This paper uses conversation analysis to describe the sequence in which participants in ordinary conversations are sidetracked from the current topic to engage in the repair of a word and display their orientation to asymmetrical linguistic knowledge between them. The participants frame themselves as being in a more knowledgeable and a less knowledgeable position, and this asymmetry provides an opportunity for learning. The analysis of audio recordings of 12 naturally occurring conversations between first and second language users of English reveals that such side-sequenced vocabulary lessons are initiated using at least three methods: partial questioning repeats, explicitly asking the meaning of the word that was just used, and other-directed word searches. The study captures moments in which participants’ language expert and novice identities temporarily become relevant. It also demonstrates how participants alter their relative epistemic positions with each other and redefine the asymmetrical relationships moment by moment in interaction.