For the two years I was going to Harvard, I flew Toronto to Boston, Boston to Toronto, Toronto to Boston, Boston to Toronto, over and over and over again. The flight was just under two hours, and it was always on a plane with no middle seats. Just a long row of two seats on one side of the plane and a long row of two seats on the other.

So I always had one seatmate beside me.

Somehow that length of trip and style of plane often led me into an intense conversation with the person I was sitting beside. And I do mean intense. Like, the kind of conversation where the stranger beside me has tears in their eyes and whispers something like “It’s time I got serious about my weight” or “I really need to see my son. He’s not going to be young much longer.”

Does this ever happen to you?

I think that happens to a lot of us.

On a shorter flight, it’s not worth the investment. We’re up, we’re down. Who’s got time for a deep chat? And on an ocean-crossing flight, forget it. We brought books to read, slides to build, emails to catch up on. We made eight hours worth of plans. It’s like “I’d love to chat, but I’ve got crap to do.”

But if the length of the flight is jusssssssssst right and the seating layout is jusssssssssst right, your airplane row can turn into a little confession booth in the clouds.

Because when the conditions are right, we feel free to be ourselves. We aren’t trying, we aren’t putting on a face, we aren’t aiming to grow this relationship into anything. We both know the whole thing ends with a two-second “Seeya!” in a couple hours. I don’t know you, you don’t know me, we will never meet each other’s families, we will never meet each other’s friends.

What a load off!

And yet we have each other all the same.

Lower stakes, less judgment, no baggage.

Makes for great chats in the sky.

Sharing with strangers.

One night on my Boston to Toronto flight, I made a strong connection with a bald, bearded consultant in his mid-forties. As he munched peanuts, we slowly inched our way into a discussion on love, relationships, and life.

Near the end of the flight, I said to him, “So… can I ask… what were your first impressions of me?” I just felt like those are so hard to get, and I had a sense that because we were being so honest, he’d tell me the truth. He dished them out straightaway.

“Well, you looked like a stuck-up kid,” he said. “You had your earplugs in, your laptop ready, so I was thinking, Oh great, it’s someone who’s going to quiz the flight attendant about the menu and then ask to see a list of ingredients in the hummus.”

We laughed and had a fun bonding moment, but I avoided asking for his name or for a business card so as not to shatter our fragile, anonymous intimacy.

Soon the flight was landing. Lights dimming, fasten seat belt ringing. Window shades pushed up revealing sparkling high-rises against a darkening blueberry sky. It was a modern sitting-around-the-campfire moment, just missing the crackling logs and chilly breeze off the lake.

I’m not sure what compelled me, but I turned to him and said, “Listen, man, we’re never going to see each other again, but I felt a connection with you. So if you want to tell me anything, just to tell me, knowing that you’re never going to see me again, for the sake of you, I just want to let you know, as your temporary friend, I’ll be listening and happy to receive it. I know that’s really weird, but I’m only putting it out there because I felt a connection.”

And he said, “Whoa… uhhh… wow… well… Jesus… well, you know I’m married, right? And, uh, well, I guess… I guess I just don’t know… if it’s right.

“I guess I just don’t know… if I should be.”

I was trying super hard not to show any emotion and just receive whatever it was he was saying even though in my head I was thinking, “Oh noooooo,” so I just said, “Yeah… yeah… I understand, I mean, yeah, tell me…”

And he said, “This is gonna sound so bad, man, but I gotta tell someone. I know this sounds horrible, but I… I think I’m smarter than her. I feel like that’s the most terrible thing to say. It’s just, I feel like we’re not connecting. I feel like I can’t be with someone who doesn’t get my jokes, isn’t interested in the same issues I’m interested in, doesn’t want to see the same movies. So, like, it’s a big deal! But I think the root of it is that we don’t have an intellectual connection.”

Pause.

Big pause.

“That’s hard,” I said.

And he nodded. “Yeah, sorry. I, I, uh… thank you.”

He crumbled back into his seat and I felt a titanic emotional release emanating from this guy. Like some thick piece of rusted metal, dripping in blood, had finally been yanked out of his stomach after being in there for years. Those words had been wedged deep, forever lingering, forever squishing around, and suddenly they were ejected… and now they could be tossed into a tin pan beside the operating table to be properly examined under bright lights.

His thoughts moved forward a step… and it seemed like he suddenly had a brand new field of thoughts to explore.

The plane skidded to a stop on the runway and we said goodbye before grabbing our bags and walking off the plane.

It was a deep airplane conversation and a beautiful moment, and I figured that was the end of that.

…but then…

…a year later…

…I saw him again.

As I said, I took that flight a lot. So I was getting off the plane in Boston, and there he was! The bald, bearded consultant waiting to walk on to the same plane!

We weren’t going to be on the same flight this time, but I was about to walk right by him.

He looked right at me, and I looked at him. And when my face was a couple feet away from his face, I looked right into his eyes and could see he was stricken.

Like he was seeing a ghost.

He looked afraid.

And I immediately had the sense that he’d decided to stay with his wife. That he had buried his feelings deep or maybe by processing them had been able to see them in a new and more positive light. Maybe he realized he was wrong. Maybe he stayed with her for the kids. Or the money. Maybe he saw more complexity in the problem.

Whatever it was, I felt in that fearful stare that he was thinking something like “Oh no, here is that guy I told that horrible secret to… and though I wanted that secret released and disappeared and blown away, now that horrible secret is still alive and real and exists.”

Part of the deal of the confession he had made was my promise that we’d never see each other again. And now, here I was, seeing him again. Violating that promise.

His scared eyes, tightening jaw, and stiff body language told me I should keep my mouth shut, walk past him quickly, and disappear as soon as possible.

So that’s what I did.

And now I really have never seen him again.

So…

Why did I tell you this story?

What does this mean for you, for me, for us?

Well, I’ll tell you what it means.

It means we all need contemporary confession.

It means that in our loud and chaotic world we need a place to let our thoughts clarify, congeal, and then fall right out of us. We get so bottled up. So tightly wound! We replay pains and problems so often, letting them swirl and spin inside us like tornados, that sometimes those pains and problems start feeling like who we are rather than simply what we’re working through.

That slippery slope can cause us to stay at the bottom for a lot longer than we need to. We slip, spin, and get stuck there tormenting ourselves.

But there is a way out.

A little path to awesome.