Modern educational scholarship has not substantially investigated the learning practice of havruta, paired study and focused conversation around classical Jewish texts. In this article, the author analyzes videotapes and transcripts of real-life havruta interactions and proposes a theory of havruta learning as composed of three pairs of core practices: listening and articulating; wondering and focusing; and supporting and challenging. Through a close analysis of one particular havruta session, the author illustrates and probes the havruta practices and the ways in which they can give rise to generative, textually grounded interpretive discussions of classical Jewish texts. This theory may also be a helpful lens for both studying and elucidating text-based discussions of other kinds of texts in small and large group settings.