Young persons who identify as male experience a different culture than the one experienced by their counterparts decades – or even just years – ago. Amidst a changing job market, a media culture reliant upon unflattering masculine tropes, and a contentious cultural landscape wherein men treat women with open disdain in media, politics, and the business world, these young men often find themselves in uncharted waters without a clear route forward. (Uncharted waters for men, that is; women have experienced destructively choppy waters for generations while men enjoyed unearned privilege. For a discussion, see McIntosh, 2000.) That being said, there is great diversity in the gender role socialization that each American male experiences, so each young man has varying degrees of enculturation and similarly unique responses. From the culture-based rules about how men should interact with women or with other men, to even more foundational questions about what it means to be a man in the first place, there is great debate about a clear model for modern masculinity. While some young male-identified students are thriving despite changes in both culture and experience (Harris & Barone, 2011), healthy norms for Western masculinity seem far out of reach for the university culture writ large. Intentional and comprehensive interventions – like those provided by an engaged experience with higher education (Delbanco, 2012; Felten, Gardner, Schroeder, Lambert, & Barefoot, 2016) – may prove some of the only opportunities that lead to greater understanding.