Both common intuition and findings from multiple areas of research suggest that when faced with distressing experiences, it is helpful to understand one’s feelings. However, a large body of research also indicates that people’s attempts to make sense of their feelings often backfire, leading them to ruminate and feel worse. In this article, we describe a program of research that focuses on disentangling these seemingly contradictory sets of findings. The research program we describe proposes that psychological distance from the self plays a key role in determining whether people’s attempts to understand their feelings lead to adaptive or maladaptive self-reflection. It suggests that people’s attempts to understand their feelings often fail because they analyze their feelings from a self-immersed perspective rather than a self-distanced perspective. Empirical evidence from multiple levels of analysis is presented to support this prediction. The basic science and clinical implications of these findings are discussed.