I still remember the flicker of neon outside the rooftop bar, the way the music gently thumped under our feet, and how for a moment I almost walked over. You looked over, I saw the hint of a smile—or maybe I imagined it—but something held me back. And now whenever I see a pair of people laughing under city lights I wonder: what if I had just walked those few extra steps?
It was a Friday, the kind of night when New York feels infinite. I’d come out with friends to celebrate finishing a big project, sun setting early, the skyline glittering, windows alive with stories. We ended up at this rooftop bar, full of energy and strangers and possibility. You were alone, leaning on the railing, a drink in hand, looking out at the city like you were hiding something. The sky was turning violet, clouds edged pink.
You looked comfortable, confident even, with a vintage bomber jacket and a laugh that caught beams of light. I caught the tail end of you telling someone about your old band—yeah I overheard—so I knew you had stories. My friends were off somewhere else, talking about the next bar, and there I was, between staying put and striking up a conversation. That’s when the miss happened.
I had this little voice in my ear: walk over. But I also had that voice that said: don’t interrupt. You looked like you belonged there, like you were at ease alone. And honestly I had just spent all week thinking about other people’s expectations. So I stayed back and stared instead.
For ten minutes I asked myself: “Do I go? Or do I not?” I almost whispered your name (which I didn’t know), almost started a “Hey, mind if I join you?” But I didn’t. My friend waved me over to another group. I hesitated, looked at you again, and then turned away. That was it—the missed chance.
Later, back on the subway heading home, I played the scene in my head. I pictured you at the bar, looking at the skyline, looking at me maybe. I imagined walking up, making an awkward joke about how high up we were, how small the cars looked, how big the stars seemed. Maybe you would have laughed. Maybe we would have ended up exchanging numbers, hopping to another spot, laughing in a cab ride home. But none of that happened.
Now when I think of “missed connection,” I don’t think of Craigslist ads titled “You were the girl on the third floor elevator wearing green” or “Guy in the blue beanie—where did you go?” I think of that moment when adrenaline and fear and expectation collide and you walk away. And you carry that until you wonder what you missed.
Why do we do that? Why do we step back, convinced someone else has it all together while secretly we’re certain we don’t? Maybe it’s the fear of being the first one to call it out. Maybe it’s the fear of messing up. Or maybe that silence between us felt safer than a conversation. If I said something, it could change everything. If I said nothing, I maintain this weird ideal of who you were in that moment.
In the days that followed, my mind kept orbiting that night. I kept replaying what you looked like under the amber lights, the way you tilted your head, how the skyline framed your silhouette. The memory softened into a half-fantasy. I couldn’t even recall precisely the color of your eyes. I just remembered the warmth. And the wouldn’t-we-have could-we-have.
It wasn’t just about you. It was about me. I realized I’d spent years watching from a distance—friends, relationships, opportunities. I was waiting for some perfect alignment when I could leap forward with zero risk. But life isn’t riskless. The rooftop was high and the night was young and yet I played it safe.
Then I asked myself: what does it take to say “hello”? Why do we assign so much weight to one sentence, one walk across a floor? It’s because we know the stakes feel high: this could be the moment you tell your future grandkids how you met. But we also know there is a cost: we could make it weird. So we default to nothing. And nothing becomes a regret.
I’m writing this because maybe you’re out there. Maybe you were watching the skyline and thinking nothing special. Maybe you went home, I don’t know. But if you show up in my memory again, I’d like to say this: “Hey. I saw you. You looked like you had stories. And I wish I’d asked just one.” And maybe you’d say: “Me too.” Or maybe you’d say: “Thanks. But I needed the silence.” And that would still be something.
The thing is, life keeps moving. The skyline changes, the friends keep dragging me to new bars, new rooftops, new chances. And I’m trying to learn something from that night. I’m trying to shift from watching the world to joining it. The next time I see someone standing alone just leaning into the view, I want to take the steps. I want to risk a fleeting awkwardness for a moment of connection. Because the ‘almost’ is starting to feel heavier than the mistake would have been.
You might not remember the jacket or the bar or me. You might remember exactly none of it. But I’ll carry it. And maybe that’s okay. Maybe that’s the point: some connections never happen, but they still teach us something. They teach us that we are alive and we are waiting—and that waiting sometimes turns into longing.
So here’s to missed chances. Here’s to rooftop bars and skyline silences. Here’s to the person who might’ve been the one if I’d said hello. And here’s to the one I hope I’ll say hello to next time. Because next time I’ll walk over. I’ll say something. Maybe I’ll mess it up. Maybe you’ll be surprised. But at least I’ll walk over. At least I’ll keep the chance from slipping away.
