10 Questions to Ask Your Mom (or Grandma) Today

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Mother’s Day just passed, and it got me thinking about the incredible stories moms and grandmas hold. Those conversations aren’t just about nostalgia, though. They’re the heart of your family history.

If you’ve ever felt stuck in your family history search or overwhelmed about where to start, talking with your mom (or grandma) can open doors you didn’t even know existed.

But how do you turn that conversation into something truly meaningful? How do you create a space where stories flow easily and memories come to life? That’s exactly what we’ll explore today!

Plus, I’ve gathered 10 thoughtful questions to ask your mom (or grandma) to help you get started. Whether you're new to family history or have been poking around for a while, a good question is often the best place to begin.

Before we get more into it, hi! I’m Jessica, a professional genealogist with 20 years of personal experience and five years working with clients across the U.S. and Canada. I specialize in family history research for Hawaii, New England, and French Canada. My passion is helping people discover their roots and understand the real lives behind the names in their family trees. Whether you’re brand new to genealogy or you’ve been poking around old records for years, I’m here to make the journey easier and more meaningful.

Okay! Before we dive into the questions, let’s talk about setting the scene for a great conversation.

Image by Logan Weaver on Unsplash

Why This Conversation Matters and Tips for Creating a Comfortable, Storytelling Atmosphere

Alright, now here’s something that really makes a difference when you’re ready to have that conversation: creating a relaxed, comfortable space. I’ve found that storytelling flows best when the setting feels cozy and pressure-free.

Try pulling out some old photos during your chat. Pictures have this magical way of unlocking memories that might have been tucked away for years. (I often find myself getting lost in the details of a faded black-and-white photo, imagining the lives behind those smiles.)

Think about sitting somewhere comfortable, maybe around the kitchen table or curled up on the couch with a warm drink. Let your mom or grandma know there’s no rush and no “right” answers, just stories waiting to be shared whenever they’re ready. Often, the best memories come out when everyone feels relaxed, and the conversation flows naturally.

Ask follow-up questions like "How did that make you feel?" or "What happened next?" These help deepen the story and show that you’re genuinely engaged.

It’s also important to be mindful of emotions. If something seems painful or brings up discomfort, be respectful. Change course or come back to it later. Some stories need time.

Struggling to keep your genealogy research on track? This blog teaches you how to break your tasks into easy time blocks, so you can make steady progress without feeling overwhelmed.

Start the Conversation: 10 Questions to Ask Your Mom (or Grandma)

1. What is one memory from your childhood that still makes you smile?

Starting with something positive and light sets a warm tone. Childhood memories often reveal so much about the person behind the family story, like their joys, friendships, and little everyday moments that shaped who they became. You might hear about a favorite game, a holiday tradition, or a funny mishap that still gets talked about today.

2. How did you meet Dad (or Grandpa)?

Love stories are family treasures. Asking this invites your mom or grandma to share their early romance, how they met, and what those first days felt like. These stories often include details you won’t find in any official record, like secret meeting spots, little acts of kindness, or quirky first impressions. (I love hearing these—it’s like piecing together a family romance novel.)

3. What traditions or customs were most important to your family growing up?

Traditions shape identity and connect generations. Whether it was a special holiday, a Sunday dinner routine, or a unique custom tied to your cultural roots, these stories tell you what your ancestors valued most. And they give you clues on how to keep those traditions alive today. Plus, these stories often lead to deeper questions about religion, ethnicity, or how ancestors adapted to life in a new country.

4. Can you tell me about your grandparents or great-grandparents?

This question invites your mom or grandma to share what they know — or what they’ve heard — about earlier generations. You might be surprised at the little anecdotes or nicknames they remember, or even the family legends that have passed down. Even if the stories seem small, they often lead to bigger discoveries in your family history search.

5. What lessons do you hope to pass down through our family?

Asking this brings the conversation into the present and future. What values, advice, or wisdom does your mom or grandma hold dear? This is a chance to hear about the principles that guided your family and that you might want to carry forward.

6. What was your home like growing up? Who lived there and what did it feel like?

Homes hold stories, too. This question invites memories of everyday life, like the sounds, smells, and people who made a house a home. Whether it was a bustling farmhouse, a small city apartment, or maybe they moved around a lot, these details create a vivid picture of the world your ancestors lived in.

7. Do you know where our family originally came from, or have you heard any stories about how they got here?

This is a key question for your family history search. It helps you connect with your roots and can uncover migration stories, reasons families left their homelands, or the challenges they faced. Sometimes these answers include fascinating details about travel, hardships, or dreams that motivated your ancestors.

8. Is there a recipe, craft, or skill you learned from someone in the family that you’ve always loved?

Family history isn’t just names and dates. It’s the tastes, sounds, and skills passed down through generations. This question brings those traditions into the spotlight, like maybe a favorite family recipe, a handmade craft, or a skill like gardening or sewing. These personal touches keep family heritage alive in everyday life.

9. If you could tell your younger self one piece of advice, what would it be?

This question is a gentle way to invite reflection and life lessons. It often leads to meaningful insights and sometimes unexpected stories about challenges faced or hard-won wisdom. And it’s a great way to deepen your connection through empathy.

10. Have you ever seen any old family documents, letters, or photos? What do you remember about them?

This final question opens the door to physical pieces of your family history. Whether it’s an old letter, a faded diary, or a box of photographs, these artifacts can be treasure troves for your family history search. And hearing your mom or grandma’s memories about these items adds depth and context you won’t find anywhere else.

Want to add more questions to your list? Take a look at this helpful guide. It includes prompts that help you learn more about your family’s history.

Photo by LaShawn Dobbs on Unsplash

How to Preserve These Stories for Future Generations

Once you’ve had this meaningful conversation, don’t let those stories slip away. You can record them (even a simple phone voice memo works) or take notes. Sharing the stories in a written journal or digital file helps keep them safe. I always recommend backing up recordings or notes in more than one place—trust me, it saves heartache later.

Another tip is to revisit these stories with your mom or grandma regularly. Memories can grow clearer or new ones surface when you give space and time. Plus, each visit builds a richer family history that you can pass on.

Need Help Organizing Family Stories? Here’s How I Can Help

I know family history search can feel overwhelming, especially when you’re juggling where to start and how to keep everything organized.

That’s where I come in. Whether you want someone to do the deep digging for you or prefer to work together while you learn the ropes, I offer flexible genealogy services tailored to your needs.

If you’re not sure how to begin, I invite you to book a free 20-minute discovery call with me. It’s a no-pressure way to chat about your goals and see how I can support you. 

For those who want me to take the lead, my done-for-you research packages offer deep dives into your family history with clear reports and actionable next steps.

If you want to be hands-on but with expert guidance, my done-with-you services are designed to help you learn how to research while we collaborate on your family history search.

This Mother’s Day, or any day really, reminds us how important it is to ask these questions. You never know what stories might surface—and what connections you’ll deepen. The past is waiting to be discovered, and your mom or grandma holds the key.

Remember, if you’d like help unlocking your family’s stories, I’m here for you.