The construction of the self is a central process in adolescents’ life, and an adequate parent–adolescent relationship is an important factor in promoting this development. In order to better understand this development of self within the family context this study examined the ways in which parent–adolescent boundary dissolution, adolescent true-self behavior and motives for false-self behavior are manifested in adolescents’ self-representations. Differences in adolescents’ self-figure drawings as a function of their true-self behavior, motives for false-self behavior, and their experience of various types of boundary dissolution with their parents in a sample of Israeli early to mid-adolescents (N = 333, Mean age = 14.00, SD = .69) were examined. Drawings were coded using the DAP-SPED coding system as well as a more global approach. The findings indicated positive correlations between psychological control with mother and father, triangulation with the father and the number of deviant indicators in self-drawings. Adolescents who drew detached and bizarre self-drawings showed higher levels of motives for false-self behavior with parents. Adolescents who drew bizarre self-drawings experienced higher levels of triangulation and psychological control with mothers and higher levels of triangulation with fathers. The implications for theory and clinical interventions are discussed.