This paper draws on the available literature, as well as unpublished data, to reconstruct the often chaotic early childhood experiences of homeless adolescents and to describe the problematic ways of relating that may result from these troubled life histories. We also examine the processes by which homeless youth become separated from their families, and we make connections between socio-emotional problems on the street and early neglect and abuse at home. The risk-amplification model is offered as a theoretically compelling explanation of the adolescent homeless experience, high rates of victimization on the streets, and mental health problems that arise out of these circumstances. Finally, we present a promising approach for intervening with homeless youth, one that explicitly targets this cycle of ineffective interpersonal relationships.