The study examined the association among mothers' parenting stress, adolescents' emotional separation and self-orientation toward connectedness. Participants were 194 Italian adolescents, aged from 15 to 19 years (mean age = 17.39, SD = 1.18), and their mothers, aged from 33 to 64 years (mean age = 44.35, SD = 5.40). General findings showed that adolescents' emotional separation may not necessarily be associated with their mothers' parenting stress, but both of these variables may be related to adolescents' personal characteristics, which may contribute to define parent-child relationship. Particularly, adolescents' orientation towards a connected self was associated negatively with emotional separation and parenting stress. These findings indicate potential pathways to mitigate the stress in facing the normative challenges of adolescence.