In this paper, I unpack (A?mad) F?ris al-Shidy?q’s (1805-87) theory of translation as manifest in two of his major texts: his fictional al-S?q ?al? al-S?q (Leg over Leg) and his travelogue, titled Kashf al-Mukhabba? ?an Fun?n Ur?bba (Revealing the Hidden in the Arts of Europe). Examining al-Shidy?q’s linguistic world, which is for the most part predicated on semantic overlap within endless lists of synonymy, I argue that al-Shidy?q saw “contiguity” rather than strict “equivalence” as driving force of meaning. This suggests the notion that translation and, by implication cultural assimilation, is an impossible undertaking. In this sense, looking at al-Shidy?q’s take on the impossibility of translation helps nuance our common view of translation during the Nah?ah, especially in Egypt, which generally projected assimilation and equivalence as preconditions to a cultural participation in modernity—an argument which Shaden Tageldine profoundly advanced in her Disarming Words. Towards that end, I trace the moments in which al-Shidy?q’s text itself is subversive of the over-determined category of “equivalence.” This subversive energy, I suggest, can be explained historically since al-Shidy?q came to an awareness that there cannot be symmetrical relationships between different cultural, literary, and linguistic systems. Navigating different literary, linguistic, and religious worlds, al-Shidy?q found his poetic (native) and translational (trans-regional/trans-national) selves at jarring conflict. On the one hand, his Qur??n-inspired translations of the Bible into Arabic were criticized and rejected by some Maronite Christians, precisely for their lack of rak?kah (linguistic feebleness) which was arguably, but paradoxically, deemed necessary to draw the reader nearer to a “Christian God.” On the other hand, his classical panegyric qa??dah or ode to a European notable was dismissed for its inclusion of the inaugurational part of nas?b (praise of women). Responsive to European taste, al-Shidy?q re-wrote his panegyric by removing the classical part, thus resulting in what Abdelfatt?? Kili?? refers to as “poetic castration” (ikh?a? al-shi?r). In my analysis, I draw heavily on Kili??’s deconstructive method which questions the notions of correspondence and equivalence among different linguistic and cultural systems.