This ethnographic study explored the health-related concerns, within dating relationships, of 40 female adolescents aged 15 and 16. The results reveal a complex interaction of male/female relational dynamics and socialization processes in these relationships. To avoid behaviours risky to their health, participants had to negotiate power relationships with partners and peers; yet, paradoxically, any increase in their power could increase the threat of violent confrontation, loss of power, and further health compromises. The girls' desire to have a dating partner outweighed their desire to avoid health threats such as substance abuse and violence. This dynamic can be understood in terms of patriarchal power imbalances. These findings point to the gravity of adolescent girls' health issues and the need for interventions that challenge mainstream culture and that foster empowerment among female adolescents.