The Shulamit exerts her passionate desire for her lover from the very beginning of the Song when she depicts her yearning for him with the words:” ישקני מנשיקות פיהו”. As I read the vicissitudes of love and desire throughout the Song, culminating in the profound expression: ’’ עַזָּ֤ה כַמָּ֨וֶת֙ אַֽהֲבָ֔ה ! I am struck by the gendering of desire and the difference between “love” and “desire” throughout the Song. Having been inflicted by eros, she longs for her lover who is often absent, leaving her unfulfilled. His own attraction and desire for her notwithstanding, she refers to herself as lovesick, suffused with the pain of love in separation rather than in joyful union. In this paper, I consider rabbinic midrashim that ponder the relationship between love and death by conveying the pitfalls of excessive love which leads to jealousy, as well as midrashim for whom this statement in the Song evokes the fear of death experienced at Sinai. In contrast, I underscore Franz Rosenzweig’s philosophical midrash of the Song which elevates the personal experience of lover and beloved as the embodiment of revelation, and as the triumph of love and life over death.