Cutting across the disciplines of trans gender studies and psychology, this book examines the psychological decision-making process behind twenty-three Malaysian trans men’s journeys navigating masculinity from childhood through adulthood. Using interviews and grounded theory methodology, the author analyses how trans men reclaim and redefine a form of resilient masculinity that seeks to divorce itself from patriarchal definitions, done through the exploration of relationships with their identities and de-linking male identity from masculinity. The book examines how trans men redefine their masculinity while maintaining proximity to femininity. Trans men unpack expectations of masculinity from Malaysian perspective on race and gender, to centre their decision-making on their own values and beliefs.