This chapter explores the unique intersection of masculinity and financial therapy, offering practitioners a trauma-informed, attachment-based, and gender-aware framework for working with men. Drawing on psychological research, clinical insights, and real-world case studies, the chapter examines how traditional gender norms, such as self-reliance, emotional restriction, and provider identity, shape men’s financial beliefs and behaviors. It highlights the relational impact of these norms and provides therapeutic tools for engaging male clients who may resist emotional vulnerability or help-seeking. Practitioners are invited to examine their own internalized assumptions about men and money and to adopt interventions that balance validation with challenge. Through diverse case studies, the chapter addresses topics such as financial control, shame, gendered relational conflict, and the influence of religious and cultural scripts. It concludes with a call to move beyond rigid gender binaries toward a more holistic, humanized understanding of men’s financial lives. This chapter equips financial therapists, planners, and allied professionals to support men in rewriting their financial narratives with agency, empathy, and relational depth.