How One Sneaky Supervisor’s Hawaiian Dream Trip Turned Into a Petty Paradise Lost
Hawaii. Sun. Surf. Umbrella drinks. For most, the word conjures images of paradise. For one overbearing supervisor named Tom, however, his trip to the Aloha State became a masterclass in petty office revenge—served up with a side of 90s-era travel sabotage that would make even the most creative HR rep raise an eyebrow.
Let’s set the scene: you’ve worked almost 15 years at a company, earned your stripes, and have a yearly tradition of attending a work conference in Waikiki with your buddy. Enter Tom, a new supervisor who’s equal parts nosy, obnoxious, and eager to bask in the reflected glory of others. When Tom’s sneaky ambition threatens your hard-earned Hawaiian getaway, what’s a seasoned employee to do? If you’re Reddit user u/xboxgamer2122, you fight fire with a little creative mischief.
The Office Intruder: Tom and the Art of Annoyance
Every workplace has a Tom. He’s the guy who rifles through your papers, “borrows” your work, and then takes credit for your ideas—always with a toothy grin and a whiff of self-importance. As u/xboxgamer2122 recounts, Tom didn’t technically supervise them, but he made a habit of peeking at documents left unattended and distributing them to his own team, all while acting like the king of collaboration. “It was the sneakiness...that irritated me,” OP admits, echoing the shared frustration of countless office workers everywhere.
But Tom’s real crime? Crash-landing into the annual Hawaii conference tradition, meant as a reward for years of dedication. When limited conference funding meant only two could attend, Tom used his rank to muscle in, forcing a literal coin toss for the coveted spot. OP won—but this was just the beginning.
Petty Revenge, 90s Style: Travel Tricks and Sabotage
If you think modern travel is a logistical nightmare, commenters like u/CatlessBoyMom and u/FlyingAce7 are quick to remind us that the late 90s and early 2000s were the Wild West of reservations. With just a name and a flight number, you could call airlines or hotels, tweak bookings, and even change someone else’s travel plans, no online verifications or 2FA in sight. As one top commenter put it, “25 years ago things were less secure. The good ol’ days, when bothering to do a little bit of work you could have a disproportionate amount of fun.”
Armed with years of travel know-how, OP pulled off a subtle act of sabotage: after confirming their own (upgraded!) First Class seat, they called the airline and moved Tom’s reservation to a different day, then canceled his hotel room at the sold-out resort. All it took was a pay phone and a bit of insider knowledge. As OP clarified in the comments, “Exactly. Name and Flight Number would do it back then.”
Tom’s Hawaiian Meltdown: From Business Class to Last Resort
What followed was a symphony of petty justice. On flight day, Tom—having failed to confirm his reservation—wound up stuck in a dreaded middle seat in coach, while OP sipped drinks in First. Tom’s rage was palpable, ranting up and down the aisle, demanding a seat swap (“I politely declined,” OP deadpanned), and blaming the airline for “messing up his reservation.” Redditor u/rainman_95 summed it up: “For that personality type, you definitely ruined the trip for him. Nicely done.”
But the real kicker came at check-in. With the resort fully booked, Tom’s reservation was gone—leaving him with a ten-minute trek to a motel offsite. His attempt to share OP’s room was met with feigned ignorance (“Sorry, only one bed!”). The schadenfreude in the Reddit comments was strong: “The deliciousness of this exceeds my lunch right now. Well done!” wrote u/ConfidentSea8828, while others suggested even more devious ways to foil nosy coworkers in the future.
The community, however, was divided. Some cheered the poetic justice (“Most excellent tomfoolery,” quipped u/CoderJoe1; “LOVE this!” gushed u/catincal). Others raised an eyebrow at the collateral damage: “Kind of sounds like you ruined the days of a lot of innocent bystanders in the process,” noted u/Icy-Pea-4789, pointing out that hotel and airline staff bore the brunt of Tom’s fury. Meanwhile, a few questioned the ethics: “This is a petty revenge I can’t agree with...did you not meddle with the travel agent just trying to do their job?” mused u/Sorels.
Lessons From Paradise: Office Petty or Justified Justice?
So, is this the ultimate tale of justified workplace payback, or did OP take things a step too far? The answer, like the best stories, depends on your perspective—and perhaps your proximity to a Tom of your own. As u/ashen_crowbar brilliantly observed, “He’ll probably spend years blaming ‘airline incompetence’ instead of his own ego. Chef’s-kiss level pettiness.” And as OP’s friend Bert later joked, this act of revenge “kinda made up for not being able to travel together.”
A few commenters even offered practical advice for future skirmishes with nosy office types: why not leave bogus paperwork out for Tom to find, or “special” documents designed to get him tangled in red tape? (u/MotherGoose1957 and u/OkBath4021 had a field day with this idea.)
In the end, OP’s story is a nostalgic blast from a less digital, more mischievous era—a reminder that sometimes, in the battle of the workplace, a little creativity can go a long way. Just be careful who you trust with your travel details.
What’s Your Pettiest Office Revenge?
Have you ever gotten back at an obnoxious coworker—or had someone pull a fast one on you? Share your stories in the comments below. Whether you’re Team OP or think the line was crossed, one thing’s for sure: the next time you leave your paperwork out at the office, you’ll think twice!
Aloha, and may your next conference trip be drama-free—or at least, First Class.
Original Reddit Post: Hawaiian Resort