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My Dream Job Is To Be A Jet Ski Rental Guy Down In The Caribbean

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Yeah, I’ve actually had multiple orgasms on jet skis. Maybe it’s something in our blood that we can just, you know, get hard from riding fucking badass, you know, terrain vehicles, water crafts.

– Kenny Powers

You surely rolled your eyes and scoffed at the title while simultaneously wondering if you accidentally stumbled onto one of those lifestyle websites that litter your newsfeed from every girl you went to high school with that cuts hair for a living at Great Clips. I get it, Christina, you want to come across as cultured. It’s just hard to take you seriously with the “34 Reasons You Should Spend Your Life Traveling” when the most exotic place on your resume is Wildwood, New Jersey. Fortunately, my intention is not to connect and “relate” to that target demo.

Now, you might have higher ambitions like working at your dad’s firm or moving up the corporate ladder on the sheer combination of coming from a favorable genetic pool and an undeniable surplus of charisma, but that’s just not in the cards for your boy. If I followed in my pop’s footsteps, I’d be a third-generation water treatment operator in suburban Philadelphia, and I have the looks of a Ben Roethlisberger cardboard cutout that was left in the rain for too long, so my options are extremely limited. Factor in that I have no redeeming skills and the work ethic of an overweight Frenchman and I’m practically useless. With that said, I’d still very much like to be a contributing member of society, and I think my true calling is to run a wave runner rental and tour guide business in the Caribbean.

I’ll get down to the shack on my modest plot of beach each morning in the same raggedy bandana, salt water stained shades, aggressively short swim trunks, sun faded tank top, and sand-filled flip flops that I’ve been rocking for the better part of the last decade. Got a loaded schedule for the day with the Costello family booked at 10:30, the Montgomery honeymoon couple at 2, and a late evening run with the Greenbergs at 7. Thankfully, my trusty employees, Rameriz and Suarez, have already put the jet skis on the water, full tanks of gas and all.

Early beach goers’ interests start to pique, and several walk-ins blindly sign rental forms and liability waivers while dropping a cool hundo for an hour. That busty coed who’s having trouble fitting her jugs into a lifejacket? “Let me be of some assistance.” That same voluptuous señorita can’t climb onto the water craft minutes later? “I can give you a boost.” She’s having problems with the simple start-and-go dynamics of the vehicle? “Let me show you the ropes.”

Once too many reckless, adrenaline-filled jokers start to hit the water, I’ll grab my whistle and patrol the crystal blue ocean, moderating and keeping the riff-raff to a minimum. Sure, part of me wants to see that 13-year-old punk splat his head on the dock trying to spray his older, legal, smokeshow of a sister, but that’s not good for business, and I’d be out a jet ski. So I’ll give him a stern warning via blow of the whistle and throat-slashing motion, console the girl, and offer to take her out for drinks and a late night private ride on the open sea.

With extremely lax, some would say, lawless environment down in the islands, I’ll be perpetually sipping on whatever rum concoction I think of that day. This will keep me sharp and on point for tours where I’ll be expected to do what I do best: bullshit. “Yes, St. Martin’s was discovered in 1912 by nudists looking to escape persecution from the puritan pro-clothes society of their time.” If someone calls me out on the outlandish statements I preach as cold hard facts, guess who’s going to the back of the line. I simply don’t have time for you to question my credibility. Do I look like Chris Broussard?

After a day of bending Mother Nature over and leaving chumps in my wake, I’ll help beach and lock up our money making machinery with los dos amigos. The day will be capped off with a celebratory spliff, and I’ll proceed to go to the nearest resort bar looking for some estranged middle-aged tail to spend the night with. Lather, rinse, repeat.

Sure, it might not be the most honorable or respected existence — up-charging the fuck out of vacationers and banging desperate housewives who were only there to save their crumpling marriages — but someone’s got to do it.

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Dan Regester

Dan Regester @Dan_Regester is a Senior Writer, Podcast Host, and Video Guy for Grandex Media. He's Delco trash to the core and a UCF cinema studies graduate because he never got around to applying to an actual film school. Dan is a gambling man, crypto investor, and procrastinator. He enjoys long walks to the water fountain between bench press sets and is not a fan of the homeless, the elderly, or the Phoenix Airport. Email tips to

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