THE BLOG
12/07/2015 04:16 pm ET Updated Dec 06, 2016

The Mile High Club

I once went to second base with a stranger on a plane. He was my seatmate on the red-eye from Los Angeles to New York. We never spoke or exchanged names. We never even said hello.

I'd spent the afternoon in LA at the Independent Film Awards with a man who'd been nominated. After a few weeks of casually seeing one another, I was already feeling like he was too old for me. Through a wacky series of mishaps that rivaled any comedy motion picture nominated that afternoon, I learned he was even older than he'd said... by a decade. I'd ended things later that night during a tense conversation on the way to the airport. After a long day of parties and social engagements, I was tired and in a strange mood.

I was already sound asleep on the plane by the time my anonymous seatmate boarded (a privilege of my frequent flier status). By the time I woke up again, meal service was over and the cabin lights dimmed for the duration of the flight, meaning I never really got a good look at him. But a few furtive glances led me to believe he was my type.

It started innocently enough. We were both using the armrest between us, and our hands accidentally touched. But instead of immediately readjusting to avoid contact - as per unwritten airplane protocol - we left them there, tentatively.

A few minutes passed. Neither of us moved. Somehow sitting there in the dark, saying nothing, with our hands touching felt intimate, as if it were the most natural thing in the world.

My mind was racing. I wondered if his was too. Were we flirting? Or had I (just) seen one too many Hollywood movies? It had been at least a half-hour and neither of us had moved our hands. It seemed as if we were trying to keep them together by that point - almost awkwardly so. Maybe it was just an overzealous case of Armrest Domination Escalation and we were in a standoff.

I'm so shy my wingman needs a wingman. I literally have no moves. But something about the day's events had coalesced into temporary insanity (I'm guessing) on my end, and I found myself unable to shake the thought: I wonder what would happen if I just leaned over and kissed this guy?

And the same way you can be standing at the edge of the high dive one second thinking to yourself, "Man, that's pretty high," and the next thing you know, you're jumping without really realizing you jumped... I leaned over and kissed him.

The thing about the red-eye is that eventually it lands. And when it does, harsh lighting and bad breath abruptly replace darkness and intrigue, and then you find yourself starring into the eyes of the man you've been canoodling the past two hours, and he appears to be 12.

Concerned, I jokingly asked what fraternity he was in. When he responded with actual Greek letters, thoughts of jail danced across my mind. My romantic comedy had taken a turn. Sensing my mounting alarm, he assured me he was 21(oh, so much better... thank you), and that today was in fact his birthday. He'd just graduated from UCLA (again, thanks), was moving to New York (via our flight), and would like to see me again. I'm sure for my brains and wit, and not because I was easy.

I explained that I was, I suppose ironically, on my way home from breaking up with someone who had been too old for me, and I didn't think throwing myself into another age-inappropriate relationship a mere nine hours later was prudent. He asked if he could at least know my name. I told him it was probably better he didn't, gave him my goody bag from the awards show as a consolation prize/birthday present and deplaned.

I wonder if he ever tells the story of "once, on a plane, this random lady who was really old leaned over out of nowhere and started kissing me, and then gave me an awesome swag bag," to his friends?

Another time I sat next to a woman on a flight from New York to Oslo. I didn't try to make out with her. In fact, neither of us said a word the entire flight. Not even after we landed and were taxiing to the gate. It was only after our plane had stopped, and we were gathering our bags while waiting to deplane that we began chatting. After only about two minutes, we decided we liked each other well enough to exchange contact information. We have stayed in touch ever since.

She lives in Norway. When she visited New York with her husband and son for a few days we made a point of all having dinner together. We wined and dined for hours, enjoying each other's company and a seven- or eight-course chef's tasting meal someplace fancy. It was like we'd known each other forever, from a two-minute exchange about how long it takes people to get off an airplane.

Airplanes are microcosms of society. Little metal tubes full of strangers, forced to sit together in close quarters for hours upon hours eating, drinking, working, relaxing, sleeping, grooming - all while flying through the sky at 500 miles per hour, by the way. It's so odd when you think about it.

Mankind is really at its best, and worst on airplanes. This has, unfortunately, borne itself out in terrifying ways in the recent past. But even in far more mundane ways, humanity never ceases to surprise and amaze me at 35,000 feet.

On a Spirit Airlines flight home from Ft. Lauderdale to New York I had boarded the flight writhing in pain. I'd been in Islamorada with my family all week for the Thanksgiving holiday and had done something to my back. I was the first to board the plane and take my seat. After a few minutes I realized that making it home without some kind of pain relief was not going to be easy, so I walked to the front of the plane and asked the flight attendant if there was any aspirin or Tylenol on board.

There wasn't, but I was told I had time to deplane and walk to the airport gift shop if I wanted to. In too much pain, I went back to my seat instead, closed my eyes, and tried to relax. A few minutes later, a flight attendant tapped my shoulder, then handed me a bottle of water and Tylenol.

It turned out the captain had overheard our conversation, deplaned, and had himself gone to the gift shop to purchase Tylenol and water for me. I was literally gobsmacked. I thanked him profusely upon deplaning, but it felt inadequate, so later that night I sent an email to customer service praising the captain's extraordinary kindness. After receiving no confirmation or response within a few days, I worried his generosity would go unnoted, but figured there was nothing more I could do.

Until, that is, I received an unsolicited email query from a reporter from Investor's Business Daily. (Working in PR/marketing, I subscribe to a service that forwards reporter queries throughout the day.) She was writing a story on the cost-cutting measures Spirit Airlines takes to turn a profit and was seeking customers with positive experiences despite the cuts...are you kidding me? Ba-bing! Thank you, crazy coincidences. I'm hoping the captain saw this article. Given my experiences on airplanes, stranger things have happened.

What weird or wonderful (or both) encounters have you had in flight? Share your stories below or find/follow me on Facebook.

To find out more about me or my work, please visit wendysimmons.com.

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