Filing taxes can be stressful, confusing, and sometimes even a little funny. Every year, people look for ways to lower their tax bills, and some get creative—maybe too creative. The IRS has seen it all, from the reasonable to the downright bizarre. Why does this matter to you? Knowing what not to claim can save you from audits, penalties, and a lot of headaches. Plus, understanding the weirdest tax write-offs can help you spot mistakes before you make them. Here are some of the strangest things people have tried to write off on their taxes—and what you can learn from their missteps.
1. Pet Food and Care
Some pet owners have tried to claim pet food, vet bills, and even doggie daycare as tax deductions. The logic? Pets provide security or emotional support. While the IRS does allow deductions for service animals or guard dogs used in a business, your family cat or goldfish doesn’t count. You might have a case if you run a farm and your dog guards livestock. But for most people, pet expenses are personal, not business-related. Trying to write off your pet’s kibble could get you flagged for an audit.
2. Bodybuilding Oil
Some professional bodybuilders have tried to deduct the cost of body oil used in competitions. Their argument is that the oil is necessary for their job, making muscles look more defined under stage lights. The IRS, however, usually sees this as a personal grooming expense, not a business necessity. It’s not deductible unless you can prove it’s essential for your trade and not just for appearance. This example shows how important it is to separate personal and business expenses.
3. Weddings and Honeymoons
A few couples have tried to write off their entire wedding or honeymoon as a business expense. The reasoning? They invited clients or discussed business during the event. The IRS doesn’t buy it. Unless your wedding is a legitimate business event, like a conference or seminar, those costs are personal. Even if you talk shop at the reception, it doesn’t make the whole event deductible. If you’re unsure, ask a tax professional before claiming big personal events as business expenses.
4. Inflatable Pool Toys
One business owner tried to deduct the cost of inflatable pool toys, claiming they were for entertaining clients. The IRS denied the deduction, saying the toys were for personal enjoyment. If you run a business that hosts client events, you can deduct some entertainment expenses, but they must be directly related to your work. Pool toys for your kids don’t count. Always keep receipts and document how each expense relates to your business.
5. Cat Food for Pest Control
A junkyard owner once tried to write off cat food, arguing that the cats kept rodents away from the property. In this rare case, the IRS actually allowed the deduction because the cats served a clear business purpose. This is an exception, not the rule. If you want to claim an unusual expense, be ready to prove it’s necessary for your business. Keep detailed records and be honest about your reasons.
6. Private Airplane Rides
Some people have tried to deduct the cost of private airplane rides, saying they were for business meetings or client visits. Unless you can show that the flight was strictly for business and not for personal travel, the IRS will likely deny the deduction. If you mix business with pleasure, only the business portion is deductible. Document your itinerary and purpose for each trip.
7. Cosmetic Surgery
A few taxpayers have tried to write off cosmetic surgery, claiming it was necessary for their job. For example, an actor or model might argue that surgery helps them get roles. The IRS rarely allows this unless the surgery is directly related to a medical condition or injury. Purely cosmetic procedures are almost never deductible. If you’re considering this, consult a tax expert first.
8. Home Swimming Pools
Some people have tried to claim the cost of installing a home swimming pool as a medical expense, saying it was prescribed for exercise or therapy. The IRS has allowed this in very limited cases, such as when a doctor prescribes swimming for a specific medical condition. But you need strong documentation, including a doctor’s note and proof that the pool is used mainly for medical reasons. Otherwise, it’s considered a personal luxury.
9. Gambling Losses
Gambling losses can be deducted, but only up to the amount of your gambling winnings. Some people try to write off all their losses, even if they didn’t win anything. The IRS keeps a close eye on these claims. If you gamble, keep detailed records of your wins and losses.
10. Fake Clemencies
Some taxpayers have tried to claim donations to fake or non-existent charities. The IRS checks the status of organizations, and if your “charity” isn’t registered, your deduction will be denied. Always verify that a charity is legitimate before making a donation or claiming it on your taxes.
What These Weird Write-Offs Teach Us
The weirdest tax write-offs show how creative people can get when trying to save money. But they also highlight the importance of understanding what counts as a legitimate tax deduction. The IRS has clear rules, and stretching them can lead to audits, fines, or worse. If you’re ever in doubt, keep good records and ask a professional. It’s better to be safe than sorry when it comes to your taxes.
Have you ever heard of a strange tax write-off or tried to claim one yourself? Share your story in the comments.
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