Much of the poetic d?w?n of the Andalusi poet Ibr?h?m ibn Sahl al-Isr?’?l? (1212-1251) is made up of ‘udhr? love poetry that has indirect glimpses of erotic desire (al-ghazal al-?ar??). Ibn Sahl was a Jew who converted to Islam, perhaps under pressure from the ruling Almohads, and the sincerity of his conversion has long been debated. The objects of his poet-persona’s desire are usually young men named M?sà and Mu?ammad, the suggestively Scriptural nature of which has contributed to the speculative discussion about the historical ibn Sahl; however, previous scholarship on this ghazal has generally been characterized by limited readings that interpret it to be lighthearted play that either does or does not contain an answer to the question of whether ibn Sahl’s historical conversion was sincere. This paper offers a close reading of selected pieces from ibn Sahl’s Arabic poetry in light of the one surviving Hebrew poem that he likely authored (a baqqaša, or liturgical petition, that includes the poet’s name in acrostic form), in order to reexamine their usage of particular constellations of religious references and how they are mapped onto the conventions of ghazal poetry. Paying close attention to religious allegory and intertextuality in ibn Sahl’s poetry allows this paper to resituate the discussion about the sincerity of conversion in general as conveyed through literary texts. In his ghazal ‘udhr?, ibn Sahl often alludes to Israelite prophets, recasting them through Qur'?nic narrative as objects of aesthetic and romantic desire. In this way, Ibn Sahl’s poetry reverses the convention of using religious language to describe feelings toward the beloved in classical Arabic love poetry, the effect of which is a unique use of this genre that may covertly convey a socially problematic ambivalence toward the Jewish religion. In both the Hebrew and Arabic poetry, the tone is melancholic and lachrymose, expressing a conflicted desire that provokes guilt and yearning simultaneously. Rather than answering a ‘yes or no’ question about ibn Sahl’s biographical conversion, the tone and genres that ibn Sahl employs appears to offer qualitative insight into the often ambivalent and dialectical experience of religious conversion.