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The 12 Craziest Things People Have Tried to Expense at Work

Sometimes truth is stranger than fiction when it comes to the things folks claim are "business expenses."

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business with credit cards and wallet on office desk blue background top view9dream studio/Shutterstock

Nice try, not gonna fly

Depending on your line of work, it’s possible you’ve had to expense some unconventional items here and there for perfectly legitimate reasons that look very strange on paper. In other cases, you’ve been on the receiving end of those expense reports and have spotted some doozies listed by employees trying to get away with some interesting forms of “entertainment” on business trips. This list might sound like something from an episode of The Office, but these are real expenses that were either accepted or rejected by finance. Unlike fudging your expense reports, these 16 strategies will build trust with your boss.

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Nice thoroughbred horses in the stable door

Hay is for horses

When your job is fashion editor for a magazine, you find yourself picking up some pretty interesting photoshoot props. For one particular setup that took place on a ranch, Jane F. of Venice, California needed to keep the inhabitants happy. “I expensed carrots for horses,” she recalls. Fortunately, the finance department didn’t question that one after a brief explanation. Looking ahead to tax time, check out these deductions you can’t afford to miss.

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Shopping basket with grocery products on grey table against light blue backgroundNew Africa/Shutterstock

A real supermarket sweep

“We had a person who worked in advertising sales who bought gift cards for gourmet baskets to give to clients, but then used them for her groceries,” says a department manager for a publishing company who wished to remain anonymous. The sneaky sales rep got away with the scheme for a period of time before the jig was up. Find out the 14 secret signs you may be getting fired.

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Alcohol bottles on a bar with a sexy quilted red backgroundBUY THIS/Shutterstock

Just plain wrong

While working with a particularly rowdy team, Tara R. found herself facing an expense report from a group of employees that seemed seriously suspect. “They tried to expense strippers…and they masked that as booze, which they also couldn’t expense,” she says. Needless to say, that expense wasn’t accepted. Keep these office party etiquette tips in mind the next time you’re celebrating with your colleagues.

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Geometry set with compass, ruler and protractorKenishirotie/Shutterstock

We’re all for education but…

Those school supply lists can be lengthy, and one dad decided his company should foot the bill for the whole thing. “I noticed one employee had an exceptionally long list of office supplies expensed one month, including things like a protractor and graphing calculator,” says Francine C. of New York. “It was basically everything his kids needed for that school year. I would have been sympathetic if I didn’t also know much he makes!” These are a teacher’s best tricks for buying back-to-school supplies.

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close-up of quarter dollar coin on the one hundred Dollar billShipov Oleg/Shutterstock

For whom the quarter tolls

“I worked for a flashy guy with a $2.5 million house and we shared an assistant. He was considered far more important than me,” remembers Suzie L., a lawyer in Florida. “I needed help one day but our assistant said she was busy. She was expensing out a single 25¢ toll receipt for him. He submitted a receipt for…25¢.” Apparently rich people never waste their money on tolls—of these 13 other things.

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Flat lay composition with accessories for cat on color background. Pet careNew Africa/Shutterstock

It’s the cat’s meow

When Jane F. wanted to score a great deal on a photoshoot location, she increased her chances by gifting the property manager (who happened to be a nun!) a cat toy for her beloved feline. “She did cut me a great deal,” says Jane, who said the money guys in her office did allow her to expense the toy. These 12 rules to becoming a master at persuasion can help you get what you want.

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Philadelphia, Pennsylvania, May 19 2018: Spanx store sign entrance with vibrant red, pink color display in PhiladelphiaHelen89/Shutterstock

Spanx a lot

As a Hollywood publicist of more than 20 years, Tiffany M. has had to expense her fair share of items requested by talent. Among the more memorable items? Spanx for an actress who came to a photo shoot ill-prepared. “She was asked to bring her own foundations and ignored the request,” says the flustered flack. “I had to run out and purchase a bunch of different styles and sizes of Spanx because she wouldn’t give us a straight answer on what she needed. I love Spanx but I’ve never spent so much on them in my life. Thankfully accounting was understanding—this had happened before.” Learn about the 25 bad bosses you would never want to work for.

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Top view hand drawn Christmas greeting cards with envelope and Christmas decoration.AngieYeoh/Shutterstock

More naughty than nice

The holidays are a hectic time of year and it isn’t out of the norm for employees to attempt multitasking at work to get things done efficiently. However, one employee took it a little too far. “The company I work for has a policy that if you work through lunch, they will pay for your meal,” says Holly K. of Ohio. “I had one employee submit an expense for her family’s personalized Christmas cards. She said she had been working around the clock and had to design and order them during her lunch break and would rather we pay for those than her actual lunch. I had to explain that’s not the way this works.” Find out the 13 social media posts that could get you fired.

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Close up of orange flavored starburst fruit candyPablo Buenos Diaz/Shutterstock

That’s a lot of fruit flavor

While on a business trip, one executive sent an assistant out for five bags of a specific candy—Tropical Starburst. The flavor was non-negotiable, they had to be the tropical variety. After scouring drugstores and markets for the sugary squares, the assistant was told to put the candy on her expense report. It got bounced back, leaving the assistant on the hook for $20 worth of Tropical Starburst until a different higher up learned of the situation and paid her back personally. Meanwhile, this is the most popular candy the year you were born.

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Close-up top view of comfortable yellow flip-flops isolated on yellowLightField Studios/Shutterstock

If the shoe fits

A theme park publicist found herself in a pickle when a high profile actress came for a visit wearing four-inch heels. Needless to say, the actress was miserable in her ill-advised shoes and the publicist was forced to look for more comfortable footwear. The only thing she could find in her size were a pair of cartoon-themed flip flops. So, yes, the publicist was forced to expense a pair of SpongeBob Squarepants flip flops on her next report. These 20 secrets amusement parks won’t tell you about saving money could have come in handy.

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Toxin injection in Green apple by syringe. Genetically modified food (GMO). Botox injection. Aesthetic medicine. Medical background concept.Tanyastock/Shutterstock

Putting the best face forward

“One of our executives was moderating a panel at a big industry event and thought she could expense her Botox injections,” says Melody F. of Connecticut. “She went so far as to have her assistant file the expense, which we promptly denied. The executive insisted it should be covered by the company so she could represent us looking her best. Still denied.” Perhaps she should have stuck to maximizing her business casual wardrobe.

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Student pencil bag or pencil case with school supplies for student on white background. Blue pencil box with school equipment for math class isolated on white background. School math equipment.ShutterStockStudio/Shutterstock

Time to get schooled

Trying to find a good work-life balance is tricky for everyone, particularly parents. One mom tried to expense her son’s math tutor, saying the company owed it to her because she couldn’t be at home to help him with his math homework herself. While her intentions were good, tutoring is not on her company’s list of acceptable expenses—but, hey, what a suggestion for a work perk! Speaking of, these 15 secret company work perks will make you jealous.