In 1904, a leather-bound Hebrew Bible arrived at Lilian Ruth Bentwich's door, accompanied by an original Hebrew poem that embodied both romantic devotion and scholarly dedication. Written by Israel Friedlaender, then Sabato Morais Professor of Bible at the Jewish Theological Seminary, this previously unpublished New Year's gift merged traditional Jewish literary forms with deeply personal sentiment. Drawing upon archival materials, including the original Hebrew manuscript and correspondence, biographical and literary analysis reveals how Friedlaender crafted a work that transcended mere courtship poetry to encompass religious devotion and academic commitment. The poem, composed for the woman he would later marry, exemplifies the complex interweaving of personal relationships, professional scholarship, and Cultural Zionist ideology within early twentieth-century Jewish intellectual circles. Through close textual examination, the document illuminates the sophisticated nature of educated Jewish courtship practices and offers rare insight into the private emotional world of a prominent Jewish scholar, demonstrating how diaspora intellectuals navigated the intersection of romantic, religious, and academic expression.