For mature masculinity to develop, boys and adolescents need nurturing and guidance by both males and females; one without the other is insufficient. In the process of developing mature masculinity, a boy must understand and develop friendships; learn his place in the family by observing the other men and observing role models; learn to interact with the women in his world and understand the messages the women send about how to be a man; monitor and regulate their expression of emotions; and establish a personal set of values to direct his life, seeking to balance the child’s individuation and his place and role in the family. The article briefly examines the theories of Freud, Adler, and Erikson. It then presents an alternative model of male development. This model describes the adult males who are important at various stages of a boy’s development: nurturers, role models, initiators, mentors, and elders. In addition, it describes five stages leading to wholeness--cognitive, conformist, conscientious, autonomous and integrated--that correspond to those five teachers.