In Melville’s Moby-Dick, there are significant but inexplicable instances in which its narrator Ishmael records “strange feelings” he experiences but fail to account for why they haunt him. Critics have failed to investigate why Melville composes such scenes and what their meaning is in terms of the notorious thematic complexity and profundity of Moby-Dick. Such peculiar emotive moments, Melville indicates, suggest the fact that feelings, especially strange feelings, are a key to unveiling the secrets of human agency and its cognitive and affective capacities. Melville, I propose in this presentation, is deeply concerned with the secretive role and functions of feelings and therefore depicts the particular moments of strange feelings both Ishmael and Captain Ahab undergo in similar ways. Melville’s aim is to reveal the truth that feelings are not opposite to reason as is generally believed in Western philosophy but fill in the gap of rationality of perception. Indeed, in Moby-Dick Ishmael and Captain Ahab are collectively described as problematic characters whose perceptual faculties are not necessarily subject to their reason. Therefore, they cannot but go through paradoxical moments of subjectivity and even crisis of selfhood. Moreover, the two main characters oftentimes experience the mysterious working of strange feelings when they struggle with the interlocking questions of self, agency, and affect. In Moby-Dick their existential struggle and crisis are indicative of what Melville’s contemporary philosophy and literature overlook and thus fail to explain: the necessary service of strange feelings for linking individuals to reality. By examining how Melville philosophizes such a new dimension of feelings in human agency, I suggest Melville’s Moby-Dick not only challenges the contemporary conception of the superiority of reason over feeling but complicates the ontological significance of strange feelings. Melville’s attention to strange feelings in Moby-Dick, I argue, foreshadows affective psychology and neuroscience that restore the importance of feelings in understanding humanity and reality.