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Questions You'll Wish You Asked

The memories of our seniors are akin to treasure.

They are the keepers of sacred family history, touching personal stories, and a perspective of cultural events unique only to them.

Why not commit to asking a beloved senior about those valuable memories, while also creating more purpose and connection with them in the present?

The Questions You’ll Wish You Asked journaling book series was designed to do exactly that.

A project born from grief and love, creator Melissa Pennel shares the journey of creating these series in her words below:

“In the span of only a few years I lost a large chunk of my family: my last three grandparents passed away, and my mom (who raised me as a single parent) unexpectedly died of a heart attack. I was left in shock at the empty space where my family used to be.

Though I shared endless conversations with these loved ones while they were alive, there were so many questions I had once they were gone—things I wish I asked, answers I didn’t remember, and information that I craved.

Who were they before I knew them?

How did their story shape mine?

What had they wanted me to know?

Since that period of deep loss, I’ve often encouraged others to ask their loved ones the questions they might someday have. It was from this place that the Questions you’ll Wish You Asked series was born.”

Following this period of grief, Melissa designed a journal unique to every family relationship, and each include prompts about a host of topics.

Some relate to recording important family history, such as:

What did our ancestors do for work?

What did you learn from your mother and father?

How do you think your parents’ upbringing shaped how they raised you?

Other questions were designed to prompt joyful memories and light hearted stories, such as:

Do you remember your first date?

What was your first job? Did you like it?

Do you have an embarrassing moment that stands out? How did you recover?

Still more questions are designed to elicit thoughtful reflection about the pair sharing the journal, such as:

What are you most proud of me for?

What should I do when I’m confused and don’t know what to do?

If you could choose your last words to me, what would they be?

For those who might struggle to remember or who want to keep things light, there are also simple and easy to answer questions:

What are your favorite books and movies?

What is your favorite meal?

What is something that always makes you smile?

Though the journals are designed to be written in by those answering, some choose to transcribe answers for an older family member, or let the questions inspire meaningful conversation at the dinner table. Regardless of how the conversation is had, sharing memories is a gift for both the answerer and the recipient; the simple act of reflecting on precious memories can conjure joy, provide purpose, and sharpen cognition.

After all, our seniors are the beloved keepers of not just our collective story, but their own unique and valuable experiences. Asking them the right questions can remind them of their own value, spark more questions you might have about their life, and also create a keepsake of love that will be treasured for generations to come.

Are you asking the questions you’ll wish you had? It’s never too late to start.

Find all of the Questions You’ll Wish You Asked journals here.

And if you're looking for in home care in San Francisco or the nearby areas, contact Alegre Home Care, one of the top home care agencies in San Francisco and the nearby areas today!

About the Author

Melissa Pennel is a writer, mother, and coach living in Northern California. She is the author of the Questions You’ll Wish You Asked series of keepsake journals, a collection that stemmed from the grief of unexpectedly losing her family before asking important questions. Find more of Melissa’s writing by subscribing to her blog or visiting

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