This study is one of the first to examine the narrative links connecting social change, contested gender norms, body image, and eating disordered practices among southern Italian women. The research is based on 16 months of fieldwork, and I compare and contrast the stories of 23 educated women in southern Italy to highlight the contentious realities of entering adolescence in conservative social contexts where gender relations and value systems are undergoing rapid transformations. I examine how these young women dealt with conflicting cultural expectations of womanhood and whether it affected their emotional, psychological, and physical well-being. Their stories shed light on how parental control, community surveillance, and conflicts in developing gender identities and maturing womanly bodies contributed to their emotional distress. Distressed young women used rebellion and manipulation and control of food and the body to negotiate unjust social relations, specifically gender relations, that delegitimized their selves and, in some cases, their bodies.