The study examined adolescents' emotional separation and detachment from parents, analyzing their relations with connectedness and agency, with some aspects of self-other boundary regulation and with problem behavior. The participants were 331 Italian adolescents, aged from 16 to 19 years (mean age = 17.40, SD = 1.14). Separation and detachment were positively related; they were negatively related to connectedness; detachment was also negatively associated to agency. Emotional separation was negatively predicted by empathic concern, perspective-taking and separate self; emotional detachment was negatively predicted by empathic concern and self-other differentiation. Separation negatively predicted internalizing behavior, and detachment positively predicted internalizing and externalizing behavior. Globally, findings showed that emotional separation and detachment are two distinct dimensions of the parent-adolescent relationship. (Contains 3 tables and 3 figures.)