It was an epic trip with some excellent people — and, inevitably, some jerk.
We left for Jamaica on Feb. 17 on an early flight — our first trip without our three boys, Liam, Landon and Levi.
I had a plan: propose to my now-fiancée Alanna (she said yes) in some sort of grand and romantic fashion. Easy, right?
Not so much.
Planning romantic gestures is not exactly a male strong suit. For weeks, I ran through ideas in my head. I could write it in the sand. I could do it at a fancy steak dinner.
Nothing felt right. Everything seemed a little too predictable.
Then the light bulb finally went off.
Alanna’s favourite movie of all time is “The Wedding Singer,” for the scene where Adam Sandler serenades his girlfriend on an airplane with help from Billy Idol.
What if I did that?
The idea sounded great — until I realized the logistical nightmare of actually pulling it off. Alanna isn’t easy to fool. If I suddenly wandered off to talk to ground staff or the flight crew, she’d immediately suspect something.
So I did what any shameless man would do: I pretended I had stomach issues.
Multiple “urgent” bathroom trips later — much to her chagrin — I managed to sneak away to the departure gate. The problem was, we were too early and no staff were there yet.
Eventually I tracked down a customer service desk, where they told me I’d have to speak directly with the flight crew.
So I waited. And waited.
Of course, we had moved seats closer to the gate, which made sneaking away even harder.
Finally I spotted someone who looked like part of the crew disappearing behind a pillar. My chance.
I jumped up like it was an emergency and hurried over, explaining my plan: I wanted to sing “Grow Old With You” from the movie and propose on the plane.
The woman was a ground crew member and said she’d pass the message along.
Back to my seat I went.
I didn’t see her again until we were boarding. She caught my eye, I hung back while Alanna continued ahead, and she told me the flight crew knew the plan and would take my guitar up front.
That part wasn’t suspicious. I bring my small guitar on flights fairly often.
But Alanna immediately noticed I had fallen behind and asked why.
Thinking quickly, I told her the crew said I needed to check the guitar up front.
That explanation didn’t go over smoothly.
In true Irish fashion, she pushed back immediately and said to just bring it to the seat. I didn’t want to argue too much — the last thing I needed was her figuring everything out.
She already suspected a proposal might be coming. We had done things slightly out of order — baby first, house second — so the next step wasn’t exactly a mystery.
Without realizing it, she was unintentionally sabotaging my plan at every turn.
At that point, I still hadn’t spoken directly with the flight attendants and was starting to wonder how this was actually going to happen.
But when we boarded, they gave me a look.
And I knew they knew.
It’s remarkable how much humans can communicate with a simple glance.
We found our seats and, if you’ve seen “The Wedding Singer,” you’ll know it was absolutely imperative she got the window seat.
One of the attendants came over shortly after and said they needed to take the guitar up front. Perfect.
Alanna resisted again — saying we normally just put it in the overhead bin — but this time I quickly handed it over before she could derail the plan again.
During the flight I made a few more strategic “bathroom trips” to coordinate with the crew. We decided the moment would come after the first service.
Finally, the time arrived.
The flight attendants cleared the aisle, quietly moved the passenger sitting beside us, rushed through the water service — and then came over the intercom in Billy Idol fashion.
“We have a special announcement for one of our economy passengers in seat E26,” they said.
And I was off.
I walked down the aisle, belting out the song as loudly as I could over the roar of the engines, locking eyes with the woman I want to spend the rest of my life with.
Alanna hates being the centre of attention. But in that moment, she didn’t mind.
I told her how much I loved her, handed her the ring — and she gave the answer I was hoping for.
“Of course I will.”
We kissed, the entire plane burst into applause.
It all happened to quickly, and suddenly the flight didn’t seem long at all.
The crew even gave us a congratulatory card and comped our champagne.
And, selfishly, I felt relieved I wouldn’t spend the entire vacation nervously waiting for the right moment.
It was perfect.
Mostly.
Because a couple of days later we ran into something else entirely.
We met plenty of wonderful people during the trip — everyone was excited for us and genuinely kind.
Then a group of rowdy Americans arrived.
This happened the day after Canada lost to the U.S. in Olympic hockey, so they started with the predictable chirping about the game.
We congratulated them. That’s what Canadians do.
But after a few drinks one of them decided to escalate things.
He loudly announced that Canada would be “the 52nd state soon anyway — along with Greenland.”
Joking about sports is one thing. Joking about invading sovereign countries is something else entirely.
One Canadian nearby spoke up.
“You know, that’s actually really rude and hurtful.”
And suddenly a whole group of Canadians — myself included — joined in.
We reminded them that the last time our countries went to war, Canadians burned down the White House.
His friends went quiet. He turned red. A crowd of Canadians had gathered.
Eventually he apologized, but he didn’t speak to any of us again.
And honestly, that interaction stuck with me. Because it felt like a small metaphor for something bigger.
When Canadians are polite, we’re very polite.
But when someone crosses a line — disrespecting our country, our neighbours or basic decency — Canadians also have a backbone.
A stronger one, in fact, than many people seem to assume.
And it reminded me of something important.
Kindness isn’t weakness.
But push Canadians too far, and you’ll find out very quickly that politeness has its limits.
