I Joined the Mile High Club with My Boss
- By: Amanda Coscarelli
This story has been submitted by a LOOP reader…
It started as a work trip and ended somewhere between reckless, intoxicating, and impossible to undo.
I wish I could say it was completely unexpected—that it blindsided me somewhere over the Midwest, that I had no idea how quickly things could spiral when you mix ambition, proximity, and two glasses of airplane wine. But that wouldn’t be entirely true. I knew there was something there before we ever boarded the flight.
He was my boss, technically. Not in a vague, corporate-hierarchy way, but directly—my editor, my gatekeeper, the person who approved my pitches and rewrote my headlines at midnight. He was sharp, impatient, and annoyingly perceptive. He was the kind of person who could dismantle your work in three sentences but also make you feel like you were the only one worth investing in.
We worked late a lot. That’s how it started. Lingering conversations after deadlines. Slack messages that drifted from strictly professional to “Did you see that place downtown?” Then drinks “to celebrate a good week,” which turned into drinks because it was Thursday, then drinks because neither of us had anything better to do. Nothing explicitly crossed a line—at least not in a way you could point to. But the tension was there, humming just beneath everything.
The work trip was supposed to be straightforward. A quick flight, one night in a hotel, meetings the next morning. We even joked about how uneventful it would be.
“You and me, stuck on a plane for three hours,” he said at the gate. “What could possibly go wrong?”
I laughed it off, but something about the way he said it lingered.
We were seated next to each other—of course we were. Economy, middle and aisle, knees brushing every time one of us shifted. It felt ridiculous how aware I was of him. The way his arm rested too close to mine. The casual way he leaned in when he talked, like the rest of the plane didn’t exist.
Nothing explicitly crossed a line—at least not in a way you could point to. But the tension was there, humming just beneath everything.
The first drink came quickly. Then another. At some point, the conversation shifted. It wasn’t about work anymore. It wasn’t even about anything important. Just stories, confessions, the kind of easy honesty that only happens when you’re suspended somewhere between cities, between responsibilities, between versions of yourself.
“You’re different up here,” he said quietly, glancing at me.
“Different how?”
“Less… careful.”
I should have laughed it off. Changed the subject. Done something smart, something responsible. Instead, I said, “Maybe I just don’t feel like being careful right now.”
That was the moment. The pivot point.
Everything after that felt like a series of small, irreversible decisions. His hand brushing mine and not moving away. The silence that stretched just a second too long. The look that said, Are we really doing this?
When he stood up and nodded toward the back of the plane, it didn’t feel like a question. I followed him.
The airplane bathroom is exactly as unromantic as you’d expect—cramped, loud, barely enough room to turn around. And yet, somehow, it felt surreal, like we’d stepped into a completely separate reality, one where consequences didn’t quite apply. There was no grand declaration, no dramatic buildup. Just a split-second hesitation, and then the kind of impulsive decision you can’t take back. It was quick. Clumsy. A little ridiculous, honestly. We both laughed at one point, trying to keep quiet, the absurdity of it hitting us all at once. But it was also electric. Not because of what we were doing, exactly—but because of who we were doing it with, and how undeniably wrong it was.
When we slipped back to our seats, nothing looked different. The same passengers, the same hum of the engines, the same half-empty cups on our tray tables. But everything had changed.
We didn’t talk about it right away. Just sat there, facing forward, like we were both trying to process what had just happened.
Finally, he said, “That probably shouldn’t have happened.”
“No,” I said. “Probably not.”
A pause.
“Do you regret it?”
I looked out the window, at nothing but clouds and fading light.
“I don’t know yet.”
It felt surreal, like we’d stepped into a completely separate reality, one where consequences didn’t quite apply.
That was the truth then. It’s still the truth now, if I’m being honest. Because here’s the thing no one tells you about crossing a line like that—it’s not just about the moment. It’s about everything that comes after.
The next day, we went to our meetings like nothing had happened. We were professional. Polished. Completely in sync, like always. But there was an undercurrent now. Something unspoken but impossible to ignore. Every glance lasted a little too long. Every casual interaction carried weight. And suddenly, everything felt complicated.
Back at the office, it didn’t disappear. If anything, it intensified. Because now we had to navigate this strange, invisible line between what we were supposed to be and what we’d already become. We never talked about it in a serious way. No rules, no agreements. Just an understanding that it existed—and that it couldn’t, or shouldn’t, happen again.
But tension like that doesn’t just fade. It lingers. It reshapes things. It makes you question every decision, every ambition, every late-night message that pops up on your phone.
People love the idea of the Mile High Club. It sounds glamorous, rebellious, cinematic. But the reality? It’s messy. It follows you back down to earth.
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