Senior Resources » 20 Meaningful Questions That Will Bring You Closer to Your Elderly Loved Ones

20 Meaningful Questions That Will Bring You Closer to Your Elderly Loved Ones

Asain senior in a wheelchair, looking up and talking to a woman loved one or caregiver

Almost six decades ago the Pulitzer Prize-winning psychologist and gerontologist Dr. Robert N. Butler began studies on the relationship between elderly wellness and their ability to both reflect on their lives in a sort of life review, and the value of being able to share these stories and insights with a valued listener. His studies at the time proved the great benefit for the senior population both in reflecting on their life story and in having their stories heard as well as affirmed. As a physician in the United States, Dr. Butler also noted in his studies the unfortunate observation that as a society often the stories shared by our elderly were being can be cast off as unimportant or worse, as senile musings. 


Studies from Blue Zone areas that boast vital senior populations, as well as larger than normal centenarians, have pinpointed that one of the key factors of longevity in these areas can be attributed to senior residents possessing a strong sense of purpose and value within their communities.   

Current common wisdom notes that actively listening to another human being has a multitude of benefits for both parties. This may be particularly noticeable as we ask meaningful questions of our elderly loved ones seeking to connect more deeply with them, and giving them a loving space in which to reminisce. 


Create a Loving Environment for Sharing 

father and son outside hugging

Senior loved ones may not be quick to share if they have not previously had ongoing opportunities to tell their stories and share their thoughts or questions in past communications with you and/or other caregivers and family members. 

As you seek to build a genuine rapport in your conversation with an elderly loved one, start with a simple principle of Love-Learn-Laugh. A Love mindset comes with a commitment to consistent interaction with your loved one. Showing up regularly and conferring value upon your elder builds a platform of trust. Even a simple phone call can help to build this consistency. Asking open-ended questions, perhaps one or two at each interaction gives them permission to share in bits and pieces. Be careful not to correct, but rather seek in as much as possible to affirm, and or clarify by asking another question. This indicates to your loved one that you are interested in them and want to Learn. 

As an elder begins to feel that you are both interested and want to gain either from their wisdom gained through life, or from their knowledge of family and history, they will warm and open to reminiscing freely, allowing for a deeper connection between you. 

Finally, make space for tender laughter, always ensuring that humor is shared and in no way diminishes the story or value of your loved one. Founder of Care Hop, Michael Lu encourages, “A shared laugh can build closeness with your elderly loved one.” 


Below are 20 questions that you can use as a springboard for beginning rich communication between you and your elderly loved one. 

Questions to Encourage Sharing of Your Loved One’s Legacy

elderly loved one sharing old photos with granddaughter

1. I would love to learn more about your family history…

Tell me more about your parents and your favorite things about growing up in your family. What is your best memory with your mom and dad? Did they tell you about their childhood? Where they lived or how they ended up married? Or about their parents? Do you have any funny or silly stories about your family? 

2. I am so interested in our heritage…

Can you tell me more about our culture? What were your favorite foods growing up? Was there anything that your family cooked that was especially a family favorite, or that was passed down through the generations? Did you help prepare those family favorites? What was your favorite holiday tradition? Did you struggle with your heritage in any way? 

3. What is your earliest memory?

This could be something simple, or a shadow of a memory, and could be difficult or delight-filled. Be sure to let the story unfold and ask tender affirming follow-up questions.

4. Tell me about your siblings…

How did your childhood impact how you raised your children? Did any of your siblings remind you of your parents or perhaps of your own children?


5. What was it like growing up in ___________?

What was school like? What was your favorite subject?  What did you do for fun? Who were your friends? Did you do chores? Play sports? Have pets? 

6. I love the story about how you fell in love, can you tell me that story again?

This question can open up many emotions, especially if love has been lost. Be prepared to listen with empathy, and ask gentle questions to let your elderly loved one walk through all the emotions of a past courtship and/or loss of a loved one. Also, be open to the possibility that your loved one may have had more than one love, and may want to tell these stories as well. Opening the gateway to connection and reminiscing requires that the listener be open to the fullness of a life abundant with years and stories. 

Questions to Understand Your Elder Loved One More Deeply

hospice hands

7. How did you choose your career?

Did you enjoy the work you did or feel a sense of accomplishment? What was the most difficult experience you encountered in your work life? What was your greatest gain? 

8. Will you tell me more about what you believe?

What are your personal thoughts on faith and what is important in life and worthy of your time? How has that philosophy made your life better or helped you know how you wanted to live?  

9. What do you consider the most courageous thing you’ve ever done in your life?

Or, what do you consider the hardest thing you’ve ever done?

10. What is your favorite memory?

Is there anything that helps you bring that memory to mind? What about this memory makes it your favorite?

11. Who influenced you the most?

A teacher or mentor? A dear friend or family member? How about someone famous?

12. What world events have impacted you the most?

Or, what places have you traveled to that have impacted your life? How do you think they changed your daily life? 


Questions to Connect You More Personally to Your Elder Loved One

hugging and smiling woman with senior mom

13. In what ways do you think I am similar or different to you?

Do you think we have any of the same shared dreams, habits, struggles, or physical characteristics? It is important with this question to avoid refuting and engage in deep listening and where possible affirmation. 

14. What insights can you share with me?

What insights can you share with me about living (parenting, grandparenting, or any area that you choose) that may help or encourage me as I continue throughout my life?

15. What is your favorite personal memory with me?

What memories do you still hope that we might be able to share? How can I help build that together with you?

Questions That Build Your Ability to Be a Support

teen helping grandma

Open-ended empathic questions invite your elderly loved one to answer need or like-based queries without feeling that they are awkwardly asking for help or revealing hidden fears and weakness. As a good listener, it is imperative that even when trying to determine how to best give care, or perhaps bring added delight and value to the life of an older person, we frame our questions in a manner that honors and builds long-term trust and connection. 

16. I sometimes struggle with ___________.

Do you ever find that you struggle with this as well?

17. I really enjoy ____________.

What do you enjoy?

Questions Just for Fun 

daughter and mother

Author Claire Samuels encourages caretakers and family members in the art of engaging elders in reminiscing as a way to connect more intimately. She suggests these fun questions to get the conversation rolling. 

18. Which invention from your lifetime amazed you the most?

19. What is the weirdest fad you remember?

How about expressions or slang? Crazy hairstyles or clothing choices?


20. What was your favorite movie or TV show when you were younger?

Favorite book? Favorite comic strip? 


Other fun questions might include favorite childhood or current games, silly jokes, or harmless childhood pranks. Conversations that evoke laughter offer the gift of creating a shared bank of joy-filled moments, with the added benefit of strengthening and even healing relationships.  

Meaningful Questions That Will Bring You Closer to Your Elderly Loved Ones

Asain senior in a wheelchair, looking up and talking to a woman loved one or caregiver

Taking the time to create consistent opportunities in which you share thoughtful questions within a loving environment, can offer both the listener and elderly loved one untold depths of understanding and personal connection. For your loved one they may experience a wealth of renewed self-esteem and contentment and satisfaction with life. There is a certain delight and beauty for people of all ages in the process of reflecting and reminiscing on their own life. This truth is especially poignant when good communication causes the history of a life to be seen as both valued and worthy of being shared. As one ancient proverb encourages, “…the gray hair of experience is the splendor of the old.” 

Happy listening! 

Originally published February 07, 2024


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