In fact, the tax code allows for quite a bit of creativity. Some deductions depend on your ability to tell a good story. Others defy logic. Your challenge as a taxpayer is to know how some of these strange rules apply to you, or how to bend the facts so you qualify for the deduction.
Medical expenses provide plenty of gray areas.
For example, your doctor tells you that it's time to lose some weight. So you hire a personal trainer. You go to your accountant and present your cancelled checks as a medical expense. She asks you whether the weight-loss program was done to treat a specific illness. No, it was just for general good health.