Individuals’ social and professional arenas entangle so easily today with the rise of social networking sites (SNS). Drawing upon the boundary and social exchange theories, this study investigates whether supervisor–subordinate interactions in cyberspace will spill over to the workplace. A two-dimensional typology of hotel employees is delineated on the basis of their SNS interaction behaviors. The moderating effect of individual type is also investigated. The results indicate that supervisor–subordinate SNS interactions could transition to favorable leader–member exchanges in the workplace that, in turn, promote employees’ organizational citizenship behaviors. In addition, the impact of SNS interaction on leader–member exchange is stronger for employees with proactive personalities and self-disclosure tendencies. This study fills the void of inadequate empirical literature on hierarchical friendship in cyberspace and advances research on the moderating effect of employee personality. Managerial implications are also discussed.