Traveling solo on a cruise ship sounded cinematic in theory..
In practice, it was daunting.
I didn’t know what to expect long hallways, couples everywhere, the quiet hum of being alone in a crowd. I braced myself for that familiar solitude. But the universe, once again, had other plans.
It started with a Karen.
Not a Karen — but a Karen who, with perfect accidental timing, said: “Our group is full. You can find another group to go for dinner with“.
And just like that, on the very first night, I found myself sitting down to dinner with ten perfect strangers.
Conversation flowed as if we d rehearsed it. No awkward silences. No polite small talk. We laughed, shared stories, lingered. After dinner, someone suggested karaoke. Then dancing. Then more dancing.
This wasn’t a group killing time this was a group choosing the moment.
At the first night karaoking, I had no business singing. You already know this. History has proven it.
But somehow, I ended up doing a duet.
“I Got You, Babe.” Sonny and Cher.
My partner was the Harley Angel –the angel sent to be my courage, and, as I would later learn, had biggest heart on the ship. The song turned out to be prophetic. That was exactly what we became for one another.
We got you, babe.
Over the two weeks, this accidental gathering turned into something solid a support group disguised as a cruise dinner table.
There was the Facilitator Mama Bear, our unofficial compass. She cruised often, knew every venue, every shortcut, and gently herded us across the ship like a benevolent cruise director.
There was the 90-year-old soul in a 28-year-old body –a chemical engineer who casually mentioned she blow things up with household items. I treated her with appropriate fear, especially after she threatened me if I ever put her name in for karaoke.
There was the Lost Hart, quiet and introverted, who we eventually coaxed onto the dance floor a small victory that felt enormous. And later, a Shenanigan group graduate.
There was my Cruise Dad solo cruising while celebrating his wedding anniversary. I started introducing him as my father, which became a running joke. People constantly asked where my dad was. I’d say he was old and needed sleep. He’d fire back that he’d have my pajamas laid out when I got back.
There was the Zen Chef, our food advisor and culinary conscience.
There was the World Traveler from Alaska, heading to Alaska –because of course.
There was the Pickleball Detective, endlessly searching for a pickleball court and for someone to join him in the hot tub.
There was the Dancing Princess, who would always be the first up to dance and honoured us with her birthday cake.
There was the Quiet Architect, somehow balancing work and cruising/traveling and making me quietly wonder if I could have done my life’s journey differently.
And then there were the two Babas — grandmas — Baba C and Baba P.
They were at karaoke, looked at me on stage, and whispered, “What is he doing up there?”
But they stayed. They cheered. They joined our group.
They showed me something quietly profound: travel does not have an expiration age.
Baba C, especially, became my sunshine. Days later, she was the only other person I could convince to step up to the mic with me.
We sang “You Are My Sunshine“.
It wasn’t polished. It wasn’t meant to be. It was honest. And it was enough.
The group became a moving unit. Luca, the Italian guitarist, became our musician and we showed up every time he played. Dinners together (despite the logistical nightmare of finding tables for more than eight). Group photos that broke the cruise gallery’s rules. Wandering Skagway and Hakodate. Halloween haunted house. Glow and costume parties –Audrey Hepburn incarnate beside me as a zombie fresh from the dead in the Halloween contest losing to Hermione Granger (even though we had an insider as a judge).
There were margarita bar runs. Late-night Reuben sandwiches. Beta testing version 2.0 of my message game. The birth of the Shenanigan Club, knocking on doors to remind early sleepers they were missing out. Signs mysteriously appearing on cabin doors, courtesy of my inner prankster.
But more than the antics, there was safety. This group let me sing loudly, badly –without caring how many imaginary wine glasses I shattered. They listened intently to each other. They cheered in supportive ways.
For the first time in a long while, I wasn’t performing despite fear. I was performing because I was held.
Saying goodbye was harder than I expected. There were tears –real ones. The kind you don’t explain away.
I didn’t board that ship looking for a support group.
But I left knowing something important: If I’m going to step onto a stage one day, I don’t have to do it alone.
And maybe –just maybe– this was the confidence boost I didn’t know I needed to begin.
