In the current study, we investigated the developmental dynamics between positive youth development, being bullied in adolescence, gender, and sociocultural risk factors. Participants were 3,509 males (49%) and 3,656 females (51%) studied longitudinally across the ages of 9, 13, and 17 years in the Growing Up in Ireland study. Using structural equation modeling, we discovered that being bullied in early adolescence was most strongly predicted by having fewer close friends, higher family poverty, and living in neighborhoods with higher levels of disorder. However, the social disadvantage of a young person's school did not impact being bullied. More positive reports of connection and caring in early adolescence were negatively predicted by neighborhood disorder and family poverty, and being female had positive association with relationships with teachers. Developing confidence, competence, and character in late adolescence was notably related to having fewer experiences of family trauma and transitions in childhood and to having higher levels of rapport with parents in early adolescence. The results highlight the importance of studying relationships and psychological development in sociocultural context.