This chapter introduces the concept of brittle financial health as a clinically underarticulated yet culturally pervasive condition among men. This concept reveals the fusion of financial control with masculine identity under conditions of emotional suppression and performative stoicism. Drawing on behavioral finance, masculinity studies, trauma psychology, and narrative identity theory, brittle financial health highlights the silent crisis of male financial distress, one that is not marked by a visible dysfunction but by an overregulated facade of competence that conceals psychological fragility. Brittle financial health sits at the intersection of identity, finance, and emotional containment and is not theorized as a pathology. Rather, it is a survival-based posture shaped by gendered socialization, institutional roles, and internalized scripts of provision and control. This chapter builds upon existing financial therapy models by moving beyond gender-neutral assumptions. It then proceeds to provide a reframed, masculinity-competent framework grounded in Nassim Taleb’s theory of antifragility, retooled for clinical and behavioral application. Through an analytic synthesis of empirical literature and conceptual innovation, the chapter delineates the mechanisms by which male financial distress is misdiagnosed, culturally silenced, or behaviorally misread. It offers a structured model of antifragile financial identity based on identity diversification, behavioral elasticity, and temporal anchoring. In doing so, it lays the groundwork for a new paradigm in gender-responsive financial therapy, one that neither pathologizes masculinity nor romanticizes vulnerability. An antifragile approach to financial therapy for men aims at supporting men through psychological volatility with structural coherence, linguistic legitimacy, and narrative reconstruction.