This paper explores historical contributions to the questions of self, experience and its boundaries through the examination of psychological conceptions of sympathy and empathy at the outset of the twentieth century. I will chart the beginnings of a discourse on empathy (Einfühlung) in German psychological aesthetics in the latter part of the nineteenth century and then discuss the ways empathy became a means for the understanding and identification with others in psychological circles. Finally, I discuss the ways various conceptions of empathy were incorporated into the clinical psychiatric context by a selected group of psychiatrists, most of whom were inclined towards phenomenological approaches to patient experience.