“Love” is a term too often deployed in an insufficiently examined way. As such, it turns out to be remarkably vague—in fact, confused. Bringing the harder-edged psychoanalytic notion of transference love to bear upon the relatively fuzzy notion of “true love” can help to clarify some of this confusion, placing pressure upon the essential nature of what we call “love.” In particular, the concept of transference love highlights some of the complexities surrounding the ideas of genuineness (rather than, say, performance or fakeness), constancy or stability (rather than infidelity or promiscuity), and uniqueness (rather than repetition or substitutability). Both Shakespeare (in Anthony and Cleopatra) and Freud (in his gradual working out of the idea of transference) engage in a keen interrogation of what love is, how it may be inflected through repetition, what forms its ambivalence takes, and whether it can be said to exist in the absence of (re)enactment. For Freud, in the end, what we call “love” is haunted by transference love; conversely, transference love is the very condition of what we call true love. This essay suggests that Anthony and Cleopatra undoes the apparent opposition between Freud’s echte Liebe and Ersatzliebe. Both Shakespeare’s play and Freud’s comprehension of transference offer a paradoxical perspective that transcends the divide between genuineness and (mere) make-believe, between emotion and (mere) performance, between faithfulness and fungibility, between psychic fixity and mobility, and between chance (or haphazardness) and choice (or careful arrangement).