Masculine roles in the media are constantly changing and those evolving roles had not been observed in a decade. This research was conducted to investigate levels of masculinity in the print medium among a variety of target audiences. Its goal was to decipher how portrayals of masculinity changed based on the magazine's target audience, and several coding factors were used to determine that information. To prepare, a review of advertising and gender, psychological and communication theories, the changing nature of masculinity, feminine impact, target audience participation and an array of relevant past research was conducted. Over the course of this content analysis, 315 advertisements from nine magazines over three years were examined to distinguish changes in masculine roles based on the magazine's target audience. While few significant correlations were found, the results pertaining to raw data have proved to be a significant addition to the body of knowledge on the portrayal of male roles, especially in comparison to past research's results that were displayed in raw data without significance testing. Results show some findings consistent with past research, and some new developments as well. Overall, it was found that masculine portrayals are inconsistent among target audiences. Therefore, theoretically men and women are creating differing constructs of the masculine man, which could result in male-to-female relational conflict.