In this paper, we examine Jaspers' ambiguous approach to empathy. We start by situating Jaspers' notion of empathic understanding in the context of contemporary philosophical discussions of empathy. We distinguish a phenomenological approach to interpersonal understanding from two influential accounts of other minds, namely, theory-theory and simulation-theory, and then we contrast Jaspers' notion of empathic understanding with a phenomenological approach. We distinguish two basic kinds of empathy, a prereflective nonconative kind and a more reflective conative kind. Then we argue that Jaspers' philosophical conception of human nature as restless and undefinable autonomy makes him reject any kind of comprehensive attempt to understand other people. We try to make sense of this rejection by discussing the epistemological and ethical nature of his notorious 'theorem of incomprehensibility'. This eventually leads us, by way of conclusion, to sketch a method required for making sense of those experiences that cannot be understood via ordinary empathy. The key notion of this method is called 'second-order empathy'.