This article studies the act of suggesting symbolic meanings for Christian divine office in medieval Europe. Twentieth-century anthropology placed great emphasis on the anthropologist as an interpreter of symbolic meanings of ritual, but while using indigenous explanations, it did not address explication as a social practice. The phenomenon of systematic symbolical explanation in medieval Europe, I propose, invites a shift in research questions from “what does ritual signify?” to “who proposes symbolic values for ritual, from which position, to whom, when, and why?” The first part of the article analyzes the ninth-century pioneering work of Amalar of Metz, while the second part turns to the heyday of the allegorical enterprise in the twelfth century, in the work of authors such as Rupert of Deutz and Honorius Augustudinensis. Applied to liturgy, the allegorical practice is shown to function as a sophisticated tool to address diversity and historical change, and as a contemplative means to rejuvenate ritual and afford delight in light of contemporary challenges.