There’s an amazing line from the series finale of The Office:

That line so poignantly expresses how I feel about the six months I spent working aboard the Celebrity Infinity — 20 years ago. Pieces of my heart are still on that ship.

After my parents had exited the cruise industry (in spectacular form), the last thing they wanted was for me to go work on a ship.

They would prefer that I had taken a job as Martha Stewart’s stockbroker, Mike Tyson’s sparring partner, or a waiter at whatever restaurant Nicole Brown Simpson was frequenting, instead of stepping aboard a ship.

But I was a few months shy of my 21st birthday.

And I was old enough to make my own mistakes decisions.

In fact, by then, I was an immensely skilled decision-maker. I don’t mean to brag but…

I had gone from a midtown Manhattan management role, to serving grits at a diner in the remote mountains of North Carolina so I could share a secret apartment with my fine, upstanding, 35-year-old boyfriend who was 100% leaving his wife if I could just give him a little more time. 😒

So yeah. I was f*cking great at making decisions.

I knew I needed to leave that loser, and get out of that horrible situation, and the prospect of working on cruise ships gave me something I hadn’t had in a while— 

Options. 🙏

I was a very attractive candidate, and quickly had an abundance of offers.

You’re probably wondering, “How on earth is a 20-year-old an attractive candidate for anything other than a date with Leonardo DiCaprio?” (Sorry, last pop culture reference, I promise.)

Most people from western countries end up on ships because they’re running away from something.

And that’s exactly what I was doing.

So for me, it didn’t matter that Seabourn wanted to discuss an Assistant Cruise Director contract that started in six months, or that Holland America was keen to train me for a Youth Director position.

I needed to escape my situation IMMEDIATELY.

So when Celebrity Cruises asked me if I could fly to Alaska to join the Infinity after a 20-minute phone interview, I packed my bags without a second thought.

And that, ladies and gentlemen, is how I found myself in a low-level “Activities Staff” job with a cruise line I had never even heard of.

I was scheduled to join the Celebrity Infinity mid Alaska-season at their embark/debark port of Seattle. 

They sent me an email with my contract, a plane ticket, a hotel reservation, and a short list of instructions detailing what I needed to pack (certain footwear, buckets of pantyhose, and no less than two ballgowns. Seriously.)

I bid farewell to the dickhead, sold my car, hopped on a flight, and arrived in Seattle the night before the ship did.

As I was dozing off in my hotel room, enjoying my last night on dry land, I jolted in shock as I heard the door handle turn, and watched some lady walk right into my room carrying a bunch of suitcases.

Um.

Who the f*ck are you? And why do you have a key to my room?

It turned out, she had just flown in from the Philippines, and was joining the Infinity as a cocktail waitress the following day.

And she would be my roommate for the night. 😳

A complete stranger would be sharing my hotel room, in a city where I didn’t know a soul, and with literally no on-site supervision from the company.

And they didn’t even tell me. Just let that sink in for a moment.

Thank god she was lovely.

It was an uncanny prediction of what the next six months of my life would look like—

Truly interesting, diverse, and delightful people thrown together in an outlandishly bonkers environment.

The next morning, we woke up and joined about a dozen others who were shuttled over to the Seattle cruise port.

A gaggle of cruise guests were disembarking, while a new flock lined up, ready to set sail on their dream Alaskan vacation.

As I was waiting on the pier, a young woman came bounding toward me with the energy of a million suns exclaiming “Are you Kristin?!”.

When I responded in the affirmative, she gave me a hugely invasive hug and said “give this to Yolie” — then vanished just as mysteriously as she had appeared.

Um. What.

It became clearer when I finally got on board, and was immediately greeted by three smiling faces:

🇬🇷/🇨🇦 Esperanza — my new boss, our “Activities Manager”, a sassy Greek-Canadian who spoke four languages.

🇵🇭 Chanie — my new co-worker, a Filipino dynamo who never seemed to run out of energy.

🇿🇦 Yolandie (Yolie) — my other new co-worker AND roommate, a bubbly and hilariously sarcastic South African, with whom I would be sharing ~100 square feet of personal space for the foreseeable future. 

I told her that I believed I needed to pass on a bear hug from someone, which I then executed with flawless perfection. 

It turned out that the woman on the pier was the person I was replacing, and in the chaos of the turnover, wasn’t able to say a proper goodbye to her dear roommate.

Great start! These folks were super nice, and seemed to really like each other. That was encouraging.

I exhaled, fully expected a few days to settle in, undergo some training, and get my bearings on my new life.

Nope.

Yolandie brought me to the prison cell cabin we would be sharing to dump my bags, then straight to the tailor to be fitted for my uniforms.

I then rushed over to my first team meeting, and met the other two members of our group:

🏴󠁧󠁢󠁳󠁣󠁴󠁿 Alan — our VERY tenured Cruise Director from Scotland, who was quite possibly the long lost sixth member of the Rat Pack, flawlessly blending comedy, music, and old school charm.

🇦🇺 And finally, James — Alan’s heir apparent, a hugely successful radio talent from Australia who, just like me, was on his first ever cruise contract, and escaping a different life back home in Melbourne.

Then I was thrown a microphone, and found myself center-stage in a thousand-seat theater to welcome aboard the guests, and present the first evening of entertainment. 🤯

I quickly met the Band Director and was given some musical cues to follow, shown a mark I had to hit for the spotlight, and just told “Introduce yourself and then talk about karaoke in the Rendez-Vouz Lounge”.

I had only been on board a few hours, didn’t even know where the Rendez-Vouz Lounge was (or even how to find my own cabin), and my ass was itching like crazy because they were forcing me to wear pantyhose.

🎬 The theater filled up.

💡 The lights dimmed.

🎷 The band played “da-da, da-da, da-da, daaaa-da”.

🎤 And I stepped on stage in front of a crowd of a thousand people. 🤯

The spotlight hit me, and I was suddenly blind.

I said something like:

Whew.

It wasn’t great. I was awkward, and got yelled at by the spotlight operator for pacing, but I survived.

My job was to work with an incredible team to facilitate on-board entertainment programming.

During the day, this included relatively tame activities things like:

🤑 Bingo

🧠 Trivia

💃 Dance classes

🏓 Table tennis tournaments

😆 Joke-telling contests

🔪 Ice-carving demonstrations

♂️♀️ Battle of the Sexes (which was my favorite thing to host — I told way too many inappropriate trans jokes that would have gotten me fired these days 😬).

But we only had one job at night—

🎉 We got paid to party.

It was our job to bring liveliness to the public spaces once the sun went down. 

Whether that was getting the dancing started in the Constellation Club, belting out “Love Shack” on the karaoke machine in the Rendez-Vouz Lounge, or doing a round of shots with some half-drunk guests — it was our responsibility to be the life of the party.

Not only was drinking allowed — it was encouraged.

And the shit we got up to in clear view of guests was criminal.

Once the parties were off and roaring upstairs, the real fun started.

And let me answer the question I know you all have:

👉 Yes. We were all sleeping together.

The crew bar was a global menagerie of young, drunk, insecure nomads, seeking validation and belonging.

The romantic relationships were intense and explosive.

The friendships were instant and deep.

And we were all figuring out our place in the world.

I joined the ship to run away from a relationship with someone who –ahem– couldn’t commit.

So it’s unsurprising that when James proclaimed undying love after a mere week together, and asked me to marry him a month later, I agreed.

Celebrity Cruises had stuck gold with me and James.

We were perfectly situated to lead an entertainment department as a Cruise Director / Assistant Cruise Director team. We had management experience, stage talent, programming instinct, and the guests adored us.

But Celebrity was dropping the ball on the most basic shit, and we wouldn’t tolerate it.

I lived off the Pringles they sold in the crew bar because it was logistically impossible for me to eat anything else.

Our schedules were chaotic, and often didn’t align with the crew mess mealtimes (which were far from appetizing, even when schedules did align).

From time to time, we could call a specific phone in the galley, and pray a specific Filipino would pick up, who would then deliver burgers to our cabins at the end of his shift in exchange for whatever cash we had in our pockets.

We called it “renegade room service”, and would inhale it on the floor.

It’s difficult to describe how dehumanizing it feels to be denied food.

So we were thrilled when the HR team led a ship-wide survey asking for feedback on dining. We all energetically vocalized our serious complaints on the availability and quality of food.

The outcome? They hung flags representing the different nationalities of crew members in the mess. Nothing else changed.

Seriously. F*ck HR.

One of the reasons my parents retired from the cruise industry is that the corporations were trying to manage the guest experience from the boardroom.

We saw this too.

Now, I’m not opposed to maximizing revenue. There are plenty of fun ways for guests to shell out extra cash for an enhanced experience.

But the atmosphere shifted from vacationing to upselling.

💉 Our Cruise Director was going under the needle for live botox sessions.

💎 Our activities were getting pitted against revenue events like art auctions and gemstone lectures on the schedule — take a guess at which programs actually got promoted. 🙄

🎤 And our Welcome Aboard Show (which had me shaking in my pantyhose on my first night, but I later adored because it enabled us to instantly connect with the guests) was replaced with a video starring all the people on board who sold shit — not the entertainment team.

Our karaoke machine had been malfunctioning for months. 

It was a digital program where we’d punch in the “code” for the song someone had chosen, and then it would play.

But half the codes didn’t work.

So guests would spend hours working up the courage to perform their favorite tune, they’d nervously get up on stage, we’d pump them up with a killer introduction, hit the code, and…

❌ Nothing. Silence. Awkwardness. 

The party would just grind to a halt, and we were left apologizing rather than running around the room leading a rowdy chorus of “BUM BUM BUM” during Sweet Caroline.

After reporting this issue countless times, we were thrilled when the ship was docked in Miami one day, and the Junior Purser casually mentioned that he had a pocket full of petty cash to go ashore and buy a new karaoke machine.

Yes! Finally!

“No, you misunderstand,” he apologized. “This is for the crew bar.”

The next day, James and I walked off the ship, and never went back.

—

In the few years that followed our departure from the Celebrity Infinity, we lost four dear friends from the entertainment department on board:

Emil — Stage Technician

Igor — Musician

Wes — James’ roommate ❤️

Yolandie — My roommate ❤️

Life is short. I wouldn’t have traded this experience for the world.

Cheers! 🍻

-Kristin :-)