Building on evidence that romantic experiences are associated with depressive symptoms in adolescence, we examined their bidirectional association, as well as the role of sexual activity and parent-adolescent stress in their association. Data were collected from 71 early adolescent girls (M age 13.45 years; SD = 0.68) and their primary caregiver initially and one year later. Results indicated that adolescents who engaged in more romantic activities experienced increases in depressive symptoms over time. Second, greater depressive symptoms predicted romantic involvement and sexual activities, including intercourse, one year later. Third, dysphoric adolescents who were experiencing higher parent-adolescent stress were the most likely to engage in subsequent sexual intercourse. Implications for understanding how the association between depressive symptoms and romantic and sexual experiences develops and the course of this association are discussed. (Contains 1 figure and 4 tables.)