Humans are social animals. We spend roughly 80 % of our time around others (Cacioppo, Fowler, & Christakis, 2009). For better or worse, relationships with others greatly impact us. In fact, positive relationships are vital to our well-being (Baumeister & Leary, 1995). However, some people have personality traits that impede their ability to participate in and benefit from stable, positive, and satisfying relationships. Life is difficult for such people. Being disconnected from others creates psychopathology by thwarting a basic need for close relationships. Perfectionism is a personality trait robustly associated with both social problems and psychopathology. The social disconnection model (SDM; Hewitt, Flett, Sherry, & Caelian, 2006) is an integrative theoretical framework clarifying how perfectionism generates psychopathology through negative social behaviors (e.g., conflictual interactions), cognitions (e.g., seeing others as disappointed), and outcomes (e.g., romantic breakups). In the present chapter, our goal is to articulate an expanded SDM that addresses limitations of the original formulation of this model. We also present two case studies illustrating how the expanded SDM is applicable to two well-known perfectionists: Sylvia Plath and Steve Jobs. But first, we define perfectionism, outline the original SDM, and discuss research supporting it.