10 Questions You'll Wish You Asked Your Parents Sooner

10 Questions You'll Wish You Asked Your Parents Sooner

Here's what I've learned from working with seniors: your parents have lived entire lives you know nothing about.

You know the highlight reel. You don't know the deleted scenes.

And those deleted scenes? They're the good stuff.

So I bought my mom and dad "Hear Your Story Books" on amazon. There's a mom & dad version.

Here's the mom version, https://amzn.to/45c5kI6

Stop waiting for the "right time" to ask these questions. The right time is now.

1. What's the biggest risk you ever took?

Not "tell me about a time you were brave." That's a job interview question.

Biggest risk cuts straight to it. The business that failed. The move across the country. The person they said yes to.

You'll learn what mattered enough to bet on.

2. What did Saturday mornings look like when you were 10?

Specific beats general. Always.

Don't ask about their childhood. Ask about Saturday mornings. The routine. The smells. Who was there.

Details unlock memory. Memory unlocks stories.

3. Who broke your heart before Mom/Dad?

Everyone has a first love story. Most people never ask.

You think you know your parents' romance. You know chapter 10. You're missing chapters 1-9.

4. What's something you're really good at that nobody knows about?

Hidden talents are everywhere at The Joy. One resident was a semi-pro bowler. Another spoke four languages. Another built furniture that's still in their grandkids' homes.

Their families had no idea.

Ask this question. Then ask them to show you.

5. What job did you have that you never told us about?

People work weird jobs before they land the "real" one.

Your dad probably wasn't born an accountant. Your mom didn't emerge from the womb as an elementary school teacher.

The in-between jobs are always interesting.

6. What's the worst fight you and Mom/Dad ever had?

This one makes people uncomfortable. Ask it anyway.

Perfect marriages don't exist. Every couple has a moment they almost didn't make it.

Understanding how they got through it teaches you how relationships actually work.

7. If you could relive one day exactly as it happened, which day would you pick?

Not change it. Relive it.

The birth of a child. A perfect afternoon. A conversation with someone who's gone.

This question reveals what they value most.

8. What's something you believed at 30 that you know now was completely wrong?

Wisdom isn't just what you learn. It's what you unlearn.

Your parents spent decades figuring out what matters. They can save you time.

9. What's a family story that nobody tells anymore?

Every family has legends that fade. The cousin who did something crazy. The move that changed everything. The tragedy that shaped the next generation.

Ask before the storyteller is gone.

10. Is there something you've been waiting for the right moment to tell me?

Open-ended. No pressure. Just space.

You'd be surprised what people say when you give them permission.

Here's How to Actually Use These

Don't make it an event. No sit-down interviews with a notebook.

Ask one question on a drive. Another over coffee. Work them into regular conversation.

Record the answers. Voice memo on your phone. You think you'll remember. You won't.

Follow the rabbit holes. If they mention a name you don't know, ask about that person. If they reference a place, ask what it was like.

The best stories live in the tangents.