Research based on the Eccles model of parent socialization demonstrated that parents are an important source of value and ability information for their children. Little is known, however, about the bidirectional effects between students’ perceptions of their parents’ beliefs and behaviors and the students’ own domain-specific values. This study analyzed how students’ perceptions of parents’ beliefs and behaviors and students’ mathematics values and mathematics-related career plans affect each other bidirectionally, and analyzed the role of students’ gender as a moderator of these relations. Data from 475 students in 11th and 12th grade (girls: 50.3%; 31 classrooms; 12 schools), who participated in 2 waves of the study, were analyzed. Results of longitudinal structural equation models demonstrated that students’ perceptions of their parents’ mathematics value beliefs at Time 1 affected the students’ own mathematics utility value at Time 2. Bidirectional effects were not shown in the full sample but were identified for boys. The paths within the tested model varied for boys and girls. For example, boys’, not girls’, mathematics intrinsic value predicted their reported conversations with their fathers about future occupational plans. Boys’, not girls’, perceived parents’ mathematics value predicted the mathematics utility value. Findings are discussed in relation to their implications for parents and teachers, as well as in relation to gendered motivational processes.