The problematic features of teaching philosophical ethics are inextricably linked to, and are dependent upon, the problematic features of philosophical ethics itself. This thesis is exemplified by two radically diverse approaches to searching for the good and the good life. The differences within each approach are discussed in terms of the principles of Plato and St. Augustine, on one hand, and William James and John Dewey, on the other hand. Before introducing their thoughts, attention is given to a context of teaching ethics to collegiate students, that is, to a structure or framework within which to organize and to interpret the development of principles in the history of ethics. I have concluded that differing conceptions of the good require correspondingly differentiated modes of searching for the good, both of which must be considered in teaching ethics in the collegiate classroom.