This paper explores and highlights the importance of social, cultural, and behavioral contexts in the effectiveness of mentoring relationships. A first section looks at growing up in American and the varieties of personal and social development that are found. This section argues against viewing adolescents as similar across the boundaries of location, community, and culture. A following section examines how youth form an identity and find a personal self and a social role. This section notes that in making the separation from the childhood bond to parents, adolescents need the supportive presence of other caring adults. The next section discusses developmental and environmental stresses involved in growing up due to parental difficulties, poverty, minority status, and the absence of agreed-upon standards of child and adolescent well-being. This section details the consequences of these stress factors for adolescents in terms of delinquency, drug abuse, school failure, and other negative outcomes. In a section on social support systems, the roles that community, parents, and schools can play in assisting adolescents to cope with the challenges that face them are explored. A penultimate section reviews models of helping, discussing the effectiveness of some approaches over others. A final section argues for making connections and building a facilitating environment. Eleven references are included. (JB)