This book investigates the origins and evolutions of gender benchmarking in Asian literature. It examines how various agents such as ritualistic practices, family expectations, cultural orientations and even dogmatic factors contribute to the benchmarking of gender as presented in Asian literature and its adaptations. This allows exploration of relevant notions in demonstrating the rooted causes, developments and changing aspects of cultural norms and how they act upon men and women as individuals in the familial, social and vocational contexts. This book provides a systematical analysis on the representation of gender in terms of various historical backgrounds, geographical territories and cultural products in the Asian context. It connects cultural conventions and literary works written centuries ago with digitalized modernity through diagnosing the circumstances that give rise to the emergence of gender norms, their persistence, decline, and reappearance. Through this, it raises questions about the millennial influences and effects of Confucian ideology upon some Asian cultural products. It also dissects gender-related biases and discriminatory acts in the ancient setting across the contemporary digitalized environment to provide a contemporary response towards concerns over gender-related shaming and ostracization. Finally, it discusses the fluidity of gender, the varying perceptions of this idea and the existence of gender itself—from cyborg literature to artificial intelligence applications. This makes it an ideal all-in-one reader for intellectuals and students in gender studies, Asia-focused humanities, and comparative culture and literary studies.