Although many scholars and practitioners have assumed that workplace friendships lead to desirable organizational outcomes, a growing body of research suggests important complexities and downsides associated with them. This indicates a need to better understand how and when workplace friendships may lead to harmful outcomes, especially in light of organizational and technological shifts that are changing the way employees connect. Drawing on theories of close relationships, social exchange, and boundary management, we present a theoretical framework highlighting how four defining features of friendship (informality, voluntariness, communal norms, and socioemotional goals) are in tension with four fundamental elements of organizational life (formal roles, involuntary constraints, exchange norms, and instrumental goals). We also highlight how mutual self-disclosure and perceived similarity develop and deepen friendships but also lead to downsides for individuals, groups, and organizations. We articulate how specific features of a focal friendship clique (e.g., closeness, maturity, and status of members) may amplify or buffer negative aspects and how social media affect friendship formation and tensions. Our theoretical framework should inform new theory and research on positive relationships at work and boundary management of professional and personal identities, as well as how changes to work and technology affect workplace relationships.