Gender role conflict theory has made a significant contribution to the area of men’s health (O’Neil 2008). However, despite its popularity, numerous criticisms have been directed against the GRCS – both theoretical and psychometric. For example, items have been critiqued for not directly measuring conflict “as it is generally understood (i.e., the result of two competing response tendencies)” (Betz & Fitzgerald. Annual Review of Psychology, 4(1), 360, 1993). Recently, an attempt was made to develop an adolescent version of the GRCS (Blazina et al. Psychology of Men & Masculinity, 6(1), 39–45, 2005). None of the psychometric concerns that had been raised about this scale were addressed and only nominal changes were made to item content (e.g., “When I am sexually involved with others, I do not express my strong feelings” was modified to “When I am personally involved with others, I do not express my strong feelings”). A vital omission was that, in the development of this scale, adolescents did not inform item generation, and no contact was made with adolescents to see if they considered factors, traditionally used with men, to possess personal relevance (i.e., there is no reference to face or content validity). A psychometrically sound measure which targets adolescent boys should be “grounded in and relevant to [their] experiences” (Chu et al. Men and Masculinities, 8(1), 99, 2005) as there may be factors used in adult scales that are not salient to younger individuals. Conversely, there may be latent factors left unexplored or unrealized when researchers do not involve adolescents in the formulation of scale items. This chapter outlines critiques of gender role conflict theory and of the psychometric properties of the adult and adolescent versions of the GRCS. Advancements in psychometric theory and in masculinity research have occurred since the GRCS was created in 1986. Thus, the chapter argues that this measure needs to be updated. Using data obtained from focus groups and personal interviews of adolescent males residing in the Republic of Ireland, the authors contend that modifications to GRC, as it pertains to adolescents, are required. Such modifications will ensure that resultant measures are culturally nuanced and cohort specific. It is anticipated that this chapter will make an important advance in social scientists’ understanding of gender role conflict theory as adolescents experience it.