The present thesis explores the interrelated linguistic processes of grammatical and semantic broadening as they pertain to the Japanese concept of aware during the initial stages of its development, paying close attention to the 250 year span between the 8th and late 10th centuries which saw its highly limited interjectional use burgeon into the diverse instantiations characteristic of the mid-Heian period (794-1185). As I will argue, it was precisely during this time that aware’s literary usefulness as an interjection motivated a crucial syntactic reanalysis into a bound nominal form that was in turn conducive to its subsequent grammatical diversification, semantic strengthening and even aesthetization. Accordingly, approaching this issue from a strictly functional perspective, I aim to link the linguistic evolution of aware to the growing social import and standardization of Heian poetic practices, taking note of the cross-generic influence between poetry and prose and its effect on aware’s path to diversification. After a brief introduction to the literary and cultural background surrounding the history of aware in Chapter One, I turn to its narrow interjective function in the Kojiki (712), the Nihon shoki (720) and the Man'yōshū (759) in Chapter Two, arguing that it was the very markedness of this linguistic realization that enabled aware to diversify in the first place. In Chapter Three, I then focus on aware’s development as evidenced in the Kokin wakashū (905), using the prose-bound tokens found in the Kana preface to explain the semantic incongruities between the overtly analogous structures found in poetry and relating them to the emergence of aware’s bound nominal form. Chapter Four consequently contextualizes the importance of this development with poetic and prose evidence from the Taketori monogatari (c.901), Ise monogatari (c.930) and Tosa nikki (935). Finally, the Epilogue addresses aware’s status at the turn of the 11th century and discusses the overarching connection between aware’s linguistic evolution and its growing aesthetic status.Arts, Faculty ofAsian Studies, Department ofGraduat