The purpose of this study was to examine the relationship between adolescents' perceptions of their parents' encouragement to lose weight and physical activity habits (i.e., exercise habits and sedentary behaviors) and their own physical health-related fitness (HRF) and psychological well-being. Results of structural equation modeling revealed both similarities and differences between boys and girls. Specifically, parental sedentary behavior and encouragement to lose weight related to girls HRF. Among boys, only encouragement to lose weight related to HRF. When inspecting the relationship between HRF and psychological well-being, HRF related to body satisfaction, but not depressive symptoms, among both boys and girls. Results of this study highlight the complex influence that parental perceptions have during adolescent development.