Subtle occurrences of discrimination, insults, and slights against gender can impact woman of all ages, although little research has been done on the mental health impacts of these events on adolescents or middle-aged women. Additionally, a person’s own views on sex roles and sexism may impact how these events affect them. The following study examined the relationship between mothers and daughters on variables related to ambivalent sexism, gender-based microaggressions, and anxiety and depression. One hundred two mothers and their adolescent daughters completed various online surveys through the use of a Qualtrics panel. The sample was fairly representative, with respondents varying in social class, age, religious preference, and geographical location. Mother and daughter participants separately completed various online measures related to microaggressions, sexism, and mental health. Results indicated that mothers and daughters reports of mental health outcomes, experiences of microaggressions, and ambivalent sexism were very correlated. Additionally, for both mothers and daughters, there was a positive correlation between experiences of gender-based microaggressions and increased symptoms of anxiety and depression. A moderation analysis was done to see if a women’s level of benevolent sexism acted as a moderator to the relationship between experiences of microaggressions and mental health. Although no significant interactions were found, the results did approach significance for the dependent variable of mother’s depression. This study highlights the occurrence and impact of gender-based microaggressions on two under-researched populations, and also begins to explore how views about gender roles may interact with mental health.