Kisses have an uneasy relationship with time. They are ever desired, withheld, stolen, and multiplied because they create more longing than they satiate. The kiss is both sensual and spiritual, direct and oblique, unifying and dividing – it is the embodiment of the erotic paradox. From its origins in the Song of Songs and Catullus, to the Basia of Secundus and the baci mordaci of Marino, the tradition of kiss-poetry conveys the pleasurable frustration of talking about love instead of making it: the necessity of speech acts in bringing about the physical act of kissing, and the impossibility of simultaneity between the two. Monteverdi’s engagement with the poetic conceit of kisses – mouths uttering delights by actions, words, and song – dates to his introduction to the poetry of Torquato Tasso (1544–95) during his final years in Cremona. This chapter traces the history of kiss poetry to focus on Monteverdi's earliest interactions with kiss poetry, the madrigals from his Second Book of 1590.