During the twentieth century, the principle of good faith in contractual performance has been developed into one of the most important maxims of American as well as German contract law. This development, however, seems to have increased rather than decreased academic disagreement about the function, meaning, and limits of good faith. The discussion seems to be locked into a group of inescapable dilemmas which frequently reappear as typical, but unsatisfactory parts of academic discourse and judicial opinions; namely, the controversies between arm's length bargaining and contractual altruism, between judicial arbitrariness and equitable flexibility, and between judicial law making and judicial restraint. The goal of this essay is to gain deeper insight into this observation. It attempts to show that both branches of the debate, the American as well as the German, rely on a relatively small set of stereotyped arguments which typically appear in ordered pairs of diametrical oppositions such as those mentioned above. The main thesis of this essay is that understanding this structure implies a new assessment of the cogency of typical argument patterns deployed in theoretical and doctrinal statements on good faith. Many arguments contained in such statements appear as convincing or even compelling only because they are presented in contextualized form, i.e., tailored to the problem at hand and omitting their typical counter-arguments. The model developed in this essay, however, leads to an understanding of legal arguments as less demanded by a particular problem within the doctrine of good faith, as well as more open to attack by their legal counterparts, than they usually appear to be in the practice of legal discourse. This essay, therefore, also has implications for the rationality of that discourse.