This article explores the masculine images and ideals produced by the love tales of seventeenth-century Korea. Although male characters were undoubtedly represented as vulnerable and passive characters, they were also offered opportunities to represent passionate love. Particularly, the exploration focuses on the configurations of lovesick men with a close reading of Unyŏng chŏn (The tale of Unyŏng) and Sangsa-dong ki (The tale of Sangsa-dong), which provide a model of romance fiction while at the same time exposing desire as it is regulated and expressed through Confucian ideology. At the center of the discussion is the question of the possible political effects of male characters’ romantic experience of “being lovesick”—what does male lovesickness represent, and how do the characters manage to negotiate with cultural norms while reproducing the significance of the male body? I examine the dilemma of male characters pursuing their romantic goals of love and marriage under the frame of lovesickness. Within the confines of Confucian society, which limited relations between men and women, rather than perceiving characters involved in romance as mere victims of love within an oppressive culture, this study reveals the complex negotiations between mind and body, morals and sexual desire, and gender ideals and romantic love.