One evening, a year into my marriage, I had a huge argument with my husband. It rattled me so much that I asked for some space and left home for a while.
Not wanting to be alone, I scrolled through my contacts and landed on one name: Siti.
She and I first met as colleagues, and even after we stopped working together, we kept in touch, exchanging the occasional life update, festive greeting, or random photo with the message: “Hey, this reminded me of you!”
The thing about us? Siti is almost three decades older than me.
I’m a 29-year-old millennial. Siti, in her late 50s, is Gen X, or those aged 45 to 60 in 2025.
Despite the age gap, we clicked right from the start. So when she came to keep me company that night, I knew I had called the right person.
We have what’s called an intergenerational friendship, a connection between people of different age groups, often with a gap of 10 years or more.
At a time when people dismiss each other as “backward boomers” (those 61-79 years old in 2025), “spoilt and entitled Gen Z” (aged 13-28), or “burnt-out strawberry millennials” (aged 29-44), my friendships with those from different generations matter deeply to me.
Having intergenerational friendships helps us remain humble and be more grounded. (Photo: iStock/CG Tan)
It’s not just that they give me “fresh perspectives” – any friendship across differences can do that. What makes intergenerational friendships unique is how much more humbling they are.
Being close to someone much older reminds me that even if my experience is new, I’m hardly the first to go through it, and I definitely won’t be the last.
After the row with my husband, Siti, who’d been through many spousal arguments herself, offered advice my then-25-year-old self couldn’t see.
She suggested why the fight might have happened, what was in my control, and most importantly, how to make amends. She gave me the space to be sad and incoherent while also sharing her own point of view as a mum in her 50s.
Her words stayed with me – besides helping me in that moment, I drew on them when it was my turn to support someone else.
I found myself in Siti’s shoes when a friend nearly a decade younger than me went through her first heartbreak. The boy she loved liked someone else – and she felt like the world had ended.
Even though I hadn’t lived her story, just as Siti hadn’t lived mine, the intergenerational relationships in my life remind me that others have walked ahead of me, and I, in turn, will walk ahead for someone else.
Beyond humility, intergenerational friendships also dismantle the stereotypes we have of each other. This comes through in both real life and pop culture.
In the movie The Intern, Anne Hathaway plays a millennial workaholic who learns to be more open from her new intern, played by Robert De Niro. (Photo: Warner Bros. Pictures)
My older friends once admitted they used to see millennials and Gen Zs as entitled or fragile. Through their friendship with me, however, they learnt that millennials can also be resilient and resourceful. And sometimes, “entitlement” just means better clarity on knowing what we want – something anyone of any age can relate to.
My teenage friends also see those in their late 20s – me – as already “settled”, “they’ve made it”, or even, out of touch. I share my many personal crises with them, hoping to show that uncertainty and self-discovery don’t end when one reaches 30.
And hey, being “out of touch” and embracing the joy of missing out on trends can be pretty cool, too.
It’s not just me. These stereotype-busting dynamics play out in other intergenerational friendships, too, albeit in “reel” life.
In the 2015 American movie The Intern, Anne Hathaway plays a workaholic millennial CEO alongside Robert De Niro’s 70-year-old widowed retiree. Their relationship begins with every generational cliche: An impatient youth versus an outdated elder.
As he interns in her company, both discover unexpected wisdom in the other and gradually understand the reasons behind their generational quirks.
The classic animated movie Up offers another example. At first, 78-year-old widower Carl Fredricksen and nine-year-old wilderness explorer Russell seem like caricatures of their ages: The grumpy old man and the young, naive kid.
But as they float away on their adventure, suspended by thousands of balloons, Carl eventually learns how to let go and lighten up from Russell, and the latter figures out how to be more courageous from Carl.
In the movie Up, Russell and Carl Fredricksen share an intergenerational friendship, where each learns to look beyond their stereotypes of the other. (Photo: Pixar)
These on-screen intergenerational friendships, and the real-life ones I have, prove the same point: Such friendships challenge stereotypes while providing a deeper and more nuanced understanding of each generation.
Intergenerational friendships are also special because of the differences.
When someone is in a different life stage, they don’t automatically understand your world. So you each have to explain, translate, meet halfway, or adjust your views to understand each other. These acts deepen the friendship.
I see this in my own life all the time, with friends like Siti, where all of us are open to sharing and stretching our understanding of each other.
I’ve shown older friends how to use social media apps, while they’ve introduced me to the slow, deliberate beauty of a vinyl player. With younger friends, I’ve helped them navigate the grief of leaving secondary school, while they keep me up to date on issues their generation cares about (or the latest lingo I can barely understand, no cap).
It’s in these exchanges, where none of us takes the other’s views for granted, and where we tease each other for playing straight into our stereotypes (me groaning about knee pain, them panicking about turning 20), that the friendship feels most alive.
Take Swedish climate activist Greta Thunberg, 22, who shares friendships with older people like Irish filmmaker and comedian Tadgh Hickey, who is in his 40s.
Their bond began with a shared passion for humanitarian causes, but it’s enriched by their differences: Hickey shows Thunberg how humour can be used effectively in activism, while she reminds him why youth-led movements feel so urgent.
With their different perspectives, they sharpen each other in ways they might not be able to if they’d only stayed among people their own age.
Another intergenerational friendship is that between 39-year-old American pop singer Lady Gaga and the late Grammy-award-winning singer Tony Bennett. Bennett was 59 years her senior and passed away in 2023.
On the surface, they couldn’t be more different. Gaga is known for her flamboyant and eccentric performances, while Bennett was the embodiment of timeless, old-school jazz. Yet they collaborated on two albums, and what struck me most was how their differences became a source of awe for each other.
Gaga has spoken about how moving it was to see Bennett battle Alzheimer’s disease, while Bennett often openly admired Gaga’s uninhibited way of expressing herself on stage. And since the jazz singer’s death, Gaga has continued to honour his legacy and their unique friendship during her performances.
The Gaga-Bennett friendship reminds me of my own intergenerational friendships, in which our differences become the foundation for respect, admiration, curiosity, and creativity.
They expand my views, make me curious, and remind me that growth in friendships rarely flows in just one direction. We are constantly teaching and learning from each other.
In a time when people so often critique one another, these friendships feel more crucial and meaningful than ever.
CNA Women is a section on CNA Lifestyle that seeks to inform, empower and inspire the modern woman. If you have women-related news, issues and ideas to share with us, email CNAWomen [at] mediacorp.com.sg (CNAWomen[at]mediacorp[dot]com[dot]sg).
Continue reading...
Not wanting to be alone, I scrolled through my contacts and landed on one name: Siti.
She and I first met as colleagues, and even after we stopped working together, we kept in touch, exchanging the occasional life update, festive greeting, or random photo with the message: “Hey, this reminded me of you!”
The thing about us? Siti is almost three decades older than me.
I’m a 29-year-old millennial. Siti, in her late 50s, is Gen X, or those aged 45 to 60 in 2025.
Despite the age gap, we clicked right from the start. So when she came to keep me company that night, I knew I had called the right person.
We have what’s called an intergenerational friendship, a connection between people of different age groups, often with a gap of 10 years or more.
"YOU’RE NOT THE ONLY ONE, WE’VE ALL BEEN THERE"
At a time when people dismiss each other as “backward boomers” (those 61-79 years old in 2025), “spoilt and entitled Gen Z” (aged 13-28), or “burnt-out strawberry millennials” (aged 29-44), my friendships with those from different generations matter deeply to me.
Having intergenerational friendships helps us remain humble and be more grounded. (Photo: iStock/CG Tan)
It’s not just that they give me “fresh perspectives” – any friendship across differences can do that. What makes intergenerational friendships unique is how much more humbling they are.
Being close to someone much older reminds me that even if my experience is new, I’m hardly the first to go through it, and I definitely won’t be the last.
After the row with my husband, Siti, who’d been through many spousal arguments herself, offered advice my then-25-year-old self couldn’t see.
She suggested why the fight might have happened, what was in my control, and most importantly, how to make amends. She gave me the space to be sad and incoherent while also sharing her own point of view as a mum in her 50s.
Her words stayed with me – besides helping me in that moment, I drew on them when it was my turn to support someone else.
I found myself in Siti’s shoes when a friend nearly a decade younger than me went through her first heartbreak. The boy she loved liked someone else – and she felt like the world had ended.
Even though I hadn’t lived her story, just as Siti hadn’t lived mine, the intergenerational relationships in my life remind me that others have walked ahead of me, and I, in turn, will walk ahead for someone else.
INTERGENERATIONAL FRIENDSHIPS BREAK DOWN STEREOTYPES
Beyond humility, intergenerational friendships also dismantle the stereotypes we have of each other. This comes through in both real life and pop culture.
In the movie The Intern, Anne Hathaway plays a millennial workaholic who learns to be more open from her new intern, played by Robert De Niro. (Photo: Warner Bros. Pictures)
My older friends once admitted they used to see millennials and Gen Zs as entitled or fragile. Through their friendship with me, however, they learnt that millennials can also be resilient and resourceful. And sometimes, “entitlement” just means better clarity on knowing what we want – something anyone of any age can relate to.
My teenage friends also see those in their late 20s – me – as already “settled”, “they’ve made it”, or even, out of touch. I share my many personal crises with them, hoping to show that uncertainty and self-discovery don’t end when one reaches 30.
And hey, being “out of touch” and embracing the joy of missing out on trends can be pretty cool, too.
It’s not just me. These stereotype-busting dynamics play out in other intergenerational friendships, too, albeit in “reel” life.
In the 2015 American movie The Intern, Anne Hathaway plays a workaholic millennial CEO alongside Robert De Niro’s 70-year-old widowed retiree. Their relationship begins with every generational cliche: An impatient youth versus an outdated elder.
As he interns in her company, both discover unexpected wisdom in the other and gradually understand the reasons behind their generational quirks.
The classic animated movie Up offers another example. At first, 78-year-old widower Carl Fredricksen and nine-year-old wilderness explorer Russell seem like caricatures of their ages: The grumpy old man and the young, naive kid.
But as they float away on their adventure, suspended by thousands of balloons, Carl eventually learns how to let go and lighten up from Russell, and the latter figures out how to be more courageous from Carl.
In the movie Up, Russell and Carl Fredricksen share an intergenerational friendship, where each learns to look beyond their stereotypes of the other. (Photo: Pixar)
These on-screen intergenerational friendships, and the real-life ones I have, prove the same point: Such friendships challenge stereotypes while providing a deeper and more nuanced understanding of each generation.
FRIENDSHIPS ARE STRONGER BECAUSE OF – NOT DESPITE – THE DIFFERENCES
Intergenerational friendships are also special because of the differences.
When someone is in a different life stage, they don’t automatically understand your world. So you each have to explain, translate, meet halfway, or adjust your views to understand each other. These acts deepen the friendship.
I see this in my own life all the time, with friends like Siti, where all of us are open to sharing and stretching our understanding of each other.
I’ve shown older friends how to use social media apps, while they’ve introduced me to the slow, deliberate beauty of a vinyl player. With younger friends, I’ve helped them navigate the grief of leaving secondary school, while they keep me up to date on issues their generation cares about (or the latest lingo I can barely understand, no cap).
It’s in these exchanges, where none of us takes the other’s views for granted, and where we tease each other for playing straight into our stereotypes (me groaning about knee pain, them panicking about turning 20), that the friendship feels most alive.
Take Swedish climate activist Greta Thunberg, 22, who shares friendships with older people like Irish filmmaker and comedian Tadgh Hickey, who is in his 40s.
Their bond began with a shared passion for humanitarian causes, but it’s enriched by their differences: Hickey shows Thunberg how humour can be used effectively in activism, while she reminds him why youth-led movements feel so urgent.
With their different perspectives, they sharpen each other in ways they might not be able to if they’d only stayed among people their own age.
Another intergenerational friendship is that between 39-year-old American pop singer Lady Gaga and the late Grammy-award-winning singer Tony Bennett. Bennett was 59 years her senior and passed away in 2023.
On the surface, they couldn’t be more different. Gaga is known for her flamboyant and eccentric performances, while Bennett was the embodiment of timeless, old-school jazz. Yet they collaborated on two albums, and what struck me most was how their differences became a source of awe for each other.
Gaga has spoken about how moving it was to see Bennett battle Alzheimer’s disease, while Bennett often openly admired Gaga’s uninhibited way of expressing herself on stage. And since the jazz singer’s death, Gaga has continued to honour his legacy and their unique friendship during her performances.
The Gaga-Bennett friendship reminds me of my own intergenerational friendships, in which our differences become the foundation for respect, admiration, curiosity, and creativity.
They expand my views, make me curious, and remind me that growth in friendships rarely flows in just one direction. We are constantly teaching and learning from each other.
In a time when people so often critique one another, these friendships feel more crucial and meaningful than ever.
CNA Women is a section on CNA Lifestyle that seeks to inform, empower and inspire the modern woman. If you have women-related news, issues and ideas to share with us, email CNAWomen [at] mediacorp.com.sg (CNAWomen[at]mediacorp[dot]com[dot]sg).
Continue reading...