Although a growing body of research recognizes the importance of viewing argumentation as a means of understanding rather than combating others, little is known about how teachers cultivate this practice in classroom conversations when teaching argumentation. This study examines how argument can be taught in classroom discourse with an empathizing stance and generates associated pedagogical constructs. Adopting a microethnographic approach to discourse analysis, this study examines the key instructional events in an argumentative writing unit in two high school English language arts classes. The analysis demonstrates that the empathizing stance is introduced in the relationship between arguers and their warrants and the differences existing between arguers. It also generates four pedagogical constructs related to the teaching of argument with the stance: (1) identifying the connection between arguers’ warrants and backgrounds; (2) transposing oneself into others’ backgrounds; (3) exploring interlocutors’ common and divergent grounds; and (4) situating argument in a broader context. It concludes with a discussion of the affordances of teaching argument with an empathizing stance.