Once Upon a Friendship

Rewriting the Stories of Life

"Life can only be understood backwards; but it must be lived forwards."
— Søren Kierkegaard

As we age, is it inevitable to feel the pull of nostalgia? As we approach milestone birthdays, a certain wistfulness settles in—the kind that makes you sift through old photos and wonder how the people you once shared life with are doing now.

As I edge closer to 50, I find myself in this headspace. It’s not that I’m yearning for the past—I’ve always prided myself on being forward-looking—but something about this phase of life urges me to take a longer, more thoughtful glance in the rearview mirror.

This nostalgia has a surprising twist: reconnecting with old friendships.

This is new to me. I never used to seek out people from my past; I’ve spent most of my life looking forward, often shedding relationships as I went.

In my youth, I romanticized friendships, believing that some bonds were like family—unshakable and permanent. But life, as it does, taught me otherwise. Over time, I became more practical and guarded about relationships. Yet here I am, reaching out, reminiscing, and rediscovering people who once played important roles in my story.

I’ve realized that nostalgia isn’t just about longing—it’s about honoring what brought us to where we are today. In the process, it can reshape how we think about relationships, our past selves, and the stories we continue to write.

The journey is heartwarming and bittersweet. But if there’s one thing I’ve discovered, reconnecting with the past isn’t about reliving it—it’s about finding the threads that still matter and weaving them into the present.

As a kid, I believed friendships were forever—etched in stone, like some cosmic decree. I imagined my closest friends and me growing old together, swapping stories of our shared adventures while sipping a drink on some porch decades later. To my younger self, friendships were my chosen family, my “team,” who always had my back, no matter what. But life, as it often does, had other plans.

Friendships, I learned, aren’t always the unshakable foundations we imagine them to be. They’re more like rivers—sometimes they flow together, sometimes apart, and sometimes dry up, leaving only the memory of their carved path. Back then, though, I couldn’t see that. I was too busy trying to hold on, convinced that losing a friendship meant failing.

I can still remember the first time I felt the sting of a friendship fading. It wasn’t dramatic—no fight, betrayal, or grand falling-out. We drifted, our once-parallel paths diverging without either of us realizing it. It felt like losing a part of myself, and I couldn’t help but wonder: wasn’t this supposed to last forever?

My younger self had a romanticized view of relationships. Friendships were like family heirlooms—meant to be cherished and preserved, no matter the cost. What I didn’t understand then is that the value of a relationship isn’t measured by its length. Some friendships are meant to last a lifetime; others, just a season. Both can leave an indelible mark.

Youthful idealism makes you believe in things that don’t always align with reality. I thought my “team” would stand by me forever, through every twist and turn. Instead, I learned that friendships, like everything else in life, require care, attention, and—perhaps most importantly—the ability to let go when the time comes.

Still, there’s something endearingly naive about how I saw friendships back then. I truly believed I could create this perfect circle of lifelong companions. It didn't happen. And yet, those friendships—however fleeting—helped shape the person I’ve become.

I’ve come to see friendships in youth as training wheels. They teach us how to connect, trust, and sometimes fall and pick ourselves back up again. Losing them isn’t a failure; it’s a rite of passage. It reminds us that relationships are living things, not fixed points in time. And as bittersweet as that realization can be, it’s also liberating—because it makes the friendships that endure all the more meaningful.

So, while my younger self may have believed in forever, my older self knows better. Friendships aren’t meant to be permanent—they’re meant to be authentic. And that is more than enough.

Why does midlife often pull us back to the friendships we once thought we’d outgrown? Is it the clock's ticking, a heightened awareness of our mortality? Or maybe it’s the desire to revisit the stories that shaped us, to reconnect with the people who knew us when we were still figuring out who we wanted to be.

Whatever the reason, I’ve been doing just that—reaching out, reminiscing, and rekindling old connections.

This wasn’t something I planned. I’d been content with my more practical, measured approach to relationships for years. Friendships were about the present—what we bring to each other now, not what we shared years ago. But as I was approaching 50, something shifted. I started wondering about some people I used to call friends. What became of them? Were they happy? Did they think about me, too?

There’s a vulnerability in reaching out after years of silence. The questions linger: What if they don’t respond? What if we’ve changed too much? What if the connection we once shared isn’t there anymore? And yet, there’s also something profoundly satisfying about rediscovering those ties, however tenuous they may be.

Midlife gives us a unique lens through which to view these old friendships. In our youth, we often focus on the intensity of the connection—how much time we spend together and how aligned our interests are. But now, I appreciate something else entirely: the shared history. Something is grounding about talking to someone who remembers the exact moments you do and can finish your sentences because they were there with you.

I’ve also shifted my expectations. Reconnecting isn’t about recreating the past; it’s about honoring it. I don’t expect these friendships to pick up where they left off or become my life's center again. Instead, I approach them with curiosity and gratitude—a chance to see how far we’ve both come and to celebrate the parts of our stories that overlap.

Of course, not every reconnection has been seamless. Some people have moved on completely, and that’s ok. Others have welcomed me back with open arms, and those moments feel like finding a piece of myself I didn’t realize I’d been missing.

One friend, in particular, reminded me of something I’d forgotten about myself. They laughed as we caught up and said, “You’ve always been like this—curious, reflective, a little stubborn.” It was a simple comment, but it brought back memories, reminding me of who I was before life layered on its complexities.

Reconnecting with the past isn’t just about nostalgia; it’s about understanding who we are now. The people who knew us then hold a mirror to our younger selves, helping us see how we’ve grown, where we’ve stayed the same, and what matters.

Nostalgia is a strange companion. It sneaks up on you when you least expect it—hearing a familiar song, catching a whiff of a scent that transports you back decades, or stumbling across an old photo that makes you pause and think, Was it that long ago? But here’s the thing: nostalgia isn’t about wanting to go back. It’s about cherishing the moments that brought us to where we are.

For a long time, I misunderstood nostalgia. I thought it was the enemy of progress, a distraction from the here and now. But I’ve come to see it differently. Nostalgia isn’t an anchor that drags us back—it’s a bridge that connects who we were to who we’ve become. It allows us to visit, reflect, and bring the best of the past forward with us.

Revisiting those memories offers warmth but also a sting. Nostalgia doesn’t just highlight what we’ve gained; it reminds us of what we’ve lost—friendships that faded, opportunities that slipped away, and versions of ourselves we’ve left behind. It’s a double-edged sword, offering comfort and clarity in equal measure.

For me, nostalgia often feels like flipping through an old yearbook. At first, there’s joy—remembering the good times, laughing at outdated hairstyles and inside jokes. But then, there’s the inevitable cringe, the sharp awareness of how much has changed. And yet, even those moments of discomfort are valuable. They remind us that growth isn’t always pretty but necessary.

What fascinates me most about nostalgia is how it evolves. In my twenties, it felt indulgent—a way to cling to the “good old days.” In my thirties, it felt impractical, like a distraction from the pressing demands of the present. But now, approaching fifty, nostalgia feels like a quiet teacher, nudging me to reflect on what truly matters.

Nostalgia is deeply personal. The same memory that fills me with warmth might mean nothing to someone else. It’s not the event itself that matters; it’s the story we attach to it. Nostalgia becomes a way of weaving together the moments that define us—a tapestry of triumphs, mistakes, lessons, and connections.

But it’s not all heavy reflection. Nostalgia has a playful side, too. Sometimes, it’s as simple as revisiting an old favorite movie or indulging in a food you haven’t tasted since childhood. These small acts of rediscovery remind us that joy isn’t always about creating something new—it can also be about appreciating what already exists.

In the end, nostalgia isn’t about living in the past; it’s about learning from it. It’s about recognizing the threads of our story, honoring them, and using them to weave the next chapter. Like an old song we haven’t heard in years, nostalgia strikes a familiar chord—and in doing so, it reminds us that while the melody may change, the music is always ours.

Friendships don’t have to follow the scripts we write for them. Before, I considered friendship an all-or-nothing proposition—best friends forever or nothing. Now, it's different. Friendships can ebb and flow, adapt and transform, and still hold immense value, even if they don’t look like I imagined.

Reconnecting with old friends has reinforced this lesson. One of the most unexpected gifts of these reconnections has been the ability to appreciate people as they are today, not as I remember them.

It’s no longer about picking up where we left off; it’s about meeting each other where we are. There’s something liberating about letting go of old expectations and simply enjoying the connection for what it is rather than what it could be or what it was.

I’ve also learned to approach these relationships with curiosity and gratitude. Curiosity allows me to see old friends through fresh eyes, discovering who they’ve become and how they’ve navigated their paths. Gratitude reminds me to cherish our shared history, even if our present lives look very different.

These experiences have reshaped my understanding of relationships. I no longer see them as a static bond but as a living, evolving connection. Some friendships endure because they adapt to the changes in our lives; others fade because they’ve fulfilled their purpose. Both are valid, and both leave an imprint.

If there’s one advice I’d offer about reconnecting, it’s this: start with openness. Don’t let fear of rejection or awkwardness hold you back. Reach out with no agenda other than to say, “I was thinking of you, and I’d love to catch up.” It’s a small gesture but can open doors to conversations you didn’t know you needed.

These experiences have shaped my perspective on friendship and life. Approaching 50 feels like standing at a crossroads, where the road ahead is as important as the one behind.

But perhaps the most important lesson is this: friendships don’t have to last long to be meaningful, and they don’t have to look a certain way to matter. Whether they endure for decades or just a fleeting season, they shape us in ways we often don’t realize until much later.

I’ve embraced the idea that reconnections aren’t about recreating the past but deepening the present. Nostalgia has shown me that our stories are never finished, and the people we’ve loved—no matter how briefly—are part of the fabric that makes us who we are.

Here’s to the friendships we’ve kept, those we’ve let go of, the ones we’re rediscovering, and the new ones we’re making. If you fall into any of these categories, thank you! I’m so happy we’ve shared part of the journey.

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Book Recommendation: The Road to Character by David Brooks

Before we wrap up, I recommend David's book The Road to Character. It’s a powerful exploration of what matters in life—our relationships, struggles, and growth. He contrasts “résumé virtues” (what we achieve) with “eulogy virtues” (who we are), reminding us that our character is shaped not by perfection but by how we navigate life’s complexities. It’s a book that doesn’t give you answers but invites deep reflection—the kind of reflection nostalgia often stirs. I hope it resonates with you as much as it did with me. Let me know if it does.