The exploration of gender identity is an important task during adolescence, and changes in gender attitudes are a crucial aspect of this process. This research draws on psycho-social theoretical perspectives to frame the analyses and attempts to contribute to our understanding of the ways in which adolescents select and apply media in the process of negotiating gender attitudes. Data drawn from the Teen Media Project, a longitudinal study of adolescent media use and its influence on social and health-related outcomes, are utilized. First, a model of adolescent gender attitudes is developed using confirmatory factor analysis in a structural equation modeling format. Attitudes related to dating and relationships are found to be a key dimension of gender attitudes generally. Model form is found to fit very well across black and white, boys and girls. In addition, multi-group tests of measurement invariance reveal significant differences in categorical thresholds between boys and girls. Finally, indicators which load well on the latent variables raise questions related to the relative influence of masculinity versus femininity-related attitudes on overall conceptualizations of gender among adolescents. Next, the model developed above is utilized as the dependent variable in a series of OLS regression models that investigate whether relationally-oriented portrayals of dating and romance in various media (television, films, magazines, and music lyrics) longitudinally predict changes in adolescent gender attitudes in an ecological model that includes parents, peers, clergy, and teachers as competing sources of gendered information. Although peers appear to hold the most sway over gender attitudes, the media are found to rival parents as the second most influential agent of socialization. Among media, music lyrics are particularly influential. In general, media content predicted more egalitarian attitudes among adolescents, especially black boys. Finally, magazines as a source of adolescent gender attitudes is explored using longitudinal Heckman selection models that account for exposure to content based on the selection of particular genres. White girls who read adult fashion magazines in early adolescence and strongly identify with magazine content report much less egalitarian gender attitudes. Descriptive information related to magazine genre readership across race and gender groups is also included.