The purpose of this study was to gain a deeper understanding of the collegiate experiences of second-generation, West Indian college students from Boston. Too often, Black students are treated as a monolith in education research and practice. This study provides new knowledge regarding how second-generation West Indian college students communicate and enact their racial, ethnic, and immigrant identities in their relationships with faculty, staff, peers, and family while in college. The theoretical framework guiding this study was Communication Theory of Identity, which centered the connection between identities and relationships. Through the use of narrative inquiry, seven West-Indian participants from Boston completed a demographic questionnaire and shared their narratives through two, semi-structured, in-person interviews. Through hand coding methods and inductive and deductive analysis of the data, five themes emerged: (a) Proving Cultural Authenticity, (b) Defining a West Indian Identity, (c) Differences Exist, but Race Still Matters, (d) Homophily in Friendships, and (e) Representation Matters: Faculty and Staff Relationships. The findings offer insight of how participants viewed themselves, communicated their identities to others, and whether their relationships affirmed who they viewed themselves to be. Participants encountered disparate messages about their race, ethnicity, and generation status, compelling them to respond depending upon their audience and context. In particular, the shift from and contrast between participants’ Boston neighborhoods to predominantly white campuses across Massachusetts contributed to a difference in how participants perceived themselves. In college, participants confronted the racialized component of their ethnicity and grappled with how they were viewed as Black and West Indian. Friendships provided the optimal space and relationship in which participants most easily navigated their racial, ethnic and immigrant status identities. In contrast to their friendships, participants minimally shared about themselves outside of close relationships with Black faculty or staff. The shifts in the racial composition of participants’ environments, coupled with the types of messages they received in their interactions and relationships, demonstrates the connection between relationships, context, and identities.