Rephrase: you can probably get away with cheating on your spouse, but the IRS will always catch you.
Case in point, Mr. Walter Halby who attempted to reduce his tax liability by claiming medical expense deductions for his patronage of prostitutes. Mr. Halby claimed $100,000 in deductions for payments to prostitutes as necessary treatments for medical conditions (sexual addiction and erectile dysfunction). I’m not a doctor so I won’t comment on whether feeding an addiction is a proper course of treatment for any type of addiction, but Mr. Halby failed to take the “treatment” part of the allowable tax deduction for medical expenses into account. Mr. Halby was never diagnosed with a medical condition that needed treatment, nor did a doctor prescribe a specific course of treatment for Mr. Halby. Even more unfortunate for Mr. Halby, he failed to keep adequate records of his payments for his “treatments”, didn’t show that repeated sexual gratification was necessary to cure his “illnesses,” and he lived in the wrong state. Prostitutes normally don’t give receipts or invoices, so Mr. Halby couldn’t substantiate his payments or reasons therefore. Most unfortunately for Mr. Halby, paying for sex is illegal in the state of New York. You can’t deduct a payment for medical treatment if that treatment is illegal. If Mr. Halby lived in Nevada he may have had a better case.
