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The 20 questions you should ask your grandparents: ‘It makes for tears of laughter and grief, a sense of connectedness’

Fortune Well July 10, 2023


The 20 questions you should ask your grandparents: ‘It makes for tears of laughter and grief, a sense of connectedness’

In the 1950s, when he was walking through the Khan el-Khalili bazaar in the center of Cairo—where the scent of the fluorescent-colored spices of turmeric and saffron swirled through the air—someone caught his eye. 

“That minute I saw her,” my then 90-year-old grandpa told me in the fall of 2020 at his house in Troy, Mich. But right when he did, he lost her in the sea of people. 

Months later, that same girl was looking through the vitrines in Tahrir Square when my grandpa saw her again before she hopped on a bus. 

Yes, my grandpa followed her on that bus before knocking on her door to politely ask her brother if it would be okay to introduce himself (back then, this was a truly romantic gesture).  

He kept his eyes on “this girl,” as he described her in his deep Arabic accent. He was mesmerized by her. And “this girl” became my Taita—Arabic for grandmother. 

This story has stayed with me since my grandfather’s passing later that same year. I’d been told the story of how he fell in love when I was much younger, but hearing it again curled next to my grandpa just a few years ago left me with a warm sense of peace and hope that is hard to put into words. I’m grateful I get to hold his stories close. It helps me understand his life far before I came into it and brings color to the history of his immigrating with my dad to the U.S. in 1968. 

His stories left me longing for more, so I could laugh at his lengthy descriptions of seemingly irrelevant details or admire his smile, remembering my Taita just one more time. 

As the days go by, it can feel like time is against you. The phone call to your grandfather ends up at the bottom of the list. But connecting intergenerationally through the power of storytelling serves us and our loved ones. 

It sure served me and everyone who heard my grandfather’s stories. It helped that he was always eager to share.


Storytelling heals the soul 

Many people struggled with connection before the pandemic and continue to do so afterward. The isolation only exacerbated the longing for genuine companionship, as seniors face a loneliness epidemic and young adults struggle to cultivate meaningful friendships in virtual workplaces. 

Loneliness is a serious public health issue and increases people’s risk for dementia, heart problems, and early death. 

“One of the protective factors in community health and well-being is social cohesion and connectedness,” Cío Hernández, Ph.D., a licensed marriage and family therapist, tells Fortune. “Safety and connection are vital for us as a species.”

Martin Seligman, Ph.D., who served as president of the American Psychological Association and championed research on positive psychology, founded the theory of well-being, which includes five main pillars, including relationships. 

“The experiences that contribute to well-being are often amplified through our relationships, for example, great joy, meaning, laughter, a feeling of belonging, and pride in accomplishment,” according to the theory’s web page on positive psychology at the University of Pennsylvania. “Connections to others can give life purpose and meaning.”

One way to prioritize connection is closer to us than we realize. It can be within our own families. 


Where do I start? 

Make connecting with older family members routine, if accessible to you. Start by asking questions and listening intently to learn more. 

“Make asking questions of our elders and our children easy by talking early and often about everything,” Hernández says. “It makes for tears of laughter and grief, a sense of connectedness, and the path for knowledge transfer to take into the future.”

If you feel like you’ve dropped the ball, don’t panic. You’re not alone, and it’s never too late. Even starting with simple texts like “I thought of you…” when something reminds you of them, or “sending you a hug,” Hernández says, can foster a relationship. 

“That acknowledgment…whether they reply or not has a lasting impact,” she says. 

After starting slowly, you can offer to connect online or in person through a shared activity or game and get to know each other in moments of pause. 

“Make their world important to you,” Hernández says. “When you make their worlds important to you, it’s a lot easier for you to start popping in some of the things that you want them to know about your life and the things that you’ve lived through.” 

So what questions do you ask a grandparent? 


Questions children can ask a grandparent

Parents can help facilitate conversations with grandparents by encouraging question-asking and even modeling asking questions. 

Children can ask their grandparents to “tell them everything” about a book, movie, story, or event, Hernández says. 


Questions teens can ask a grandparent

Teens begin to explore what they like and who they are, and they face struggles when it comes to relationships, school, and the future, Hernández says. 

“This is a great time to ask grandparents what music they listened to, what were the hardest parts of being a teen when they were young, who supported them, and how they got through difficult times,” she says. “Teens looking for a sense of belonging can find solace in hearing about their ancestors who may have passed their traits to them.”


  • What kind of music do you like? What hobbies did you enjoy at my age?
  • What were the most challenging parts of being a teen? 
  • Who supported you when you were a teen? 
  • How did you get through some of your difficult times at my age? 
  • What was school like for you? 
  • Who were some of your best friends growing up? 
  • What were your grandparents and parents like? 
Questions to ask a grandparent as a young adult 

Young adults face more complex life choices around careers, long-term relationships, and moving. It can help to know how older relatives navigated the same difficult choices and changes. 

“Young adults are figuring out what partners will be right for them,” Hernández says. “This can be such a special time to learn about what love was like for our grandparents.” 

While not everything needs to be heavy, practicing vulnerability through asking questions and storytelling can help us navigate our journeys. 

“People have survived all sorts of trauma, and although there can be some shame in sharing that, it’s also what preserves our history and shows how strong we are in our family,” she says. 


  • How did people find long-lasting friendships and relationships when you were my age? 
  • What did love look like for you at my age? 
  • How did you get through your first heartbreak? 
  • How did you gain confidence in your school and career decisions? 
  • How did you manage money and finances at my age?
  • How did you choose your career? Did you end up staying in the job you thought you would have? 
  • What was the scariest thing you ever did? 


Questions to ask a grandparent as a working parent 

Working parents, those sandwiched between an elder relative and their own children, face a host of challenges when it comes to caregiving. It can be hard to focus on wholesome moments when practical life decisions loom. 

“Many grandparents and elder relatives in this phase of life may grieve more often as abilities start to change, friends and loved ones start to pass on, and life roles start to change,” she says. “Although I hope the process of knowledge transfer to our future generations starts at younger phases, urgency becomes more a matter of time.”

People in this stage can still ask general and practical questions that shed light on how this grandparent wants to live out their life. 

“Working or parenting adults may want to seek even more precious opportunities to connect with their elders. Ask them about their values related to money, success, business, legacy, and what makes them feel proud of themselves,” she says. “Questions like end-of-life views, perspectives, and wishes become important both to teach children how to approach the topic of death, but as a practical dynamic for when the inevitable arrives.” 


  • How would you ideally live out the rest of your life? 
  • What do you wish you knew when you were younger (about love, a career, etc.)? 
  • How do you want the generations after us to remember you? 
  • When do you feel most calm and alive? 
  • What have you learned about success and the workplace? 
  • When were you most proud of yourself? 

Reaching out and not knowing how a relationship may evolve can be scary. But beginning slowly, over a shared interest, before asking deeper questions can make it easier—and ultimately, incredibly rewarding. 

Bottom line? “Go and bug your grandparents and relatives, tell them how important they are, not just for you, but so the future generations can know about their family,” Hernández says. 

For me, my grandfather’s sense of humor, dedication to family, determination, and ability to trust his gut will be passed down because of his stories—even if jumping on a bus when you’re lovestruck may not be the best advice. 

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