350 Eye-Opening Questions to Ask Your Mom

Andrew Ronald

Simirity Founder | Father of two

17th October, 2025

How well do you really know your mom? These 350+ questions to ask your mom will guide you towards engaging conversations that reveal her in a new light.

I thought I knew everything about the woman who raised me—key moments from her life, her favourite sayings, quirks and passions. But when I finally asked the right questions, I discovered a whole world of untold stories and life lessons that shaped not just her life, but mine too.

Asking these questions takes you on a shared voyage of discovery while preserving her experiences and personality so they won’t be forgotten.

Choose how you want to explore your mother’s story

Every mother is different. Your mom might prefer the quiet reflection of answering questions in a guided memory book at her own pace. Or she might love sitting down for long, meaningful conversations that explore her life more deeply. Both paths lead to the same precious destination: connecting with your mother as you explore her experiences and thoughts on life.

We help with both approaches:

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

Understanding your mom goes beyond curiosity—it’s about deepening your bond, finding inspiration from her experiences, and preserving family history before it’s too late. Once someone is gone, their stories become irreplaceable treasures, more precious than any heirloom. ⏳ 

Jump to section:

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

Memory Book for Mom vs Guided Conversations

Start with a memory book: The foundational approach

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

Why memory books are a great starting point:

• Hands-off simplicity — Give her the book and she takes it from there.
• Independent completion — Your mom works through it on her own timeline.
• Time to reflect — She can think deeply about her 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.

Step up to guided conversations: Going much deeper

Memory books excel at capturing foundational stories, but they have a blind spot!

They’ll tell you where your mom was born and what job she had, but not why she chose that path or what kept her up at night. They capture the what and when, but rarely the why and how it felt. They ask about motherhood but not about the identity shift that comes with it.

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

That’s where our conversation guides make all the difference.

When I wanted to explore my own mother’s story more deeply, I searched for conversation guides 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 mom.

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

Why guided conversations are so much more valuable:

• Depth and authenticity — Your mom’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 contain many more questions than typical memory books, exploring topics most books never touch.
• Natural discovery — You can ask follow-up questions immediately, uncovering stories she’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 mother 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—which is a great idea! 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 mom’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 Mom

Organising questions by themes helps create a more focused and enjoyable conversation. It allows you to explore one area of your mom’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. Her 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 mom’s early years and family background. These questions to ask your mom will help you uncover meaningful memories and insights about her 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 mom uncover the connections, relationships, and stories that shaped her world, offering you a deeper understanding of the people who influenced her most.

Your mom’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 mom or 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 mom or 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 mom or 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 mom or 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 mom or 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 mom.

How your parents met

1. How did you first meet dad?
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 dad?
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 dad?

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/waiting for the proposal?
15. How did expectations for women and marriage differ back then compared to today?

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 – Her Parenting Journey 

Ever wondered what your mother 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 mom?
4. How was it being pregnant with me?
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 dad’s 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 mom?
12. Were you ever scared to be a mom?
13. What parts of motherhood 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?

Motherhood and identity

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

Significant moments

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

Approach to parenting

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

Grandparenthood

28. How does it feel to be a grandmother?
29. How is being a grandparent different from being a parent?
30. What advice do you have for us as future grandparents?
31. 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 mom 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 Mom

Some questions aren’t about nostalgia—they’re about preparation.

While you’re having meaningful conversations with your mom, 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

These questions help you to be proactive about your family’s health. Your parents’ and grandparents’ medical history can help you optimise medical checkup frequencies and lifestyle choices. Your mom’s experiences might help you catch problems early or avoid pitfalls they encountered.

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.

By asking the following questions, you’re respecting your mom’s wishes, simplifying what comes later, and avoiding making difficult decisions without their guidance. It’s far better to have these discussions now, while everyone’s healthy and calm, rather than putting it off until circumstances force the conversation. 

My mom actually appreciated it when I raised these topics, and it gave us a chance to address the issues that had been overlooked.

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 mom. 

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

By asking these more intimate follow-up questions to your mom, you can uncover the rich details and layers behind her stories, helping you get to know them better as you understand their 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 Mom 📥

Ready to start these meaningful conversations?

Download our free guide with all 350+ questions to ask your mom, organised into 13 themed conversations — plus memory book templates your mom 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 mom can complete on her 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 Mom Questions

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

1. Print out and highlight your must-ask questions

Not all the questions provided will feel right for you or your mom. Be selective — don’t ask them all!

In preparation for your interview, we recommend printing the PDF with the list of questions and highlighting the essential questions to ask your mom. 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 mom is relaxed
• Allow sufficient time to not feel rushed
• Ensure the environment is free from distractions

I found that my mom 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 (more on that later).

3. Start with easy, fun questions 

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

We’ve tried to organise the question list with this in mind, but adjust according to your mom. You’re looking to get your mom into her comfort zone, where she can enjoy herself 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 mom 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 her.

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 her the time she 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 mom time, and a little extra, to tease out stories.
3. Prompt her with ideas if she is struggling.
4. Pose the next question when your topic has reached a natural end.

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

These are REAL stories about your mom 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 mom 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 parents 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 mom better  

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

These open-ended interview questions to ask your mom spark meaningful conversations that help you get a deeper understanding of their 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 mom these questions earlier, as I now know her 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 mom’s life, for selfish reasons as well as altruistic ones. Her 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 mom, I realised that so many characteristics of family today have their roots in the past. The expectations her parents had of her, the environment she grew up in, and the difficult times she 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 mom’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 mom, I frequently caught myself referring back to her 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 Mom Meaningful Questions 

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

Should I consider sharing questions with her before our conversation?

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

Advantages

1. She can find supporting photos, heirlooms or documents that accompany her 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, her answers might feel staged and less authentic.
2. Some moms 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 her.  

When you start, icebreakers may help ensure that she feels relaxed and open to sharing. Try leading by example — talk openly and in the manner you wish them 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 her 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 mom’s smile as she recalls a happy memory, or watching her gesture as she 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 her actual voice and the way she 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 mom a hard question?

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

It’s very important to never start out with a tough question — warm her up with fun questions so she 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 she 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 their boundaries. Acknowledge her feelings and let her know it’s okay if she’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 her know why her 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 she 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 she write them down and share them that way?

8. Give her time. Let her process her thoughts. If she’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 grandmother too?

Yes, they are great for grandmothers.

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

Other Ways to Bond With Your Mom

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.
• 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 mom), memory book templates, and getting started tips—everything you need to preserve your mother’s stories.