When Your Best Friend Is Younger Than Your Daughter

Photo: Camille Tokerud/Getty Images

A friend of mine jokes that I accumulate older women with weekend homes the way other people do spare change. I don’t actively seek them out (and I certainly don’t treat them like spare change), but I’m not immune to their charms. I grew up with two sisters who are 10 and 14 years older than me. By the time I was in high school, they felt less like siblings and more like a pair of super-cool aunts. If one bought me peach-flavored wine coolers for my first senior party, the other picked me up afterwards. They had style in spades and great taste in music, both of which they tried diligently to pass on to me in the form of hand-me-downs and mixtapes, with varying degrees of success. They offered guidance with the perspective of age and I took it gladly, with none of the teenage skepticism I typically reserved for anyone older than me.

Because they were my sisters, I saw them intimately despite the distance between our ages: as “adults” in their thirties who had professional success but still stayed out dancing until all hours of the night, spent money with equal responsibility and abandon, and, to put it most bluntly, took their sweet time growing up. They were grown-ups who managed to be as real and three-dimensional to me as my friends my age. I couldn’t wait to be them.

Now, in my early thirties, I’ve found myself with a number of close friends who were well on their way to graduating high school by the time I was born. Brandon is a former boss 17 years my senior. We surf together in Montauk. Sarah Gray is my older sister’s age and lives upstate. We spend winter weekends in bed together reading gossip magazines and summer ones drinking rose at the local swimming hole. For my friend Julianna’s 45th birthday this past November, a group of us ranging in age from 29 to 52 spent a long weekend in South Carolina. The only time age came up was during a conversation about skin serums.

I may have reason to be more comfortable with a friendship age gap than others, but I am certainly not alone. Take, for example, Amanda Keiser, 33, and Ruth Abram, 71, who met through their husbands — both lawyers — last year. Their first “date” was a long weekend trip to Ruth’s home upstate, an admittedly daunting proposition for two women almost 40 years apart in age. “We were both sort of like, ‘Oh, a whole weekend, huh?’” Amanda recalls. “But right after they picked us up from the train station, Ruth started talking about a séance she went to. That’s when I realized, okay, this is going to be cool.”

Cross-generational friendships are more common in women than men, but only because friendships are, too. Male friendships tend to revolve around activities, while women prioritize emotional connection. So in order to foster an intergenerational friendship, not only do men have to find a common activity to do together, they have to make sure that it’s also open to a wide range of ages. Women can simply catch up over coffee.

Men also tend to have fewer friends to begin with and are worse at maintaining the ones they do. Women struggle with friendship maintenance in our late 20s and 30s (especially working mothers) as studies show that’s when most of our time and energy is spent on our careers and family, but make up for it by redoubling our efforts in our 40s and 50s. It’s a literal life-stage, The Wall Street Journal reports, in which women begin to “plan the next chapter of their lives [and] turn to friends for guidance and empathy.”

Feminist cultural critic Joan Morgan, who counts 33-year-old professor Dr. Treva Lindsay amongst her closest friends, thinks there might be a simpler explanation. “Women, in general, have the ability to value people’s humanity at any age,” she tells me. “There isn’t really a point at which we render people useless because they get older. And we don’t necessarily dismiss them because they’re younger.”

Stylist Patricia Field agrees. “I never think about age. My whole life has been with younger people. I like being around them.” She first met her close friend Sandy Armeni in Greece ten years ago, when she was 65 and Sandy just 19. “I liked her energy from the beginning.” The two grew so close they eventually lived together, first for seven months in Pat’s apartment while Sandy looked for her own place, and then another five months in Sandy’s while Pat’s was being renovated. “We never fought,” Sandy says. “Not in her big house or at my tiny place. We spent a lot of time cooking at home, drinking, smoking cigarettes, and talking about life.”

My older friends are opinionated, smart, culturally-aware, and incredibly open-minded. They share what another friend Gina Pell would say is a “Perennial” mindset. Gina is the co-founder of The What and a successful entrepreneur several times over. We first met seven years ago, when I was 26 and she was 42. She was sharp and witty and she ordered white wine at lunch. She treated me like her professional equal, something that meant a lot to me at a time when I was a young person who had recently been given a lot of responsibility and was feeling decidedly in over my head. “Having friends of all ages helps me to integrate all the pieces of myself,” she says. “They help me remember who I was, who I am, and who I might someday become.”

Last fall, an essay she wrote on her frustration with generational segmentation went moderately viral after she coined the term and suggested grouping people by what they care about rather than their age — that there was a far more valuable cohort to be found in people “of all ages who … know what’s happening … stay current with technology, and have friends of all ages.” For Gina, cross-generational friendships are just a part of her life. “I’ve always had a wide range of friends and bonded with everyone, from 8 to 98. I think because of social media, we’re just seeing it more.”

But why now? Cross-generational relationships aren’t new. Go back a few generations and it wasn’t uncommon for people to live their entire lives in familial communities with lots of opportunity for intergenerational interaction. In many places, that’s still the case. But there’s a difference between proximity and choice. And that’s where the internet comes in.

If, for the last few decades, technology has been one of the markers we used to define generations — the personal computer and Facebook (millennials), smartphones (Generation Z), records and televisions (Baby Boomers), typewriters and cassette tapes (Generation X) — it’s also made connecting them even easier. We make friends out of common interests. And those interests have never been more communal.

According to Dr. Andrea Bonior, a licensed psychologist and adjunct professor at Georgetown University who’s literally written the book on friendship, we also make friends through repeated contact. “It breeds familiarity. And we tend to feel more positively about people after we are more familiar with them.” Technology both opens up that process (to friends we meet online, say) and enhances it. “Digital platforms allow us to follow up and build on something, so that you don’t have to start from scratch every time you see somebody. You can actually grow the conversation.”

And as much as we complain that digital connectivity has blurred the line between our work and personal lives right into oblivion, in many instances, it’s also encouraged us to consider our co-workers — our most common source of intergenerational exposure — our friends. “Twenty years ago, you might have had a senior colleague that you really liked, but the boundaries between work and home were stronger,” Dr. Bonior points out. “Now you’re working longer hours alongside them, and emailing or texting with them on weekends.” There’s that whole proximity thing again. Throw in the fact that office culture has grown significantly more casual, particularly in media and technology, and the intergenerational groundwork has been laid.

Culturally, we’re also doing things later — getting married, having children, going back to work, changing careers — if we’re doing them at all. And that variance means a lot more opportunity for intergenerational intermingling: A 48-year-old and a 30-year-old could meet picking up their toddlers from the same daycare. That life stages no longer align along generational divides has given us yet another opportunity to bond.

Kate Gardiner, 31, and Susan McPherson, 52, met through a women’s networking platform called The List (of which I am also a member.) “Susan was one of the first people to reach out and say “Hi, this is what I do with my life — what do you do with your life? How can I help you?” Kate tells me over the phone. The pair struck up a friendship through professional projects, but grew closer in their attempts to navigate the notoriously choppy waters of New York’s dating scene. “I’ve been single in New York for six years,” Kate says. “So when Susan was coming back on the market, she was like, how the fuck do I do this?”

“If I didn’t have Kate, I don’t know how I would keep current on all the dating stuff,” Susan laughs, before adding, a little more earnestly: “We all want to find the fountain of youth and there is something intoxicating about being around the energy that young people have. It’s a magical, magical feeling.”

Perhaps most importantly, there’s a desire — stoked by the giant orange-haired elephant in the room — to connect with other women not just regardless of age, but because of it. Adoara Udoji, a 52-year-old media executive, tells me she’s been inundated with conversations on the topic. “I’ve always had friends of different ages, but I’ve never had as many women reach out to me about their desire for intergenerational friendship as I have post-election. There was so much shock in terms of the demographics — both generationally and then the gap between white women and women of color. I know so many women who are deeply involved in politics who are like, ‘We don’t have any young women in our life. We need to know what they’re thinking.’”

So Adoara teamed up with a friend — a 25-year-old one — to do something. The pair are currently planning an all-ages brunch. “We’re going to sit women at tables with all different age groups. We’re going to get them talking to each other.”

My friends and I haven’t shared any life transitions. In fact, I’d go so far as to say we bonded in spite of them. I’m 33, in a committed relationship but unmarried. I own a dog but rent my apartment, and wake up hungover most Sundays. And as someone who is ambivalent at best about having children, I think a lot about how my life might change if I had them, or what my weekends will look like if I ever officially settle down. Like my sisters before me, I am taking my sweet time growing up. I like my life as it is now — I like who I am now — and part of what I fear about getting older is losing that clarity. But thanks to the friendship these women have given me, I feel like I’m getting a little peek at what my life could look like, especially in instances where the path I’m pondering (in my case, not having children) is a little less traveled.

When I see Brandon celebrate her 50th birthday with a surf trip to Rincon, I don’t just think: I want that. I think: I can have that. When I see the way Sarah Gray balances her success and ambition with her ability to just turn everything off and have fun, I think: I can do that, too. And when I see how Julianna takes the resources — time, energy, money — that often go towards raising children and instead dedicates them to her friends and family, I think about all the different ways women can be fulfilled and choose to fulfill others. And that it’s my choice to make.

When Your Best Friend Is Younger Than Your Daughter