The author views Kohut's conceptualization of psychoanalytic empathy and its subsequent development by intersubjectivity theorists as an extension of a larger Romantic epistemological tradition in which the role of imagination in mental life is both central and precise. To illuminate this argument, the author reconsiders Kohut's distinction between the “presence of empathy” and “empathy as a mode of observation.” Next is described the way in which the ambivalence represented by this distinction is resolved through intersubjectivity theory. Finally, the author explores several key aspects of the Romantic imagination as a response to Cartesianism in order to evolve an understanding of empathy as a bilateral procedure mediating self-experience and experience of the other.