The purpose of this qualitative, in-depth interview, study was to understand the experiences of heterosexual male Resident Assistants (RAs) from a gendered perspective taking into account their leadership position and identity development. The significance of this particular topic is underrepresented in literature. Heterosexual male RAs have not been subjects for most masculinity studies and little research actually has considered the identities of heterosexual men as gendered individuals. Therefore, heterosexual males in a compassionate leadership position may suffer from being ignored and dismissed as not having developmental situations imposed upon them directly by this position. The results of this study include an understanding of how heterosexual male RAs identify their masculinities and the pressures they feel from societal gender norms. Implications include suggestions for how to advocate for male RAs and improve training to promote greater success for heterosexual men.