Meshullam da Piera was an important Hebrew poet who lived and wrote in Gerona, Spain in the post-Andalusian climate of the thirteenth century. One of the major issues that has attracted the attention of scholars who deal with Da Piera is his frequent tendency to favor an enigmatic, vague style in his poems, whose incoherent flow and odd word choice are explained in different ways. This article presents an English translation as well as two separate readings of one of his ambiguous poems in a joint attempt to decipher and applaud the poet’s mastery and ingenuity. The poem, “Li rinenah tsipor” (“A bird has sung to me of love”) is a long, complicated poem of sixty-five lines. It is loaded with characters including the poet himself, a wondrous dove, the poet’s fickle friends and rivals, an envisaged damsel and a lord named?Amram, and it is organized around a description of the poet’s obscure dream, which is followed by a rebuke of his allegedly loose mores. Our readings depart from one another mainly in terms of who expresses the rebuke: the female figure who appears in the dream or the poet’s friends. The fact that the poem itself does not provide a clear answer to this fundamental ambiguity is what prompted us to present our two interpretations that develop in different directions. The first reading, by Oettinger, claims that the poem incorporates the atmosphere and the ideas of the poet’s circle of mystics in Gerona and suggests an inner, silent reflection governed by a divine vision. The second reading, by Kfir, interprets the poem as a complex psychological process of a lonely old poet who is anxious about his place within society and traces the process by which his psyche constantly struggles, sways, and strives for reconciliation. We believe that our different readings are not simply two subjective perspectives but rather are generated by the unique features of Da Piera’s poetry, which themselves invite more than one interpretation.