Traditionally, the “Theory of Translation” has privileged approaches to translation that assume a clear correlation between faithfulness to the original text (or freedom) and success (or failure). Such approaches depend upon established notions of what constitutes a “word” or “content.” Thus, they are inherently insufficient, privileging in turn certain systems of signification that are not necessarily reconcilable within certain poetic traditions. This is particularly evident in the case of the classical Sufi poetry of Hafiz, whose historical, socio-political, and cultural context is already complicated by the obscurity of the author himself; the subversive role of Sufism; and the ineffability of ecstasy. A “word” is, in many theories of translation, a sign. Yet if we consider the role of the embodied habitation of signs theorized by Aristotle and expounded upon by Saba Mahmood (2009), we can explore each word of poetry not only as a representation of, but also a manifestation of the concept that is being referenced. Furthermore, the cultural assumptions of both poet and translator make the translation of Sufi metaphors (such as being drunk on wine) especially tricky. These cultural particularities stand in sharp contrast to the intimate universality of love and separation, as embodied in the ghazal form of Sufi poetry. Combined, all these aspects of Sufi poetry create a paradox of meanings, making its translation even more difficult to perform, or even assess. In this paper, I argue that the translation of Hafiz is most faithful when it is “inspired”—whether that be in the more traditionally “faithful” approach of Gertrude Bell, or the more controversial “interpretive” approach of Daniel Ladinsky.