It’s fair to assume that most of us don’t enjoy doing taxes—especially if you're self-employed and have to fill out 9,000 forms, keep mountains of documents, and decide exactly which expenses you're allowed to write off. On the latter front: If you’ve spent any reasonable amount of time combing through the Internal Revenue Service website or chatting in person with a rep at your local H&R Block, you’ve probably felt the sting of deduction confusion.
As a music journalist, I’ve had people advise me, "You should keep track of every vinyl record you buy and every gallon of gas you spend driving to a concert." I’ve also been told, in no uncertain terms, not to poke that particular hornet’s nest. (To my credit—and possible financial detriment—I’ve always played it safe.) But some people brazenly go for it, requesting to write off any and every expense that feels even tangentially related to their work.
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Influencer wedding
With that in mind, what are some of the strangest, craziest write-offs people have attempted? To start answering that question, I consulted a real tax pro. Logan Allec, a CPA and owner of tax relief services company Choice Tax Relief, noted that his company works with "a lot of small -business owners who haven’t filed taxes in years." As a result, Allec says they’re "extremely aggressive" with their deductions to minimize penalties and interest, and they "often have to draw the line with them in a stern way."
The "craziest" (or at least "largest") deduction attempt he can think of was on behalf of an "influencer client who landed a large brand deal." As part of said deal, "she had to use certain products manufactured (and provided to her at no cost) by the brand at her wedding and post a certain number of social media posts featuring these products."
"Somehow, she got the notion that—because she did a few product placements as part of a brand deal and had her photographer take some nice photos of these products that she could post on social media—her entire $75,000 wedding was deductible," Allec said. "Yes, she wanted to deduct the catering costs as meals and entertainment, the venue fee as rental expenses, and various other expenses as supplies. My team and I had to explain to this individual that her wedding was overwhelmingly personal, not business-related, in nature, and that the most we would be comfortable deducting was a pro-rated amount of the photographer's fee based on the number of product placement photos over the total number of photos she got in her package."
Wild. But there's more—I also plunged down a Reddit rabbit hole looking for some additional answers to round out this story. Here are four other notable responses:
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"Strip club costs"
In a thread focused on the "strangest expense" tax pros have been asked to write off, one user wrote, "I was working at the IRS, and the guy I was auditing had taken clients to a strip club. I actually allowed the expenses since he met all the requirements of 274, and entertainment was 50% deductible at the time." (We assume that by "274," they’re referring to this. We can’t say for sure.)
Matchmaking
Another Redditor said a client had a "match.com expense" listed among their office supplies. Probably stretching the textbook definitions just a tad. "Client was sitting there with girlfriend, and I laughed and said must have been before you guys got together," they wrote. "It was not—they’d been dating for 5 years. I told him it was not a write off, which was the least uncomfortable part that conversation."
Johnny Cash
Given the above subheading, you might expect that this to involve someone in the entertainment business—or perhaps some big-shot executive taking a potential client out on the town. Not quite. "When I was a tax auditor MANY years ago (>50), I had a minister who deducted his trip to see Johnny Cash in concert as an entertainment expense," someone wrote in a thread about the "dumbest" deductions tax pros have encountered. "His justification: he wanted to see if he behaved like a Christian on stage."
A very, very nice car
I don’t pretend to be a tax expert, so I’ll defer to the Redditor who took issue with writing off "a 250K Ferrari, used exclusively for business purposes." They added that they have this request in writing, still framed on their desk. "They sent a fax response about it, and I didn't care enough to ask why the f—- they thought it was reasonable," they wrote. "I’m sure they had a lovely story for it. Partner didn't wanna push back and signed off on it. Life umm, finds a way."
Now that you've read about bizarre tax stories, you might as well check out our recent piece about the "funniest," "weirdest" things realtors have encountered while showing houses.
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Representative Image: Money changing hands. 
Representative Image: It seemed like a great tip at first. 
Image Source: Reddit | 
Image Source: Reddit | 
Image Source: Reddit |