In midlife, a shared history may not only help establish friendship—it may be necessary.
What now?” Tom asked me after I broke the news. I think I knew pretty quickly after our first date that we weren’t destined for romance, but I really liked him, so we kept seeing each other for a few months. Finally, reality had set in.
„Can we still be friends?” I asked him.
„Let me think about it,” he responded, sounding disappointed. „Maybe someday.”
My heart sank a little. I didn’t want him to be my boyfriend, but I didn’t want to say goodbye either. I remembered how his wry take on subway riders had made me chortle —how the article about fascism had sent me down an internet rabbit hole—how we jousted playfully about politics.
„I’ll miss you,” I said, and meant it.
The end of a romance, even a brief one, is always a little sour. You’ve opened yourself up and scrolled through your stories until you’ve arrived at an attractive version of yourself. You’ve weathered the awkwardness of a first kiss, thrilled to the first flurry of texts and emails, opened yourself to the possibility of connection and then, all too often, that bright promise curdles into a familiar feeling of disappointment.
But what I have found is that what initially attracted you to a person need not be wasted. Like scraps from a lumber yard, it can be salvaged and used to build something new.
I’d been on plenty of first dates with people I never wanted to see again: the disrespectful jerks, the oblivious nerds, the self-absorbed bros. But then there were those I kept seeing because I genuinely enjoyed their company. Though the attraction may have waned, the shared interests, outlooks and senses of humor remained. I respected them. Why, I have often wondered, should the end of romance mean the end of everything?
I believe in friendship and chosen family. I’ve written about my relationship with my two best friends from high school, which has defined and enriched my life for almost four decades. I’ve nurtured close friendships from summer camp and college for decades, too. But since most of them live far away, I’ve had to find new friends I can see more regularly. It’s proven difficult.
At 53, a psychologist with a solo practice, I no longer have school or workplace to encourage contact. A promising prospect in my yoga class fizzled out after one coffee date; a Hebrew school parent fell away after a faltering text exchange. I’ve never been one to join clubs, and my volunteer gigs and religious community, though rich in lots of ways, have proven fruitless in the friendship department. In fact, apart from my single mom friend group where we share the built-in intimacies of child rearing, the only durable friendships I’ve made in the last decade have been with men I once dated.
A 2020 American Journal of Psychiatry study found that people who enjoy close friendships are not only more satisfied with their lives but less likely to suffer from depression. But research also shows that middle age can be a hard time to find new friends.
According to a global study undertaken in 2019 by the popular app Snapchat, „The Friendship Report,” the average age at which we meet our best friends is 21. Remote work has made the pursuit of new friends even more complicated. Last year, the U.S. surgeon general released an advisory underscoring the seriousness of loneliness and isolation.
Without the scaffolding of formal communities, it can be hard to find meaningful connections in midlife. Young adulthood is a time when we not only have many social contexts, but plenty of time in which to explore them.
We tend to become much more inflexible and pickier as older adults, so the pool of possible friends shrinks, as does the time necessary to connect with them. A 2018 report found that „it takes roughly 50 hours together to move from mere acquaintance to casual friend, 90 hours to go from that stage to simple friend’ status, and more than 200 hours before you can consider someone your close friend.”
Even if you’ve only dated for a few weeks, you’ve probably learned more about your erstwhile romantic partner than most new friends can learn in a year. It’s perfectly normal to bore in on a date with a barrage of questions—but a new friend you’ve met in yoga class? That kind of intensity would be grounds for a permanent ban. Even though romance wasn’t in the cards for Tom and me, for example, I learned a great deal about his loves and losses— deep stuff indeed. While the gap between dating and friendship may feel vast in your 20s, it narrows greatly in middle age.
A few weeks after our parting, I contacted Tom one more time. To my delight, he wrote back.
„Let’s hang out,” he texted. „I thought about what you said. Let’s give it a try.”
It wasn’t a seamless transition from dating to friendship. Brutal honesty and firm boundaries were required. Before we could get past the jagged
edges of failed romance, we had to create a shared narrative about what went wrong.
„What happened?” Tom asked at our first post-breakup meet-up.
I swallowed hard and chose my words carefully.
„I couldn’t see a romantic future for us,” I told him. „It just wasn’t there. But that doesn’t mean I don’t care deeply for you. Can we reframe this? Is that possible?”
After the initial anger and subsequent awkwardness subsided, we did indeed become close friends. More than that, we felt like we’d been through something together. A shared history, even if disappointing, is fertile ground for intimacy and is especially hard to create in middle age.
Your dating life may feel like a series of disappointing encounters, but only if you measure success by enduring romantic relationships. My dating days are long over—I’ve been happily committed to my current partner for four years, and I’ve reveled in my friendship with Tom as well as a handful of other exes.
Tom’s wry observations still make me laugh, his insight into my teenage daughter has helped me cope, and his political takes have enlarged my world. Sometimes I wonder if it would have been possible to
forge such a close friendship without our failed romance as a catalyst. In fact, in midlife, without a common uniting context like school or work, a shared history like the one I created with Tom may not only be a good ingredient to establish friendship—it may even be necessary.
Sarah Gundle, Psy.D is a psychologist in private practice and an Assistant Clinical Professor at the Icahn School of Medicine, Mount Sinai Medical Center. She’s written for the NY Times, WA Post, Newsweek, Huff Post, Salon, NBC, CNN, Bloomberg and Wired. All views expressed are the author’s own.
TASK 3
Task description: Students will participate in a discussion about friendship, romantic relationships, and connections in midlife.
Task elements:
1. Summarize in a few sentences how Sarah and Tom changed their relationship.
2. Explain why the author believes a failed romance can lead to strong friendship.
3. Compare and contrast friendship in youth (school, university) vs. midlife. Create a mini-chart.
4. Debate: Is friendship with an ex a good idea? Vote and defend your position with reasons.
5. Design a 6-step guide for how to stay friends after a breakup. Present it like „expert tips.”
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