This study examines an 8/9th century CE mufakhara (debate or boasting-match) composed by the renowned adib (belles-lettrist), al-Jahiz, and looks particularly at the text’s complex reception in the 20th century. The mufakhara recounts a fictitious and sexually explicit debate between a proponent of the relative sexual merits of slave girls and boys. First, this paper briefly contextualizes the Jahizian mufakhara in the social and intellectual climate of Iraq’s urban centers of the time, and it sheds light on how the author playfully manipulates authoritative discourses to produce meaning in the text. Next, and most significantly, this paper traces the text’s politically fraught reception in the 20th century, emphasizing how and why western scholars reached wildly different and telling conclusions about the social environment of the time and the author himself. In 1957 the French scholar and Jahiz-specialist Charles Pellat edited the first Arabic edition of the mufakhara with an apologetic introduction, claiming that the text was not appropriate enough to accompany al-Jahiz’s other essays. In subsequent years, the mufakhara entered into the larger Jahizian canon, and drew attention from scholars such as Pellat, Van Gelder, Rosenthal, Hutchins, and AbuKhalil. The reception and publication history of the mufakhara betrays not only the simultaneous impulses towards censorship and eroticization (selections made their English-language debut in Playboy Magazine), but also the tendency to impose culturally specific categories and conceptions of sexuality on a text of a different time, place, and cultural milieu. A close reading of the reception and interpretation of this one mufakhara brings into relief the broader challenges, slippages, and anxieties that characterize textual crossings, here from 8th century urban Iraq to 20th century academic institutions and publishing houses. By juxtaposing a close reading of the text itself with its politicized reception centuries later, this paper offers a mixed methodology that combines philological rigor, discourse analysis, and contributions from gender and sexuality studies.