A lawyer from New York kept track of his visits with prostitutes in a journal and tried to deduct their "services" as medical expenses.
The whopping $65,934 may have tipped off the IRS to a problem.
He also attempted to deduct nearly $5,000 for pornography and sex therapy books and magazines.
Unfortunately for him, the United States Tax Court found that the payments he made to prostitutes were illegal, and therefore not deductible.
As for the porn, the court ruled that "those amounts were incurred for petitioner's general welfare, not pursuant to a doctor's prescription or for a specific medical condition."