350+ Thought Provoking Questions to Ask Your Mom and Dad

How well do you really know your parents? These questions to ask your mom and dad will help you find out.

I thought I knew everything about the people who raised me — their favourite sayings, quirks and passions. But beneath those familiar habits lay a world of untold stories and life lessons that shaped their lives and unbeknownst to me, my life too. 

Asking thought provoking questions goes beyond curiosity — it’s about understanding your mom or dad, deepening your bond with them, and finding inspiration from their experiences. Most importantly, asking these questions gives you a chance to preserve your family history before it’s too late. Once someone is gone, their stories become irreplaceable treasures, more precious than any heirloom. 

In this guide, you’ll find over 350 thought provoking questions to spark meaningful conversations — like asking about their proudest moments, challenges they’ve overcome, or childhood recollections. To avoid overwhelm, we’ve created 13 themed conversations with questions organised accordingly. 

Scroll down for first 5 converstions or download a PDF guide with all 13 conversations and 350+ questions.

Jump to section:

• 3 Benefits of Asking Thought Provoking Questions
• 13 Themed Conversations With 350+ Simple Questions to Ask Your Mom and Dad
• Conversation 1 – Childhood Years and Family History  
• Conversation 2 – Family and Friends
• Conversation 3 – The Early Years of Their Relationship
• Conversation 4 – Their Parenting Journey 
• Conversation 5 – Your Childhood Through Their Eyes
• 30 Must-Ask Follow-up Questions
• Free PDF Download: All Questions to Get to Know Your Parents
• BONUS – 7 Tips for Asking Your Parents Questions
• Ask Your Parents Right Now, Don’t Delay!
• FAQs about Asking Meaningful Questions 
• Other Ways to Bond With Your Parents

Ready to discover a whole new side of your parents? Let’s dive in!

3 Benefits of Asking Thought Provoking Questions

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

Posing thoughtful questions enables you to view your mom or dad in a new light, beyond their roles as your caregivers. 

These open-ended questions to ask your mom or dad 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 these questions earlier, as I now know my parents 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 parents’ lives, for selfish reasons as well as altruistic ones. Their 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 and dad, I realised that so many characteristics of family today have their roots in the past. The expectations their parents had on them, the environment they grew up in, and the difficult times they faced, influenced so many familial traits. 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 parents’ lives transforms the way you interact. These insights bring fresh energy to future conversations and make it easier to connect over shared understanding.

After my family had explored these questions, I caught myself so many times referring back to their 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. 

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

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

Find a theme that interests you, identify the questions you would like to ask (print the PDF and highlight) and prepare the environment for questioning. Based on my family’s experience, I would recommend allowing at least one hour, ideally two, for each conversation. 

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

Conversation 1 – Childhood Years and Family History  

Discover the stories that shaped your parents’ early years and family background with these questions, designed to uncover meaningful memories and insights about their childhood and upbringing.

1. Family origins

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

2. First memories

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

3. Early life

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

4. Teenage years

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

5. Becoming independent

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

6. Traditions and customs

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

Conversation 2 – Family and Friends

Family and friends are the cornerstones of life. These questions help you uncover the connections, relationships, and stories that shaped your parents’ world, offering a deeper understanding of the people who influenced them most.

Your mom or dad’s parents

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

Your mom or dad’s grandparents

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

Your mom or dad’s siblings

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

Your mom or dad’s aunts, uncles, and cousins

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

Your mom or dad’s friends

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

Your family’s ancestors

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

People who influenced your mom or dad

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

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 questions below. Posing these questions to both parents at the same time can make for a lively and enlightening discussion.

How your parents met

• How did you first meet?
• What were your first impressions?
• Where did you meet, and what was it like?
• Who made the first move, and how did that happen?
• Were there any funny or memorable moments from your first meeting?

Dating

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

The proposal

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

The wedding

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

Life before kids

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

Conversation 4 – Their Parenting Journey 

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

Pre-birth

• Why did you decide to have kids?
• Was it straightforward to conceive me (or my siblings)?
• What were your thoughts and feelings when you first found out you were going to become parents?
• How was it being pregnant with me?
• What were some of your biggest fears or concerns before I was born?
• How did you choose my name?

Birth

• What do you remember about the day I was born?
• What was dad’s role during the birth?
• What were the hospital and staff like?
• What are your first memories of me after I was born?

Early years

• What was the most surprising thing about becoming a parent?
• Were you ever scared to be a parent?
• Were there times you felt overwhelmed? How did you cope?
• How did you handle the challenges of raising a child?

Impact on you

• How did becoming a parent change you?
• What did you learn about yourself after becoming a parent?
• Were there any ways that parenthood affected your relationship with each other?

Significant moments

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

Approach to parenting

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

Grandparenthood

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

Conversation 5 – Your Childhood Years

Your parents remember 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

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

Early memories and milestones

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

Family time and traditions

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

Sibling and family dynamics

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

Favourites and aspirations

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

Funny or surprising moments

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

28 Must-Ask Follow-up Questions

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

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

By asking these more intimate follow-up questions, you can uncover the rich details and layers behind their stories, helping 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 favorite 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 PDF Download: All Questions to Get to Know Your Parents

To make it even easier to start talking with your mom or dad, we’ve created a free resource to help. Download a PDF featuring the following 13 conversation themes with 350+ questions.

The 13 conversation themes:

1. Childhood and Family Background 
2. Family & Friends
3. Early Relationship Years
4. Their parenthood journey 
5. Your Childhood Years 
6. Life-Long Learning (Exclusive to PDF)
7. Career (Exclusive to PDF)
8. Hobbies and Interests (Exclusive to PDF)
9. Travel and Places (Exclusive to PDF)
10. Challenges and Milestones (Exclusive to PDF)
11. Witnessing Historical Changes (Exclusive to PDF)
12. Reflections on Life (Exclusive to PDF)
13. Retirement and the Future (Exclusive to PDF)

This resource is perfect for guiding your discussions, ensuring you never run out of thoughtful topics to explore. Download it now and create moments that truly matter.

BONUS – 7 Tips for Asking Your Parents Questions

Anything worth doing is worth doing well.

— Hunter S. Thompson

Here are some tips to help you ask your mom and dad the right way.

1. Print out and highlight your must-ask questions

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

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

We found that our parents appreciated being told ahead of time about our plans to ask them questions about their past. We didn’t share all the questions ahead of time to avoid them 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 parents at ease. 

We’ve tried to organise the question list with this in mind, but adjust according to your family. You’re looking to get them in their comfort zone, enjoying themselves 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 parents might veer off-topic or share something unexpected—embrace these moments. They often reveal insightsand 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 they are really like in day-to-day life, which is how I want to remember them.

5. Actively listen and ask followup 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 them the time they need — 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 them time, and a little extra, to tease out stories.
3. Prompt them with ideas if they are struggling.
4. Pose the next question when your topic has reached a natural end.

7. Ensure these family stories are preserved for your children

These are REAL stories, about people you LOVE, 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 parents share – they are an important part of your family’s legacy. 

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 or Storied.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 them on our own platform, Simirity.com, which 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, everyone in your family can access it and future generations can join to be welcomed with stories from their family’s past.

If you would like to learn more about Simirity App, visit our home page.

Ask Your Parents Right Now, Don’t Delay!

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 and Dad Meaningful Questions 

Still not sure how to proceed? Review these frequently asked questions to fill in the gaps. 

Should I consider sharing questions with them before our conversation?

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

Advantages

1. They can find supporting photos, heirlooms or documents that accompany their 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, their answers might feel staged and less authentic.
2. Some parents 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 them.  

When you start, icebreakers may help ensure that they feel 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 conversion evolves, but we would not recommend trying to write down all their 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?

Recording the conversation is a great way to ensure the details are preserved, even if it’s just for you to transcribe later. All iPhones have voice memos built in and you can download an app like this one on Android devices. Alternatively, you can video your conversations.

Consider asking for their approval to use voice or video recordings well ahead of your discussion.

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 conversation theme. If they drag on too long, you’ll run out of momentum, so take breaks as needed.

Should I ask my parents at the same time?

If you are fortunate enough to be able to ask both parents at the same time, two minds really can be better than one on the following conversation themes:

1. Early Relationship Years 
2. Their Parenthood Journey 
3. Your Childhood Years 
4. Life Long Learning  
5. Travel And Places  
6. Hobbies And Interests  
7. Life Challenges and Milestones
8. Witnessing Historical Changes
9. Reflections On Life  
10. Retirement And The Future

How can I ask my parents a hard question?

There may be challenging aspects of your parents’ past that you would like to learn more about and gain their perspective on. You may think that asking your parents 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 they do answer could be significant.

It’s very important to never start out with a tough question – warm them up with fun questions so they feel 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 they are 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 their feelings and let them know it’s okay if they’re 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 them know why their 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 they resist 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 emphasizes 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 they write them down and share them that way?

8. Give them time. Let them process their thoughts. If they’re 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 thought-provoking questions good for my grandparents too?

Yes, they are great for parents and grandparents alike.

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 Parents

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

• Explore new horizons with 100 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.