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Weight concerns are common among adolescents and are associated with a range of negative psychological and physical health outcomes. Self-esteem is one correlate of weight concerns, yet prospective research has not yet documented the direction of this association over the course of adolescence or whether this association differs by gender. This study sought to clarify the role of self-esteem in the development of adolescents’ weight concerns and investigate the potentially protective role of father and mother responsiveness, another documented correlate of weight concerns. Participants were 392 predominately Caucasian/European American adolescents, ages 11–18, and their parents. Time-lagged mixed-effects models revealed bidirectional associations between self-esteem and weight concerns at the within-individual level over the course of adolescence. Results also confirmed the moderating roles of youth gender and father responsiveness in the prospective link between self-esteem and weight concerns such that father responsiveness buffered the effects of low self-esteem on weight concerns for girls but not boys. Only gender moderated the prospective link between weight concerns and self-esteem: On occasions when youth reported higher self-esteem than usual (compared to their own cross-time average), they reported fewer weight concerns the next year, but this effect was slightly larger for boys. Findings suggest that self-esteem and weight concerns are reciprocally related in adolescence and highlight the importance of examining interactions between family processes and individual characteristics to predict adolescent psychological adjustment.