Escalating health care costs are affecting patients across the country. As employers and insurance companies face higher expenses, they may move to a cost-sharing strategy, which potentially increases financial burdens on patients. In this situation, physicians may find themselves serving as both medical and financial advisors for their patients. Clinical encounters in which patients experience financial hardship can be awkward and frustrating for both parties. Physicians must learn to discuss issues of affordability in a manner that builds, rather than detracts, from a therapeutic alliance. This article describes our experiences using several communication skills that can help in the discussion of health care costs with patients. The primary skill, empathic communication, which includes “we” statements and “I wish …” statements, serves to create a platform for shared decision-making, negotiation, and a search for alternatives. In addition, it is helpful if physician offices have resource materials available and strategies identified to assist patients facing financial hardship.