While there are many difficulties faced by world language educators, both teachers and students of certain languages--languages commonly identified with countries and cultures deemed to be hostile to the United States--often find themselves in uniquely paradoxical situations. This article begins with a brief anecdotal description of the personal challenge of speaking a "language of the enemy," and then turns to a discussion of world language education in the United States, emphasizing the distinction between the commonly taught languages (CTLs) and the less commonly taught languages (LCTLs). Next, an overview of linguistic bias in the history of world language education, focusing on the cases of German and Russian, as well as both Farsi and Arabic, is provided, followed by a discussion of the uses of "soft power" in the promotion of a country's language and culture. After a brief analysis of the role of media in constructing images of different languages for public consumption, and the impact of such media efforts on the teaching of some of the LCTLs, the article concludes with a discussion of the fundamental dilemma that we face in teaching what are considered by many Americans to be the "languages of the enemy."