The capacity to share and understand another’s state of mind or the ability to put oneself into another’s shoes or, in some way, experience the outlook or emotions of another being within oneself has been referred to as empathy. It is a presumed ability to burrow into another person’s structures of consciousness and experience oneself as another. Hence it involves the capacity of one to understand or feel what another is experiencing from within their frame of reference. This paper investigates the im/possibility of empathy. The question of the im/possibility of empathy finds expression in the question of the possibility of a subject’s access into the subjective conscious experiences of another. The paper appraises various positions accruing from the basic Husserlian/Steinian views. It also highlights the optimists’ belief that empathy puts us in touch with others in a way that generates a compassionate concern that forms the foundation of morality and the pessimists’ view that empathy merely blurs the distinction between oneself and others, yielding self-interested motivation or at least precluding genuine altruism. This paper suggests that the problem of the im/possibility of empathy would persist in so far as the definition of empathy involves ‘feeling with’ rather than ‘feeling for.’ As Diana Meyers puts it, “the metaphor of putting oneself in the other’s shoes is misleading, for it is a mistake to assume that the other feels the same way as one would oneself feel in the same circumstances.” Thus, it is either that empathy is unreal or what is considered as empathy requires a redefinition.