This study sought to explore the direction of sympathy education in the teaching of modern poetry. Sympathy is a long-discussed concept, but it is still a subject of exploration in that it has different definitions in different areas. Sympathy is also a complex concept with cognitive, emotional, and communication elements, but, generally, previous studies have discussed Sympathy from a specific point of view. In this study, Sympathy was defined as a value evaluation based on the discussion of M. C. Nusbaum. Nusbaum contradicted the preconceived notion of emotion as an irrational recognition and presented the importance of emotion as rational judgment. The study also noted that in Nusbaum’s view, Sympathy deals with various emotions through any narrative imagination that understands the specific life of others, as revealed in literary works. Accordingly, this study defined Sympathy as a value-evaluation and, in teaching modern poetry, the development of narrative imagination is necessary for Sympathy education. The narrative imagination of modern poetry was regarded as a process in which the reader actively reads the life form of the poetic speaker. In order to present the specific direction of Sympathy education in teaching modern poetry, Lee Yong-ak’s works, which are suitable for developing narrative imagination, were selected for analysis. In light of the above, the direction of Sympathy education was proposed in two ways: “acquisition of one’s status as an observer through compassion” and “building an Sympathetic relationship by accepting heterogeneity.” This study is significant in that it has explored the concepts of Sympathy that can be pursued in literary education.