In this chapter, the researchers used an ethnographic stance to demonstrate how conversation evolved within a social media platform. They investigated the online discussions and face-to-face dialogues between teacher educators and pre-service teachers. They compared the participants’ reciprocal conversations within this case study to analyze patterns in the language used in each forum in order to identify the affordances and constraints of perceived understanding. Through this discourse analysis the authors sought to identify indicators of each participant’s metacognitive development while engaging in an online book discussion through a social media platform. Data analysis indicated that there was metacognitive growth when comparing the initial reciprocal conversations with the final conversations.