Always borrow money from a pessimist. He won't expect it back.

The line is a compact example of epigrammatic humor: it turns a practical maxim (“choose your lender wisely”) into a joke about temperament. A “pessimist” expects disappointment, so—by comic logic—he will not anticipate repayment and thus will be less aggrieved when it fails to arrive. The quip also satirizes the moral economy of borrowing by implying that expectations, not contracts, govern social friction. Although often credited to Oscar Wilde because it resembles his style, the joke functions more broadly as a cynical observation about human psychology and self-fulfilling expectations.