My nerves buzzed as I waited for my 23-year-old friend I’d never met in person to join me for dinner. Standing in line at a trendy Italian restaurant in New York City’s Greenwich Village, I caught a glimpse of my 45-year-old self in a store window. I shifted my dress and attempted to muffle my Chicago accent even as I mouthed nervously to myself, what if we have nothing to talk about?
I relaxed the moment I saw her. Jacqueline warmed the room with the same smile I’d seen on my laptop screen for over a year, and we had one of those magical nights that would be hard to replicate. Throughout dinner both the prosecco and conversation sparkled as we elaborated on the essential edges of life that new friends need to become privy. Everything was in sync. Much like our friendship.
Jacqueline and I are two sides of a triangle, completed by our friend Helene, who missed our dinner while out of the country during my visit. The three of us affectionately call ourselves “20-40-60,” an homage to our respective ages — 23, 45 and 60.
I met them both last year after I set aside decades of corporate success to follow my passion by taking an online writing class. We shared our drafts in coordinated folders and dialed in through video conference every single week. The highly personal business of writing proved a vulnerable launchpad through which to bond.
I wasn’t looking for new friends. In fact, I have a robust social life including seven lifelong friends whose stories are intrinsically intertwined with mine. We’ve seen each through every wedding, maternity ward, a handful of divorces, parenting struggles, our own parents dying. There’s endless comfort, yet zero surprises.
With Helene and Jacqueline, we became acquainted through essays — the one I wrote about playing poker to get closer to my dad, the story of how I became friends with my ex-husband’s ex-wife, and countless drafts in between. We pasted our work in shared documents, ready to line-edit, debate, brainstorm and discuss. Even the shameful bits I didn’t want the world to know, I shared with them.
Intergenerational friendships may seem rare, but according to an AARP study, 37% of adults have a close friend who is at least 15 years older or younger than them. Many meet through work, or like us, in a class.
We know a great deal about each other through our writing. Helene and Jacqueline could tell you every beat in my head as I calculated the risk in dating my now boyfriend after two divorces. They know about my dad, the elusive competitor I’m always trying to impress. I feel keenly aware of Jacqueline’s loving yet complicated relationship with her parents, and Helene’s turmoil as a Jewish mother over the terror attack on Israel on Oct. 7, 2023. I’ve even spoken to Helene’s husband on the phone and I know each ingredient in her famous banana cake recipe.
“Wait, what’s an example of a Gen Z pickup line?” We giggled one night on our weekly Zoom, realizing some things don’t change with age. We give perspective on things otherwise invisible. We are the friends who know each other well enough, but without the baggage of a history of life lived next to one another.
We give perspective on things otherwise invisible. We are the friends who know each other well enough, but without the baggage of a history of life lived next to one another.
“Oh, Andrea, I know what you should write about!” Helene exclaimed, along with a thoughtful explanation that makes me think this woman, who I still haven’t met in person, may just be opening an otherwise inaccessible window to self-discovery.
Eventually our weekly hourlong meetings whizzed by too quickly to satisfy our needs, so we emailed and texted between Monday nights. I saw this and thought of you. Why don’t you use this for your grad school application? Have you ever thought about …
I’m amazed that typically the answer for me is, no I actually haven’t thought about that yet. How is it that they know me better than my lifelong friends?
I was raised in a highly competitive household and carried a misguided, if generic, view that success meant reaching certain milestones — buy a condo by 25, marry by 30, have kids quickly, retire at 60. These pressures created an artificial sense of urgency and anything that blew me off course — including losing my job, two divorces, and not having children — left me feeling like a mangled wreck in the ditch below the pre-paved path.
I spent 20 years building my identity based on my corporate achievements. When I joined the writing group, it felt like I had stripped myself bare to a likeness that I wasn’t sure the world would appreciate or even accept. None of my lifelong friends understood why I’d give up the comforts of steady employment.
I’ve had spells of doubt within almost every aspect of my writing. Am I framing this up the right way? Am I smart enough? Am I good enough? Through each impasse in my psyche, these two friends helped clarify what was possible — an image otherwise out of focus.
Helene, with her decades of lived experience, helped me reframe a career crisis as an opening for reinvention — a chance to shed old identities for new possibilities. From a similar corporate background, she shared her own stories of the balance between motherhood and the boardroom, when she had to reinvent herself not once, but multiple times.
Jacqueline’s youthful energy reminded me of the excitement of starting fresh, of approaching the unknown with a willingness to experiment. She had yet to become jaded by the pressures of adulthood, and her optimism helped me reconnect with my own sense of possibility. Through her, I was reminded of the value of new perspectives, along with this phenomenal gift Gen Z can bring to all generations — self-possession. She represents the open-hearted future society needs.
I logged into the writing group last week; it’s my safe emotional space. We ended up talking long past our planned hour. I logged off with pages of notes on topics that may be relevant for me to explore. Jacqueline walked away with a dating prospect in Helene’s friend’s son — a sweet and single musician. Helene, who’s been happily married for 35 years, got a crash course in Tinder jargon.