The Almost Free Cruise That Almost Was

Last night I got a phone call from an unknown phone number, and because I had 45 minutes before my friend’s storytelling show started, I picked up. An automated voice welcomed me to a political survey. I was about to hang up when the computerized man voice sweetened the deal: “If you answer our 30-second survey, you will receive a free two-night, three-day cruise to the Bahamas courtesy of Caribbean Cruise Lines.”

Partly because I was killing time, partly because I’ve always curious how these “too good to be true” things actually work, and partly because I thought I deserved a relaxing cruise to the Bahamas, I stayed on the line and answered the questions. (Though it ended up taking 90 seconds, I was not offered three free cruises, as I then felt entitled to.) The voice thanked me for my participation and I was asked to press one to be connected to a Caribbean representative to claim my prize. With 43 minutes until show time, I pressed it. I had no idea what I was getting in to, but I’ll give you a hint: It was not a free cruise. 

A woman named Shirley (her name has been changed) picked up, welcomed me to Caribbean Cruise Lines, and thanked me profusely for doing my American duty of answering a political phone survey. If I was the hundredth caller she dealt with that evening, her voice gave no indication.

“What is your name?”


“Can I call you Matt?”

“Absolutely.” Things were going well.

“Can I have your email address, Matt?”

“Sure. M…H…P.”



“Got it…”

“At Gmail dot com.” I was not at all expecting what Shirley said next, mostly because it made no sense:

“Whoa-whoa! Someone’s living fast!”

The fact that Shirley correlated owning a Gmail account with some sort of exciting thrill-a-minute lifestyle was so unexpected and bemusing I still have no idea what to make of it. I like the idea of Shirley imagining me, a Gmail user, in an Aston Martin, my trunk full of priceless stolen art and the baron’s buxom wife in the passenger seat pouring us both glasses of champagne as we weave the hairpin turns of the Monaco coast:

“Darling,” I say through my pencil thin mustache.

“Yes, my love?” the baroness coos into my ear.

“Hand me my phone. I need to check my Gmail account.” I glance at the odometer. We are going 140 miles per hour but with the baron’s Aston Martin, it feels no more than a leisurely 40.

She stiffens. “My maniacally jealous husband has inevitably discovered the theft, we have a plane to board to Switzerland in twenty minutes, and the police have no doubt searched your villas in Paris, Moscow, and Buenos Aires. Rival spies are probably threatening your family, and are piecing together your decades of malfeasance and turncoat activities. Everyone you have ever known and loved may be dead. Why would you want to check your trifling email?”

“Because, dear,” I say through a drag of a my cigarillo, my cashmere scarf flapping indiscriminately in the cool, brine-soaked air. I know she is an assassin sent to seduce and kill me. I knew it before she even did. “Because I am trying to get a free three-day, two-night cruise in the Bahamas, courtesy of Caribbean Cruise Lines.”

Shirley asks me if I’m still on the line, and then asks me where I live. I tell her Brooklyn. She mentions how she used to live in New York, with her sister on Grand Concourse. I’m not really sure where that is, but say, “That’s great!” very enthusiastically. Later I confirm that it’s somewhere in the Bronx, the only borough I have never been to (what I was ever doing in Staten Island is another story entirely).

Shirley launches into her pitch, and even though she may be reading off a script, she totally makes it her own. When she gets to the onboard casino, she mentions that if I hit it big at bingo, I should not forget who helped me book my cruise. I laugh, and I imagine she has only ever said this to me. A fast-living Gmail man like me is no stranger to lady luck.

The offer keeps getting better. I have 18 months to book my cruise from the time I accept the offer. All entertainment and food is included. Shirley tells me that I will be sailing on the newest Caribbean cruise ship that is literally a floating resort. I will have access to a personal concierge 24 hours a day. She keeps asking me little questions to make sure I’m engaged and uses my name constantly, like, “Does that seem good to you, Matt?” and, “Do you like complimentary live comedy shows, Matt?” The answer is always yes.

There is something that Shirley keeps on mentioning, and that is just how, exactly, Caribbean Cruise Lines afford to be so generous with this offer. After all, I only listened to four questions about President Obama and punched four numbers and I’m being treated to a three-day, two-night floating buffet.

“We think the best way of advertising is through word-of-mouth. Do you know why that is?”

“Because you trust the person telling you, because you know them.” I feel like I’m being quizzed, and I want to impress Shirley.

“You’re absolutely right. I like a man who has things figured out,” Shirley says. I start to wonder if I would rather have Shirley in my Aston Martin rather than the baroness. To my knowledge, Shirley doesn’t want to kill me. At least not yet.

At this point in the conversation, I’ve interpreted the familiarity of Shirley and her kindness as a tacit approval that by being one of the few people brave enough to answer questions and stay on the line, I have scored a free cruise.

After listing the impressive amenities that my free cruise will entail, Shirley mentions the costs I must incur. She frames it as costs that Caribbean Cruise Lines can’t avoid—a customs tax levied by the federal government. She quickly explains I’ll need identification, to avoid lingering on the money.

“Do you have a passport or signed birth certificate?”

“I have a passport.”

“Wow! Look at you!” There isn’t a trace of irony in her tone. Between my Gmail account and passport, I am leading quite the rock and roll lifestyle.

“Love, do you have my passport?” I ask the baroness. We are on a large yacht, sailing for the North African coast where I have a private plane waiting. The police had cleverly scuttled our Swiss itinerary.

“Which one? You have nine different versions in your valise,” she says as she frantically looks through my bag, looking for my secret notebook, no doubt, but she won’t find it there.

The memories of my past false identities waft through my mind on cool Mediterranean air. “Glenn Vanderloon” to get into East Berlin in the early 80s, “Sergei D’Ambrogio” to fund the revolutionaries in Panama years later.

“The American one, dearest,” I say from the captain’s deck. “Jack Lawrence, I believe.”

She is flustered, and her mascara has begun to fade. “What does it matter which one?”

“I need it to get on my free three-day, two-night cruise to the Bahamas,”


“Courtesy of Caribbean Cruise Lines,” I finish over her interruption.

“But we’re already on a beautiful yacht, perhaps the most beautiful vessel in all the world.”

I gaze out over the vast sea, knowing in twelve hours we will find her terminal in the dusky Tunisian evening where I will enjoy a fine cigar and decadent meats. “Yes, sweetheart. But this one doesn’t have complimentary live comedy shows.”

Back in the real world, Shirley launches back into how Caribbean relies on word of mouth for advertising, and how she’s confident I’ll recommend Caribbean to everyone I know and even give the cruise line repeat business myself. I have six minutes until my friend’s show. I’ve been on the phone for quite some time. She casually asks for my credit card number.

“I’m not comfortable giving that information over the phone,” I say.

“It’s completely safe. Your credit card company will not issue any funds without a verbal confirmation from you.”

“I don’t see why you need it right now, especially if I have 18 months to book.” A noted art thief and international conman can’t be too careful.

“It’s like if you were going to pick up a pair of Jordans at Foot Locker because they were 50% off during a promotion. They wouldn’t let you say you were going to come back in six months and get them for the same price. This $59 charge is to show your interest and reserve your room sometime in the next 18 months.”

“I’m still not comfortable,” I say, unable to combat her very logical reasoning. Where was suave Sergei D’Ambrogio when I needed him?

Without batting an eye or ever breaking her meticulously polite and amicable tone, she says, “Let me see if I can help you out.”

I am put on hold. Shirley is doing me a solid, subverting the system to get my free cruise. During this brief time to myself, it occurs to me that perhaps the political survey was a red herring. Would my opinions really be factored into a Time graphic or was it all just a set up, to make me feel patriotic before signing up for the ultimate American vacation? Just as I start to piece things together, I’m on the line with a manager.

“Hello this is Tim (name changed). I heard you had some questions about using a credit card over the phone?”

Tim’s voice is very polite but it’s a little more worn, perhaps because he doesn’t get to butter up potential clients but has to deal with the skeptics. He assures me it’s 100% safe. His voice is kind, and I almost believe him.

“Shirley says your from Brooklyn,” he says, and I can tell from his voice it’s not because he’s trying to angle me into payment but because he’s generally bored in his South Florida call center.

“I’m originally from Massachusetts, but now I live in Brooklyn.”

“I grew up in Brooklyn. Where do you live?”

“Clinton Hill,” I say in a slight white lie. I do technically live in Fort Greene, but literally a block away from the border.

“Oh, I grew up in Brownsville.” Tim says.

I know Brownsville is not a great area of Brooklyn, or at best, it’s remote from the bright lights of Manhattan. And I’ve never even been to the Bronx. And here I am, just $59 away from a free cruise that I don’t need or deserve. My dreams of luxury are ludicrously based in Monaco and Aston Martins and baronesses with generous cleavage. Through a 36-minute phone call for a free cruise, I’ve learned more about myself than any phone survey ever could about White House fiscal policy.

“This call is being recorded, and your bank will get a copy of this for security purposes. This is absolutely safe,” Tim reminds me.

His voice is so comforting, so assuring—I want to believe him, but something feels off. Like the fact that he claims he would send a tape of this conversation to my bank, or that hundred dollar cruises would just be given away to people burning time until a storytelling show. My mother once made me print out, read, and summarize the entirety of eBay’s terms and agreements before letting me use her credit card online. I was eleven years old and I didn’t even win the bid, making the whole explication de texte an exercise in futility, but a hard-earned lesson. How far had I strayed from her anti-scam teachings. With my wits about me, I backpedal.

“Sorry, I’m just not going to buy anything tonight. Thank you for spending all this time with me,” I say to Tim.

“Have a good night.”

“You too.” I hang up the phone. It’s two minutes until my friend’s show, and I’ve got a lot to think about. I don’t doubt that I could have booked a cruise, but there are undoubtedly sneaky charges or a mandated eight hour shift in the bilge room snuggled into the fine print would make any deal far from free. Shirley and Tim aren’t the master thieves–they are likely watching the clock as closely as I am, me until my friend’s show and those two until they can go home and stop foisting a predatory too-good-to-be-true promotion on unsuspecting housewives and bored twenty-somethings. Somehow, this makes me feel far worse than assuming Shirley and Tim are running a con out of a garage in Boca Raton. I hope they aren’t paid on commission. My fast Gmail life provides no comfort or conclusion: All is quiet somewhere in the middle of the dusky Mediterranean. My friend’s show is quite good.


Matt Powers lives in NYC. 



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