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.