This article explores the thematic intersection of gender, social constraints, and tragic individualism through a comparative analysis of Abdulhamid Sulaymon oʻgʻli Choʻlpon’s Kecha va Kunduz (Night and Day) and Gustave Flaubert’s Madame Bovary. Representing Eastern (Uzbek/Central Asian) and Western (French) literary traditions respectively, both novels serve as profound critiques of their contemporary societies. By examining the protagonists, Poshshaxon and Emma Bovary, this study highlights how patriarchal structures, religious dogmatism, and bourgeois provincialism stifled female agency. Despite differing cultural landscapes, both authors portray the female struggle not merely as personal defiance, but as a fatal conflict with an unyielding societal apparatus.