Empathy is often a poorly understood concept. While some feel its value to psychoanalysis cannot be overstated, others feel it has been overemphasized as has the value of properly managing empathic failures that arise during an analysis. This paper will attempt to (1) demonstrate how patients sometimes resist empathy and erect barriers to being understood; (2) illustrate how empathy may sometimes be unachievable due to the difficulties encountered when one tries to empathize with the various aspects of another's experience that are in conflict with one another; and (3) propose that analysts may need to go beyond the common definition of empathy in order to help patients question and discard certain cherished beliefs they hold about themselves.