The study examined the applicability of the observational technique developed by Allen and colleagues (Allen, Hauser, Bell, & O’Connor, 1994; Allen, Hauser, et al., 2003) to investigate the issues of autonomy and relatedness in parent-adolescent relationship in the Italian context. Thirty-five mother-adolescent dyads participated to a task in which they discussed a family issue about which they disagree. Adolescents were also administered a self-report measure assessing their relationship with mothers. Mothers reported significantly higher levels of promoting and inhibiting autonomy, and promoting relatedness behaviors than their children. Results also suggested a partial behavioral reciprocity within the dyads, regarding promoting and inhibiting relatedness, and inhibiting autonomy. Finally, mothers’ inhibiting autonomy behaviors positively correlated to teens’ perception of their relationship as conflicting; adolescents’ inhibiting and promoting autonomy and inhibiting relatedness behaviors positively correlated to open confrontation, rejection and coolness, while promoting relatedness behaviors negatively correlated to open confrontation, rejection and coolness. The results suggest that, for Italian mothers, behaviors linked to autonomy seem to be associated with being involved in a more negative relationship with their children, even if not characterized by open hostility, while for Italian adolescents, behaviors linked to autonomy seem to be associated with threatening the closeness of the relationship. Globally, the findings suggest that the application of this observational procedure may help our understanding of youth autonomy and relatedness development in Italy, but they leave unanswered questions regarding its appropriate adaptation and the role played by cultural differences.