This article comparatively examines Ali Dashti’s “The Story of That Night” and James Joyce’s “The Dead” through the lens of the crisis of masculine selfhood. Its central question is how two narratives built around a similar situation, namely a man’s confrontation with a woman’s emotional past, arrive at two fundamentally different horizons of meaning. The study adopts a qualitative, comparative close-reading method and draws on concepts such as masculine narcissism, the idealization of woman, the collapse of the imaginary order, and the relation of love to memory and death. The findings show that in both stories, the woman initially appears not as an independent subject but as a mirror for stabilizing masculine identity and as an object onto which male desire and fantasy are projected. Once the woman’s past is revealed, this constructed image collapses, and the man is forced to confront the limits of his perception and the fragility of his identity. Yet the two protagonists respond differently. In Dashti’s story, the crisis leads to jealousy, hatred, pessimism, and psychological closure; in Joyce’s, it opens onto shame, reflection, and a form of existential revelation concerning love, time, and death. The study concludes that, despite their structural similarities, the two works articulate distinct modes of masculine confrontation with otherness and human limitation.