As tax season approaches, some people become desperate to find tax deductions in order to limit their tax bill. CNN reports that a lawyer from New York tried to deduct a prostitute’s “services” as medical expenses.  In all, he attempted to deduct $65,934 for the prostitute and almost $5,000 for pornography and sex therapy books and magazines.  The Tax Court found that theses deductions were improper and therefore not deductible

Anything Illegal, No Matter How Much You Paid For It, Cannot Be Written Off

This is a pretty simple rule, don’t do anything illegal.  If you do (such as buy drugs), don’t try to write it off in your taxes.  Heck, if you make a deal with your drug dealer for a certain amount of drugs, you pay for your drugs, but you don’t receive your drugs, you still can’t win a lawsuit against the drug dealer.  You could have a written contract between you and the drug dealer notarized by Charlie Sheen and a court still wouldn’t find in your favor.

Weird But Legal Tax Deductions

One of the most commonly cited “weird” tax deductions is for pet food.  However, before you start trying to write off all of Fido’s expenses, the tax deduction was only allowed because the business used a cat to help keep away rodents and insects.  The other odd tax deduction was for body oil for a professional body builder.  How far this tax deduction would go is unknown.  Could a person who goes tanning constantly in order to appear more attractive on YouTube be able to deduct those expenses?  It’s doubtful.

Many times a person will attempt to write off a business meeting or business lunch/dinner.  While this is fairly common, some people have taken the business meeting to extremes.  One man took his entire family to Hawaii on a private jet to celebrate his daughter’s Sweet 16 birthday party.  He claimed that since he ran a “mom and pop” shop that this expense should be tax deductible.  The court promptly disagreed upon seeing the photos of the family vacation.

What type of tax deductions have you tried to get away with?