This article explores the relationship between empathy and psychopathology. It deals with the concept of "understanding" in Jaspers’ General Psychopathology, 100 years after the publication of its first edition. The Jaspersian proposal has the person and his/her experience as its primary object of study, just as in Ortegas’ vital reason. Jaspers’ understanding is not rational but empathetic, based on the co-presence of emotional content and detailed descriptions. Jaspers’ methodology is essentially pluralistic, considering both explanation and understanding, necessary for psychopathology. Despite certain limits, the concept of understanding is the backbone of the psychopathological reasoning, and has proven useful over a century of clinical practice. However, it needs a review covering the recent epistemological and clinical findings. "To be understandable" is a relational property that emerges from a semiotic process. Therefore, an effective psychology should encompass an inter-subjective process, and get away from strict rationalism.