WHEN YOU'RE LOVING
19. The One That Got Away
"What we call the beginning is often the end. And to make an end is to make a beginning. The end is where we start from." —T.S. Eliot
Dear Kids,
Twice now I've told you that circumstance and timing are the one variable no framework can solve. This last letter on love is what that sentence actually feels like from the inside.
Sometimes, when I look back, there are people I've encountered who leave me pondering, asking the quiet yet powerful question: what if? What if I had spent more time with this person? What if we'd met earlier, before life set us firmly on our separate paths, and built a future together? These moments linger, quietly haunting, quietly beautiful.
Sometimes it just hits you on a random Tuesday afternoon, completely unexpected. Life has shifted subtly, silently, yet profoundly. Suddenly, news of an engagement floods your timeline, instantly transporting you back to late-night talks until 4 a.m., to shared laughter over inside jokes that felt like treasures only the two of you held. You realize, with bittersweet clarity, that perhaps those clichéd, drunken love songs belted out on the radio weren't so far off the mark after all.
Perhaps it's the mystique of who she was, or the tantalizing possibility of who she might have become. Maybe it's merely the enchantment of an unknown future, the human tendency to romanticize roads not taken. Or maybe, just maybe, it's simply that evergreen phenomenon — the grass appearing greener on the other side. Still, despite knowing this, I find myself pausing, wondering, dreaming about how life could have unfolded differently.
Sometimes you meet someone and you instantly recognize that if circumstances had aligned differently — if only you'd met sooner, if your paths had crossed at a different juncture — you could have built something extraordinary together. This person complements your very essence, perfectly balancing who you are. Simon Sinek describes three crucial criteria in relationships: physical attractiveness, intellectual assimilation, and emotional compatibility. Yet, there's a fourth, elusive factor — timing. Timing is that sticky, relentless thorn that pricks us painfully, reminding us that some things lie beyond our control. I wrote you, in the last two letters, that circumstance was the one variable no framework could solve. This is what I meant. It's the stubborn, persistent ache of knowing that if this person had arrived earlier, or if I had been older, the path ahead could have been breathtakingly beautiful.
I'll tell you the version that lives in my head, without telling you who she is — because that would be a betrayal of both of us, and because the specifics don't really matter for what I'm trying to say. There was a person who walked into my life at almost exactly the wrong moment. Wrong city, wrong year, wrong version of me. Everything that should have aligned didn't — not because either of us did anything wrong, but because the calendar refused to cooperate. We stayed friends. We pretended we were fine with it. Sometimes we even were. But there is a small ache, still, that I haven't been able to file away under any neat category. It just sits there, occasionally, when a certain song plays.
As I grow older, I realize it's rare — extraordinarily rare — to feel this deep resonance with someone. Youth comes cloaked in potential and innocent optimism, allowing us to embrace people without the rigid criteria we develop over the years. Our younger selves welcome uncertainty, our hearts open, unguarded. Naivety shields us from cynicism and guards our spirits against becoming overly cautious.
But age sharpens our discernment, perhaps too sharply. We begin noticing patterns, pathways, and become selective — sometimes excessively so. Relationships transform from explorations into assessments. People become set in their ways, their identities largely fixed. Unlike the fluidity of youth, adulthood confronts us with a choice: embrace this person as they are, or move on.
I wonder if, years from now, I'll look back on this very reflection and find it naive as well. Perhaps. But there's an undeniable truth in acknowledging the fleeting nature of connection. When younger, I undervalued relationships, believing I had all the time in the world. But time, relentless and unyielding, moves swiftly forward, transforming intimates into strangers.
Every so often, a pang of regret surfaces. It's subtle yet piercing, gently forcing the question again: was she the one that got away? The "what ifs" echo softly but persistently, reshaping the world in my imagination, and with it, the life I might have led.
I also want to be honest about the other side of this. The grass-is-greener voice in your head is, often, lying to you. Memory is a generous editor — it crops out the part where the timing was wrong for real reasons, where you weren't yet who you needed to be, where the version of you that loved them couldn't have built anything lasting with the version of them you actually had. The "one that got away" sometimes got away because they were supposed to. Not every door that closes was a door you should have walked through. That's the counterargument I have to keep making to myself, and I'm not always sure I'm right.
Kalanithi comes back into the picture here, too. The part of When Breath Becomes Air that stayed with me on a long flight back from Cambridge wasn't the part about dying. It was the part about choosing. He could have been three different versions of himself — the literary scholar, the doctor, the husband — and he writes, near the end, with the calm of someone running out of time, about how the paths he didn't take were never really lost; they were the cost of the path he took. You don't get all the lives. You get this one. The "what if" is real, but it isn't a referendum on your worth — it's the price of admission for actually having lived a particular life rather than vaguely hovering above a menu of possible ones. Reading him made me less melodramatic about the people I didn't get to keep. The road not taken isn't a tragedy you suffered; it's the shape of the road you're actually on.
Ultimately, perhaps the beauty — and pain — lies precisely in this ambiguity. The unanswered questions, the quiet moments of reflection, and the infinite possibilities we never fully realize. These musings are not merely nostalgic indulgences; they are reminders of our humanity, of chances taken and missed, and of love's delicate, fleeting grace.
And so, kids, my advice for you is to savor those moments of spark and connection, especially when you're young, when life holds so much potential for you — and so do other people. Embrace the thrill of possibility, the excitement of building something unknown and beautiful together. When you find someone who genuinely stirs your soul, don't let them go lightly. Tell them. Sit through the awkwardness of saying it out loud. The version of you that didn't say anything will quietly outlast the version of you that did, and not in the way you want.
May you live a life filled with fewer regrets and richer connections.
May you never look back and think of someone as "the one that got away."
And if you do, may you be kind enough to yourself to remember that the timing, sometimes, is just the timing. It isn't a referendum on your worth, or theirs.
Love,
Dad.