The issue of how to contextualize personality psychology constructively has been a longstanding dilemma. This special issue brings together personality, social, self, clinical, and cultural psychologists who have attempted to contextualize the self, personality, attachment, and cultural constructs in an integrative fashion, with a focus on broader situations, such as social roles. In this introductory essay, I describe the potential advantages of integrating traditional concepts in personality psychology with social roles and provide an overview of the contributions made to the special issue.