The ship rocked in the waves as I stared down at my glass of wine. I knew I had a choice to make. We had been at sea for just a few hours, and it was already clear that I only had two real options for survival. I could spend the week blackout drunk by the pool — relying solely on margaritas for sustenance — or I could hit on the cute jazz singer who was serenading my aunt with a John Legend song in the ship’s lounge.

I hadn’t considered the familial headache I’d have to endure when I accepted a last-minute invite to go on a Caribbean cruise for my grandparents’ 60th anniversary. But thus I’d been harangued by my grandparents about the horrifying fact that I was unmarried at the ancient age of 27, and my aunt kept making comments about the frizziness of my hair, refusing to accept that this is just what happens to curls in humidity. If this was what the rest of my trip was going to look like, I knew I had to come up with a plan to stop me from jumping overboard.

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I glanced around the lounge and honed in on the boyishly handsome, blue-eyed singer. He was the only other person in sight who was under the age of 40. I decided that seducing him would be my lifeboat.

He wrapped up the song and gave my aunt a wink. Before I could make my move, though, two of the most beautiful people I had ever seen walked up to him. A statuesque blonde — with a supermodel body poured into a bandage dress — gave him a kiss on both cheeks, as did her equally stunning beau, a chiseled Fabio-type wearing a purple satin shirt with a few too many buttons undone. Through thick Eastern European accents, they congratulated him on his set; he replied that he was looking forward to their own show the next day. These perfect humans, I realized, were performers on the ship.

I finished off another glass of wine and decided to join their conversation. To my surprise, the singer and the other two performers — who I learned were aerialists in the cruise’s musical theatre productions — were almost excessively friendly. They invited me to join them for a drink on the ship’s upper deck, where their guitarist friend was playing.

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The aerialists and I took shots of vodka and swapped stories about where we were from. I complained about the subway and my fear of being priced out of my beloved Brooklyn neighborhood. The golden couple were Ukrainian; as they told me about the conflict in Crimea, my New York problems seemed petty and minuscule in comparison. The ocean breezes rushed by, and the female aerialist (who, unsurprisingly, was a former Bolshoi ballerina) ordered us another round of shots.

Young performers sign their lives away to cruise ships for months at a time, hoping to hone their craft and get the experience necessary to land jobs on Broadway or the West End, I learned. They rehearse for weeks before coming aboard, and they spend their days hopping from beach to beach and evenings performing in flamboyant revues. Then they get wasted and fuck each other, but somehow still manage to wake up early the next day to hit the gym.

The blue-eyed singer was off in the corner chatting with a gaggle of well-dressed girls who sported heavy eye make up and enviable tans. I looked them up and down — my competition for the night. The aerialists caught my dirty looks and told me that the girls were actually musical theatre performers on the ship. “But you must watch out,” Fabio warned me of the singer. “He is a whore.”

The ballerina slapped Fabio’s arm. The singer was recently heartbroken, she said. He signed up for a six-month cruise contract with his ex-girlfriend, another stunning performer in her early twenties. They had met on their last cruise and decided to sign on for another contract together again. But almost as soon as the ship set sail, she dumped him for another guy on the boat. He was making his way through dancers and whiskey to mend his broken heart.

“You cannot hook up with him even if you want to,” the ballerina continued, looking me dead in the eyes. “There are cameras everywhere on the boat, and if he gets caught with you, they will kick him off. They kicked off one of our friends before.” She told me how the ship keeps a close eye on its performers, and the minute employees step out of line, doing something as innocuous as kissing a passenger at her state room door, the cruise line terminates their contracts, kicks them off the boat at the next port and refuses to hire them again. So while they’re encouraged to be friendly with passengers, the performers have to stay on their best behavior at all times.

The warning put a damper on the evening. I finished my drink, promised my new friends I’d meet up with them the next day after their show, and staggered back to my room.

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I spent the next several days touring the Caribbean islands with my family by day, indulging in four-course meals in the ship’s dining room, and meeting up with my new friends by nightfall. The next time I saw the singer, I had returned to the boat after a day at the beach on St. Croix, and met my grandparents in the lounge. At this point they were besotted by him, too, since he happily played Frank Sinatra songs at their request. With the seduction tabled, I decided there was no harm in continuing to innocently flirt with him. He was too charming to ignore and I had a few more days to kill.

The aerialists and I met at the roof deck after their show, which featured Barry Manilow songs and dancers clad in bikinis and pineapple hats. The guitarist and his fiancée, a British dancer with cat eyes and Targaryen hair, joined us at the bar. We talked about life below deck. Couples working on the ship could request to live together, they told me, but the tiny rooms usually come with two twin sized beds and look eerily similar to dorm rooms, making cohabitation at sea more of a nightmare than a vacation. I wondered if that’s what broke up the singer and his girlfriend.

I ran into the singer at the ship’s Vegas-style martini bar one night and coaxed him into meeting me in St. Thomas the following day. “Whatever happens on land, stays on land,” I said to myself. But much to my dismay, half of the ship ended up going to the same beach, and we spent the day snorkeling in the clear water and laying together in the sand, surrounded by suburbanites in oversized t-shirts who recognized him as the on-ship celebrity that he was. I was frustrated that my fellow passengers had unknowingly cockblocked my romantic rendezvous, but I decided not to let it spoil the experience. Meeting these performers was satisfying enough, since they transformed my boring family cruise to the reliving of spring breaks of yore.

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But after a week, I had realized that I wasn’t cut out for the spring break-esque sea life. I gained seven pounds as a result of my diet of alcoholic and shrimp cocktails, and it wouldn’t be long before I was thrown back into my real life. Which was probably for the best: the constant hangover was starting to wear on me.


Lisa Ryan is a writer in Brooklyn. She likes Tim Hortons and aspires to brunch with Amal Clooney. Follow her on twitter: @lisarya.

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Flygirl is Jezebel’s new travel blog dedicated to adventures big and small, tips and tricks for navigation, and exploring the world at large. Have a story or an idea? We’re always taking submissions; email us with “Flygirl” AND your topic in the subject line. No pitches in the comments, please.