This paper presents a phenomenological account of empathy inspired by the proposal put forward by Edith Stein in her book On the Problem of Empathy, published originally 1917. By way of explicating Stein’s views, the paper aims to present a characterization of empathy that is in some aspects similar to, but yet essentially different from contemporary simulationist theories of empathy. An attempt is made to show that Stein’s proposal articulates the essential ingredients and steps involved in empathy and that her proposal can be made even more comprehensive and elucidating by stressing the emotional aspect of the empathy process. Empathy, according to such a phenomenological proposal, is to be understood as a perceptual-imaginative feeling towards and with the other person’s experiences made possible by affective bodily schemas and being enhanced by a personal concern for her. To experience empathy does not necessarily or only mean to experience the same type of feeling as the target does; it means feeling alongside the feeling of the target in imagining and explicating a rich understanding of the experiences of the very person one is facing.