Unlike the separation-based, stereotyped views of boys’ developmental movement into adulthood, this paper will argue that there are more modern and relational models, as well as multiple pathways, for young males to journey through such rites of passage. Indeed, it will be suggested and supported by both qualitative and quantitative data that the more classic models depend on a “boy code” of traumatic separation from mother and the feminine, a process that is not only negative rather than positive in its developmental trajectory, but also likely to create a premature traumatic separation, leaving boys at risk for emotional maladjustment, everyday sadness, increased incidence of depression and the potential for violence toward the self, suicide, as well as violence toward others. More-positive visions and versions of male rites of passage will be posited and described. The definition of emotional “resilience” during this significant period will be re-addressed as one of “healthy vulnerability,” sustained through connection to loving adults, rather than a classic belief in stoicism and release from relational ties. Attachment theory will be brought to bear and the desperate yearnings of adolescent males not only for connection to adult mentors, but also for non-romanticized friendships with adolescent females, will be discussed. Finally, the understanding and substitution of these new, more positive, developmental pathways will be linked to the prevention of violence.