How do men develop sexist attitudes, gender role conflict, and subjective masculinity stress? These questions have been given little attention in the literature. Given the strong relationships between these variables and men’s poorer mental health, it is essential to understand their antecedents. This study seeks to elucidate the manner in which perceptions of fathers may influence sons’ gender attitudes and experiences. Using a sample of 170 undergraduate men, the authors proposed a model in which perceived paternal modeling of masculine norms and perceived paternal sexist communication mediate the relationship between perceived paternal authoritarianism and our three outcome variables: sons’ sexism, gender role conflict, and subjective masculinity stress. They also hypothesized that the father–son relationship quality would moderate these mediating relations. Results were consistent with a model in which both perceived paternal modeling of masculine norms and perceived paternal sexist communication mediated the relationship between perceived paternal authoritarianism and sons’ sexism. However, only the indirect effects from perceived paternal authoritarianism to gender role conflict and subjective masculinity stress through perceived paternal sexist communication were significant. Two significant moderated mediation findings underscore the complexities of the father–son relationship—the quality of this relationship was a risk factor for sons’ sexism but a protective factor for sons’ subjective masculinity stress. These results suggest an intricate portrait of the perceived influence of fathers on their sons’ gender development and stress. Practical implications for counseling psychologists as they relate to both counseling and prevention are discussed.