This paper examines Paula Vogel’s approach to sensationalizing social issues such as prostitution in her 1981 play, The Oldest Profession. The paper focuses on analyzing how Vogel explores American culture and history to make sense of the lives of the five elderly prostitutes in the play. We resist empathizing with these elderly sex workers for their old age and their profession. However, this resistance can be overcome, and we feel empathy for them. This is what Vogel calls negative empathy. Vogel stresses the importance of negative empathy as a way of overcoming hatred for different social groups. To achieve this empathic response, the author gives her characters the voice to tell their own stories and demonstrates how their lives are shaped by the culture and history to which they belong. In the play, Vogel specifies how the labor of the five elderly women is devalued and how they struggle to survive in the era of Ronald Reagan in the 1980s in America. The author’s handling of difficult subjects and problematic characters such as geriatric prostitutes gave her unwelcoming criticism from 1970-80’s feminist theatres. Nevertheless, Vogel believes as a feminist playwright, she should give female characters three dimensionalities that would present them as complex as any male character on stage.