After weeks of ricocheting between meetings, dinners, and subway rides in New York, I found myself with a rare, unclaimed Saturday in Miami. I pointed my car toward the newly opened Miami World Center and wandered into a wine bar called Sixty Vines.

I took a seat alone at the counter and ordered, perhaps a little too confidently for 3pm, a four-wine tasting flight and a three-meat charcuterie board. Borderline aggressive for one, perhaps, but I was midway through the latest Hunger Games on my Kindle, and it felt like the perfect afternoon for a miniature feast: small luxuries on the plate, dystopian drama on the page. A guilty pleasure for both mind and body.

An hour and a half later, the server approached with my check, and a question. “This may be a little strange,” she began carefully, “but… can I ask you something personal?” 

I nodded.

“Are you single?”

I said yes, bracing for where this might go.

“I couldn’t help but notice you,” she said. “There was something about the way you were just sitting by yourself, reading. You looked completely at peace. It was… kind of inspiring.”

We traded short stories across the narrow space of the bar and my now-empty glasses. Both of us had recently emerged from long-term relationships. The only other time I’d been to Sixty Vines was with my ex, during the week it first opened.

Our exchange was brief, but it felt as if we’d tugged at the same loose thread in the fabric of our lives – heartbreak, loss, and the quiet insistence to keep moving anyway. And in those few minutes, we had moved each other. She had seen my solitude and named it as something whole. I had reminded her it was not only possible, but enough.

I am no stranger to doing things alone. As a teenager, I once went to see a Harry Potter movie at the cinema by myself, simply because all my friends had already gone. In college, my first trip was a solo one to Madrid – back when smartphones didn’t exist and a dog-eared Lonely Planet guidebook was the closest thing to GPS.

This year, as I’ve had to rediscover what it means to be single, my solo experiences have multiplied – not just in frequency, but in meaning. Maybe it’s all been one long act of quiet rebellion. Or maybe it’s simply the slow, deliberate work of gathering back the parts of myself that were diluted, or quietly set aside, over five years of partnership.

A sampling from this year alone: the Chargers playoff game in Houston, tailgating and all. A lone drive to Breckenridge to meet a group of strangers on the slopes, even though my last attempt at snowboarding was a decade ago. The musical moments have been just as varied: an open jam in the basement of a pizza shop in Bushwick; a weekday Beyoncé concert, regrettable only for an unexpected New York spring storm. Each of these encounters has been a quiet reminder that sometimes, you don’t need a reason, a plan, or company.

Sometimes, you can just go. 

Sometimes, you can just do things.

I have treasured every one of these experiences, though the glances from those around me are hard to miss. Never sharp with judgment, but softened by a quiet confusion; an unspoken question hanging in the air. And yet, I’ve never once wished to share these moments. They were special precisely because I had them to myself.

On my most recent solo adventure, I booked a 48-hour trip to Puerto Rico, just three days in advance, to see Bad Bunny perform at his historic residency on home soil. The show is called No Me Quiero Ir de Aquí, which translates to I don’t want to leave here. After years of global stardom, it was Bad Bunny's homecoming – an ode to place, memory, and the roots that shaped him. In interviews about his latest album, Debí Tirar Más Fotos, he speaks about wanting to capture the feeling of coming home: musically, emotionally, spiritually.

As I stood among thousands of fans on an island I had never been to before, I felt the strange ache of being somewhere new while someone else returned to where it all began. I couldn’t help but think of Singapore – my own home, thousands of miles away – about to turn 60 and still less than twice my age. And me, still learning what it means to be both from somewhere and apart from it. Still figuring out how to build a life by myself, in a direction most people back where I’m from would never think to look. One that doesn’t wait for permission, or follow a path already drawn.

Eventually, I settled into my seat and let the music carry me. The concert, and San Juan itself, was every bit as magical as I’d imagined. My spot was between two couples, each sharing the moment in their own way. In both pairs, though, the men wore the unmistakable expression of someone reluctantly in attendance. While their partners stood singing every lyric, they slouched in their seats, occasionally scrolling through their phones or clapping a half-beat off.

It was a gentle and quietly amusing reminder that joy itself is a luxury: best when unfiltered, untempered, and entirely on your own terms.

Navigating singlehood after years of forgetting what it meant has been its own journey: liberating in ways I never expected, and yet, at times, unfamiliar. I’ve said yes to things simply because I wanted to. I’ve enforced boundaries that are mine and mine alone. I’ve learned the quiet pleasure of moving through the world on my own timeline, in my own orbit.

And still, deep down, I think a future would be nice to share with someone. Not just the big milestones, but the quiet, unremarkable parts. Things I once shared with someone every day – grocery runs and morning coffees, quiet glances across a crowded room that said, let’s go. The kind of unspoken rhythm that only time creates. I think about what it would mean to have a witness to the everyday, someone who sees the version of me that doesn’t need to perform. A partner in the long game. A co-architect of a life built brick by brick.

But the idea of commitment now feels heavier than it once did. Not because I fear love, but because I’ve only just begun to understand who I am without it. I worry about what I might lose in the process: the freedom I’ve fought to reclaim, the quiet satisfaction of choosing for myself. The spontaneity that sometimes looks a little reckless but feels like mine. I wonder if intimacy always comes with a cost: if to be loved, you must first be softened, then shaped. If saying yes to someone else means slowly forgetting how to say yes to yourself.

I don’t yet know how commitment makes room for that kind of wildness. I don’t know how love exists without the pressure to shrink.

I think back to that encounter with the server often. Something about my being alone must have given off a kind of energy… if not one of confidence, then at least of comfort. But while I’ve learned how to look comfortable, I’m still learning how to feel it fully.

And maybe that’s the art of being alone: not just knowing who you are without someone else, but holding on to the parts of yourself no one else gets to take.

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