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This essay explores the development of narcissistic vulnerability and manifestations of toxic masculinity in some Chinese males, examining the interplay of cultural, historical, and psychological factors. Drawing on psychoanalytic theories and clinical case studies, the author argues that certain aspects of Chinese culture—such as authoritarian social structures, rigid gender roles, transgenerational trauma, and dysfunctional family dynamics—can contribute to these phenomena. The deprivation of crucial selfobject experiences, vital for a cohesive sense of self, may lead to compensatory performances of stoicism, achievement obsession, and domination that align with toxic masculine ideals. Two clinical vignettes illustrate how these dynamics manifest across different generations, despite China’s socioeconomic progress. The essay conceptualizes toxic masculinity as potentially stemming from developmentally-impeded narcissistic health in some cases, calling for approaches that address core ruptures to guide affected individuals towards greater self-acceptance and healthier relationships. However, the author cautions against overgeneralization, emphasizing that these dynamics may only reflect the experiences of a subset of Chinese males rather than being universally applicable across Chinese culture and society.