By 2020, brands will invest half of their marketing budget on Internet advertising. The Internet has effective potential in advertising, and it can mold stereotypical roles for future generations of consumers. Social norms and beliefs towards respect and gender equality can be reinforced through digital advertising. This study compares empirical evidence of how women are portrayed in digital advertising on Facebook from Mexico and Chile. Samples were compiled by selecting forty fan pages with the most followers-20 from Mexico and 20 from Chile. 1600 posts were examined by quantitative content analysis method. Results show that Mexican posts use 10.2% more sexist stereotypes than Chilean posts. In a traditional role's context, advertising emphasizes behaviors along gender stereotypes, where women are not perceived equal to men. "I love shoes" (97.5%), a Mexican company with the second highest number of followers and "Forever 21," an American juvenile clothing brand (85%) in Chile, are the brands that portray women in mostly traditional roles. These data reinforce the theory that femaleaudience brands support sexist values in advertising. Both countries show women engaged in activities outside the home, but not professionally or as an authority figure. Summary, in many ways, evidence suggests a paradoxical approach to portrayals of women in Mexican and Chilean Facebook fan page advertising.