A simile in an ancient Greek or Roman epic poem uses the simile form “A is like B” to frame a brief tale about something outwardly unrelated to the poem’s main story. The simile structure asserts a kinship between two things that come from different conceptual domains. Similes tell highly concentrated immersive stories, which invite the reader to experience and not simply to observe the described situation. To do justice to epic similes, they should be studied both within the immediate narrative contexts in which they appear and within the many webs of meaning that they create. Some of these are found within a single poem, while others emerge across multiple poems over time. A detailed reading of Apollonius Argonautica 2.121–29, which compares a fight between the Argonauts and the Bebrycians to wolves stealthily attacking a flock of sheep, sets out the common features of shepherding similes, the ways that similes tell their stories, and the style and approach of the book’s argument. Shepherding similes embody several relationships that bring out a range of themes fundamental not simply to all the poems in this book, but to any exploration of the human experience.