Current research on college men portrays patterns of maladaptive and antisocial attitudes and behaviors. Studies show correlations between college men’s problematic behavior and their adherence to unexamined gender roles. Educators have few examples of men’s pro-social behavior nor the masculine ideology that accompanies it. This study explored college men’s pro-social behaviors through their engagement in educationally purposeful activities operationally defined in the literature as diversity education. Milem, Chang and Antonio (2005) defined diversity education as meaningful engagement with diversity through coursework or purposeful cross-culture interactions in pursuit of educational outcomes. Using an interpretive qualitative methodology, I addressed two primary research questions: (1) How do college men who have been engaged in some form of diversity education describe their experience, and (2) How do college men who have been engaged in diversity education understand and perform masculinity? Expert nominators identified participants. I conducted in-depth interviews and analyzed the resultant transcripts using open and axial coding procedures. Themes derived reflected men’s socialization of masculinity and their experiences in diversity education. Themes included: (a) the persistence of hegemonic masculine ideology, (b) experiences of gender socialization, and (c) the emergence of resistant and aspirant masculinities. Themes associated with the second question included (d) how these college men found their way into diversity education, (e) the challenges and supports they encountered, and (f) their advice for professionals and educators who seek to design effective diversity education experiences. Findings confirmed other studies that demonstrated the influence of hegemonic masculine ideology on college men (Davis, 2002; Edwards, 2007; Harris, 2006). This study adds to the literature by ascertaining how hegemonic masculine ideology permeates the diversity classroom and workshop, heightening men’s concerns about safety and psychological threat. Implications offer insights for educators who design diversity and social justice education for college students.