Many of our most common and difficult ethical dilemmas involve balancing honesty and benevolence. For example, when we deliver unpleasant news, such as negative feedback or terminal prognoses, we face an implicit tradeoff between being completely honest and being completely kind. Using a variety of research methods, in both the laboratory and the field, I study how individuals navigate this tension. Each chapter in this dissertation addresses the tension between honesty and benevolence at a different level. In Chapters One and Two, I examine how honesty and benevolence influence moral judgment. In Chapter Three, I explore how honesty and benevolence influence interpersonal trust. In Chapter Four, I explore how honesty and benevolence influence psychological well-being. Finally, in Chapter Five, I examine how different stakeholders view tradeoffs between honesty and benevolence in an important domain: healthcare. Across these chapters, I identify three key themes. First, for moral judgment and interpersonal trust, benevolence is often more important than honesty. As a result, those who prioritize benevolence over honesty by telling prosocial lies, lies that are intended to help others, are deemed to be moral and trustworthy. Second, despite philosophers’ assumption that individuals would rarely consent to deception, I demonstrate that individuals frequently want to be deceived. Individuals want others to deceive them when it protects them from harm. This desire manifests itself in systematic circumstances and during individuals’ most fragile moments. Third, honesty and benevolence are associated with interpersonal and intrapersonal tradeoffs. Although benevolence seems to be more central for interpersonal judgments and relationships, honesty seems to be more central for creating personal meaning. Throughout these chapters, I discuss the implications of these findings for the study of ethics, organizational behavior, and interpersonal communication.