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17 July 2021

Twenty-one questions to ask your parents while they are alive and you still can.

Jairek Robbins

We don’t realize how quickly life can slip away … Do not let time get away from you; start asking these questions and record the answers for your memories and future generations.

A conversation each week over a cup of tea or even via zoom is a great way to deepen a relationship with someone special in your life.

Looking back, it was one of the best things I consistently did while my mother was still alive. We’d talk a few times each week, and I’d always have an interesting question to ask her about life, love, family, parenting…etc.

Sometimes it was about the answer; sometimes, it was just about taking a moment to be deeply curious about what someone you love has to share and making them feel special while they share it with you.

Here are a few questions to get you started:

1. What is the best thing about being my (grand-) parent? The hardest part? Your favorite part?

2. What is the most exciting thing you have ever done? What was the best part about it?

3. When were you the happiest and why? Sometimes just taking a moment to be deeply curious about someone can bring back beautiful memories for them and allow them to relive those moments again – with you.

3. What’s the best lesson you’ve learned in your life?

5. What was the most difficult decision you ever made, and why?

6. How did you make that decision? Perhaps learn from the process they used to create a tough decision to see how well it works for you when making similar decisions.

7. What memorable things did you do as a child to make people laugh? How did it make you feel inside when they laughed with you because of something funny or unexpected that you said or did?

8. If we could visit one place in the world, what would we see together?

9. What do you most regret in your life to date? How did you overcome it, or what are you doing about it now? Perhaps learn from their experience to avoid similar regrets of your own …

10. What was the proudest moment in your life? Why was it so special?

11. Have you ever had a conversation with someone who made you feel like a million dollars, and what was it about the way they spoke to you or their words that made them so memorable?

12. What was the best compliment you ever received, and why did it feel so good to receive it?

13. What was the most adventurous thing you ever did?

14. What are three of the most important things I could know about you growing up? For example, did you participate in sports, and if so – what was your best sport and why? What were your favorite cartoon characters as a child? What’s the funniest thing that happened to you while walking home from school (or driving back from a date)?

15. What is one book that helped shape the way you see the world?

16. If you could go back in time, what advice would you give to your teen self or your young adult self?

17. Who are three of your favorite people (living), and why do they make it on your list?

18. What is your idea of a perfect day? A nearly perfect day, where things went well or the way they should have gone? Perhaps learn from their experience to make your days more special or memorable as a result.

19. What do you believe is the best way to build solid and lasting relationships in general? What are the ingredients of a long-term loving relationship between two people or among many people that last for generations?

20. If you could go back now with all of your knowledge, understanding, and wisdom gained from experience now, what would you do the same, and what would you do differently?

21. What legacy and lessons would you like to pass down to your children (or grandchildren) and why?

I hope you enjoyed the list of 21 questions to ask your parents or grandparents while they are alive, and you still can. These types of conversations can help capture some memories that will last a lifetime.

Ensure that if there is anything on this list that speaks deeply to your heart (or theirs), please do not hesitate to share!

Your words could make all the difference for someone who needs encouragement right now.

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