Social media and digital technologies are ever present in the surround of current traditionally-aged college students. Although research into understanding these experiences is increasing, there is a need for further research into what may be developmentally different for this generation. Postmodern theorists have posited that as a result of digitization, traditional conceptualizations of selfhood and identity may be changing. The contexts and affordances of these technologies are having an impact on human development and contemporary college students are uniquely situated to experience their effects. This qualitative study aimed to understand how these college students conceptualize their sense of self and identity as a result of digital and social media immersion. In particular, this study explored aspects of digital identity and digitized selfhood to surface important behaviors and developmental processes that are being impacted. Sixteen traditionally-aged college students, primarily in their fourth year of college, participated in a series of interviews and observations to probe this question and were selected as exceptional cases for their heavy usage of social technology. During this process, students were asked about how they conceived of their identity and identities online and how it impacted their overall sense of self. Findings for this study did not reveal fully realized postmodern conceptions of selfhood, such as Kenneth Gergen’s (2009) relational self, but participants did demonstrate understandings of selfhood and identity that hinted at this possibility, including what Robert Kegan (1994) would characterize as fifth order consciousness. Identities were found to be subject to contextual and relational processes that required constant maintenance and reconstruction. Additional findings uncovered college student developmental patterns that reach from being externally defined, and beholden to the views of others, towards internal definition, whereby students made conscious choices about social media use. Implications for practice include the need to educate students on digital reputation and identities, the importance of reflection and goal setting in relation to social media, and the necessity to partner with students as our collective understanding of technology evolves.