Verbal analogies produced during naturally occurring instructional discourse in mathematics were explored using techniques borrowed from studies of language in use (see Wortham & Rymes, 2003). Close examination of two eighth-grade instructional analogies reveals that the language practices of analogy are instrumental in shaping recipients’ relational re-representation of objects being compared, in particular through markers of indexicality and poetic parallel structure. At the same time, close examination of the communicative interactions reveals that these devices may reduce the burden on recipients’ reasoning to the point that they may appear successful at solving the verbal analogy, but their responses can be explained by facility in verbal interaction rather than in mathematical reasoning. These data provide thereby new insights into the “analogical paradox,” the finding that analogies are commonly successful as vehicles for interactionally producing and displaying understanding of new information in everyday contexts but generally problematic when measured for their effects on reasoning in controlled laboratory settings (Dunbar, 1998). We identify a tension between interactional and cognitive success of everyday communicative analogies, meaning that those that are most likely to be interactionally successful may lead to less cognitive engagement for analogy recipients.