Meaningful Questions to Ask Aging Parents About Their Life, Wishes and Stories
There are questions we ask our parents because we need information.
And there are questions we ask because someday we may desperately wish we had.
A few weeks ago, I wrote about the practical conversations I believe adult children should have with aging parents: wills, powers of attorney, finances, healthcare wishes and all the details families often don't discover until they're urgently needed.
Those conversations can be awkward.
For me, they were still the easy ones.
The harder conversation had nothing to do with documents.
It was about what I wanted my parents to hear from me, what I wanted to hear from them and what I didn't want to leave unsaid.
I did eventually have those conversations with both of my parents.
I am grateful, and honestly relieved, that I did.
I don't put much stock in regrets.
That's one I'm glad I don't have to live with.
There Isn't One Big Conversation
I used to imagine this as a single important talk.
Sit down.
Say everything.
Ask everything.
Walk away knowing you did it.
It wasn't like that.
With my dad, I had a series of conversations, partly because they were difficult enough that I kept cutting them short.
I'd leave thinking:
Okay. We covered it.
Then that night I'd remember something else I had wanted to say.
So I'd go back.
Looking back, I think that's a better way to think about these conversations anyway.
You don't need one perfect moment.
You need to start.
For me, most of what mattered fell into three categories:
Gratitude. Stories. Questions.
1. Gratitude: Tell Them What They Meant to You
This sounds obvious.
It isn't always easy.
We assume people know.
Of course Dad knows I'm grateful.
Of course Mom knows what she meant to the family.
Maybe they do.
I still wanted to say it.
With my mom, I found that direct emotion had limits. She appreciated the questions, but she wasn't interested in sitting around having the dramatic conversation I might have imagined.
Tears came more easily than laughter, and neither of us seemed to enjoy that.
So I learned to work within the boundaries she gave me.
I told her I was grateful.
I told her what she meant to my kids.
I told her what she meant to my wife, who was in many ways my mother's favorite person.
My mom once looked at me and asked:
“How on earth did you get somebody so wonderful?”
Fair question.
She would often change the subject when I got too direct.
But I could tell she heard me.
That was enough.
Things You Might Want to Say
You don't need an eloquent speech.
Try:
- Thank you for...
- One thing you taught me that I still use is...
- I understand something you did for me now that I didn't understand then
- One of the things I admire most about you is...
- My kids know this about you because...
- Something I hope I carry forward from you is...
- One of my favorite memories with you is...
Specific usually beats grand.
2. Stories: Ask for the Version Only They Know
With my dad, stories were easier.
I would bring up things from childhood, partly to refresh his memory and partly because I genuinely wanted his version of events.
Some involved me getting into trouble as a teenager and Dad having to rescue me.
Those were particularly successful.
My goal with him was often simple:
Get him laughing.
When I managed that, we both felt better.
The stories didn't have to be historically significant.
They mattered because he was the only person who could tell me what those moments looked like from where he was standing.
Questions to Ask Aging Parents About Their Life
If you aren't sure what to ask, start with stories.
Childhood
- What were you like as a kid?
- What did you get in trouble for?
- Who were you closest to growing up?
- What did your parents worry about?
- What did your family do for fun?
- What did holidays look like in your house?
- What was your neighborhood like?
- What did you think you'd be when you grew up?
Young Adulthood
- What were you most unsure about in your 20s?
- What was your first real job?
- What did you spend your first paycheck on?
- Who were your closest friends?
- What did you think adulthood would be like?
- Was there a decision that changed the direction of your life?
- Is there somewhere you lived that you still miss?
Love and Family
- What do you remember about meeting Mom or Dad?
- What first attracted you to them?
- When did you know the relationship was serious?
- What surprised you most about becoming a parent?
- What did you worry about when I was growing up?
- Was there anything about parenting that you think you got completely wrong?
- What were some of your happiest family moments?
Those questions can go places you don't expect.
Let them.
3. Ask About the Stories You Think You Already Know
This may be the most underrated category.
You probably have family stories you've heard 100 times.
Ask again.
But change the question.
Instead of:
“Tell me about the time you moved to Chicago.”
ask:
“Were you scared when you moved?”
Instead of:
“Tell me how you met Mom.”
ask:
“What did you think of her the first night?”
Instead of:
“Why did you leave that job?”
ask:
“Did you know at the time that it was the right decision?”
Facts are useful.
Perspective is usually what disappears.
Questions About Who They Became
Try asking:
- What are you most proud of?
- What do you think you were best at?
- What did you care about too much when you were younger?
- What matters less to you now?
- What matters more?
- Who changed you?
- Is there anyone you wish you had thanked?
- What is something you changed your mind about?
- What was harder than people realized?
- When were you happiest?
- What do you wish you had worried about less?
These aren't questions about aging.
They're questions about a life.
Questions About Family History
There are also practical stories worth preserving.
Ask:
- Where did our grandparents grow up?
- What were they like?
- What family stories do you remember hearing?
- Which relatives were you closest to?
- Are there traditions you hope the family continues?
- Are there recipes we should know?
- Are there photographs whose stories no one else knows?
- Are there family names or places we should remember?
- Are there stories about relatives that aren't written anywhere?
Pull out photographs while you're talking.
Names and places have a way of disappearing from family history surprisingly quickly once the person who remembers them is gone.
Questions About What Matters Now
Not every meaningful question has to be about the past.
Ask:
- What makes a good day for you now?
- What do you look forward to?
- What makes you feel most like yourself?
- What do you wish people understood about you?
- Is there something you still want to do?
- Who do you most enjoy spending time with?
- What do you want more of?
- What do you want less of?
- Is there something the family does for you that you wish we'd stop doing?
- What would make life easier right now?
These answers may actually change how you show up for someone today.
When a Parent Has Memory Loss
My mother lived in memory care.
Her memory could still amaze me.
She could sometimes fill in the blanks on old stories about family and friends when I wasn't expecting it.
She'd get misty-eyed.
Then she'd want another story.
At other times, the conversation simply wasn't going where I wanted it to go.
That's important.
If a parent has dementia or another form of memory loss, don't treat the conversation like a test.
You're not trying to determine whether they can correctly answer 30 questions.
You're spending time together.
An old photograph, song, place or familiar story may open a conversation.
If it doesn't, move on.
The goal is connection, not a complete oral history.
Don't Demand the Emotional Response You Imagined
This was something I had to learn with my mother.
I wanted certain conversations to feel meaningful.
She didn't always want to participate in my version of meaningful.
Sometimes she changed the subject.
Sometimes she cried.
Sometimes humor worked.
Sometimes it didn't.
Eventually, I understood that the conversation had to happen in a way she could receive, not simply in the way I wanted to deliver it.
That's true even without dementia.
Your parent may:
- Make a joke
- Change the subject
- Give you a three-word answer
- Tell you the same story again
- Get uncomfortable
- Ask why you're suddenly being so serious
Let the conversation be theirs too.
What If You Don't Know What to Say?
There's a moment in the medical drama The Pitt that resonated with a lot of viewers.
The show references four simple statements associated with palliative-care physician Ira Byock's work and on the show drawn from a Hawaiian practice called ho'oponopono:
- I love you
- Thank you
- I forgive you
- Please forgive me
You don't need to use all four.
You may not need any of them.
But I understand why the idea stuck with people.
Sometimes we are searching for the perfect speech when the important things are remarkably short.
“I love you.”
“Thank you.”
“I remember.”
“I'm glad you're my dad.”
Those may be enough.
Don't Wait for the Perfect Moment
I didn't get all of this right.
I waited too long for some things.
I didn't ask every question.
I didn't say everything as elegantly as I might have wanted.
And some conversations didn't end with anything resembling the emotional resolution you see in movies.
That's real life.
But waiting for:
- The perfect moment
- The perfect words
- The perfect response
- A day when nobody feels awkward
can become another way of not having the conversation at all.
Start somewhere.
COVID Taught Me How Quickly the Opportunity Can Change
My mother's decline accelerated during COVID.
She was largely confined to her room, and visitors could only see her outdoors.
That worked when the weather cooperated.
Once it got cold, she didn't want to be wheeled outside just to see us.
FaceTime, even with a caregiver trying to help, was a disaster.
I was relieved that I had already had many of the conversations I wanted to have.
Not all of them.
Enough of them.
I had told her what she meant to me.
I had told her what she meant to my children.
I had told her what she meant to my wife.
She changed the subject plenty of times.
But I believe she heard it.
A Few Questions Worth Asking While You Can
If you want someplace simple to start, choose five:
- What's one of your happiest memories?
- What were you like before I knew you?
- What are you most proud of?
- What do you wish you'd worried about less?
- What did your parents teach you?
- What do you remember about becoming a parent?
- What is something you've changed your mind about?
- Who had the biggest influence on your life?
- What family story should we make sure doesn't disappear?
- What makes you happiest now?
- Is there something you still want to do?
- Is there anything you wish I'd asked you?
- Is there something you want your grandchildren to know?
- What do you hope our family keeps doing after you're gone?
- Is there anything you want me to know that we've never talked about?
You don't need all 15.
One good question can be enough.
The Practical Conversation Matters Too
If you haven't yet talked about your parent's legal documents, finances, healthcare wishes, living preferences and other practical planning, start there too.
Our companion guide, Questions to Ask Aging Parents About Their Future, includes a practical checklist covering the information families are often grateful to have before they urgently need it.
The two conversations are different.
I think families need both.
There Is More to Say Than We Usually Think
One small thing I learned caring for my parents is that easier daily routines leave more room for the parts of life that actually matter.
That's part of why we eventually created Joe & Bella.
Getting dressed shouldn't consume the energy someone could be spending talking, laughing, remembering or simply being together.
But this article isn't really about clothes.
It's about saying the things you want someone to hear.
Ask the question.
Tell the story.
Say thank you.
Make them laugh if they'll let you.
And don't worry quite so much about whether you did the conversation perfectly.
The important part is that you had it.
About Peter Zollo
After a decade caring for both of his parents, Peter Zollo co-founded Joe & Bella to make daily life easier and more dignified for older adults and the people who care for them.
Peter co-led three studies for AARP on longevity. As founder and former CEO of Teenage Research Unlimited, he authored three books and spent his career studying how people think and change across life stages.
At Joe & Bella, that lifetime of generational insight meets the daily realities of aging, caregiving and what it means to stay yourself.