This essay explores the journey college men face as they negotiate the formation and development of their digital and masculine identities from first year to senior year. Several objectives guide this article: (1) to provide insight into how and why the landscape of identity development has shifted for men; (2) to offer recommendations for practitioners who are charged with supporting these men in their development; and (3) to share data highlights from a qualitative study that was conducted to explore how masculine and digital identities were articulated by first-year men and senior-year men. The research study focused on examining how social media use influenced the gender identity and gendered performance of first-year and senior college men on a predominately White institution (PWI), residential campus in the Midwestern United States. By the time men become seniors, they often have shifted to become more thoughtful and reflective in their online presence, choosing to align their digital values with their in-person values while putting on the best forward-facing image to attract future employers and partners. Challenging men to unmask themselves in physical spaces and on social media--and supporting them to understand that both spaces carry equal weight in the digital age--remain critical steps in dismantling hegemonic cultures and perceptions of hypermasculinity that create challenges for men.