It was of primary interest to examine the affective consequences of conformity to gender stereotypes, and to assess if feelings of social approval and authenticity mediate the relationship between conformity and affect. Therefore, we utilized an Electronic Momentary Assessment methodology to capture University of Maryland students’ engagement in gender stereotypical behavior, and their emotional and social experiences during their daily social interactions. Counter to expectations, we found that regardless of one’s own gender, enacting gender prescriptions enhanced feelings of authenticity and feelings of social approval, and enacting proscriptions reduced feelings of authenticity and feelings of social approval. Enacting prescriptions predicted more positive affect and enacting proscriptions predicted a more negative affective experience. Feelings of authenticity and feelings of social approval independently predicted feelings of more positive affect. Overall, our findings suggest that irrespective of gender, engaging in desirable stereotypes has a number of social, personal, and emotional benefits.