up to. You uncover questions you never thought to ask, and he shares stories he never thought to tell.

When I searched for conversation guides to use with my own father, I found nothing worth using — hundreds of disconnected questions with no structure or flow. So I created my own conversation guides — thirteen themed conversations, each designed to explore one chapter of his life at a time.

Those conversations with my father 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.

The best approach? Both. Start with the memory book to capture the foundations. Use the conversation guide to explore the stories behind them. The four free guides below give you everything you need for either approach.

Going Beyond The First 5 Conversations

The list builder above covered 5 of our 13 conversation themes. When you’re ready to go further, the free Conversation Guide below includes all 13 — from his career and travels to his reflections on life and what he hopes for the future. Each theme is designed to fill an hour or two, so there’s no need to rush. Pick one, find a quiet moment, and let the conversation lead where it will.

1. Childhood and Family History
2. Family and Friends
3. Early Relationship Years
4. Her Parenthood Journey
5. Your Childhood years
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)

Everything you need to start the conversation and preserve what you hear

What you’ll get:

1. Getting Started Guide – Not sure which approach is right for your family? This short guide helps you choose the right approach to storytelling in your family.
2. Memory Book Templates – Two Word documents your dad can complete in his own time, at his own pace. The Essential edition covers the foundations (25 questions). The Complete edition goes deeper (65 questions). Give him one and let him fill it in — no conversation required.
3. Conversation Guide PDF – All 350+ questions to ask your dad organised into 13 themed conversations. The list builder above covers the first five themes. This PDF gives you all thirteen — including Life-Long Learning, Career, Hobbies, Travel, Challenges, Historical Changes, Reflections on Life, and Retirement.

Must-Ask Follow-up Questions

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

The best conversations don’t follow a script. Once your dad starts talking, these follow-up questions help you go deeper — past the facts and into the feelings, the context, and the stories he wouldn’t have thought to share on his own.

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?

The Conversations That Are Easy to Put Off

Some questions aren’t about nostalgia. They’re about preparation.

While you’re having meaningful conversations with your dad, use this opportunity to discuss practical matters that affect your health and future planning. I found these topics initially awkward to discuss. But it was a great relief to finally address them.

You’re not being morbid or intrusive, just thoughtful and prepared.

Health & medical history

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?

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?

Tips for Better Conversations With Your Dad

Here are seven tips to help you use these conversation starters with your dad in the most effective way.

1. Print out and highlight your must-ask questions

Not all questions will feel right for you or your dad — be selective. Use the list builder above to save your must-ask questions before the conversation, so you have a focused list rather than hundreds to scroll through.

In preparation for your interview, we recommend printing the PDF with the list of questions and highlighting 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 her questions about her past. I didn’t share all the questions ahead of time to avoid her preparing answers that felt staged.

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 her 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. 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 she’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 they’ve 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 they were holding back, they 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 conversations will produce real stories — about real people who shaped your family’s life. Don’t let them live only in your memory. Record the audio, and find somewhere to keep it that the whole family can access.

We built Simirity specifically for this: a private family journal where voice recordings, photos, videos, and written stories live together in one place, privately shared with everyone who matters. The conversations you have with your mom deserve more than a folder on Google Drive.

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

Why You Should Have These Conversations Soon

1. You’ll discover who he really is, beyond his role

When we surveyed parents, 60% said their regular family conversations followed similar patterns and themes. Comfortable, yes, but rarely revealing. Thoughtful questions take you somewhere different. Past the routines and the parental role, into the person he was before you knew him — his ambitions, his fears, the experiences that shaped his values.

My only regret is not asking these questions earlier.

2. You’ll understand yourself differently

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

His story is part of your story.

The expectations his parents had of him, the environment he grew up in, the difficult times he faced — these shaped your family in ways that are still playing out today. Many of which you’re probably passing on to your own children without realising it.

Knowing your family’s history is one of the most clarifying things you can do for your own sense of identity.

3. Time matters more than you think

The conversations you have now become the stories your family tells forever. Once they’re gone, they’re gone — not just for you, but for your children and grandchildren who will never have the chance to ask.

Preserving these stories gave me an unparalleled sense of purpose. They are nothing short of our most precious family legacy.

Don’t wait until it’s too late.

— Andrew Ronald (Simirity Founder)

Other Ways to Bond With Your Dad

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

• Use family journal ideas to uncover even more discussion topics.
• Play the how well do you know your family game, to test your knowledge of your mom, and bookmark the unknowns to prompt a follow-up conversation with her. Works for other family members too.
• For dads who don’t like to be in the spotlight, try the Family Story Game. Your mom and up to 7 others take turns drawing life-related question cards. Questions are tailored to your stage of life, so everyone from grandchildren to grandparents gets questions relevant to them.
• Start a new hobby that you can enjoy together—here are 25 fulfilling activities that are suitable for grandparents.

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 questions to ask my dad 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!