This chapter explores the conditions under which reciprocal learning occurred between two Canadian and Chinese primary school teachers at a Canadian school participating in the Canada–China Sister School Network. Using narrative inquiry as our guiding methodology, we employed Xu and Connelly’s (Frontiers of Education in China, 12(2), 135–150, 2017) Reciprocal Learning as Collaborative Partnership framework to examine the pair’s co-planning and co-teaching experiences. As sources of insight into the teachers’ collaboration we collected field texts, and conducted in-class observations and follow-up communications. The chapter reveals that despite the Sister School Network’s aim to foster reciprocal learning between teachers from different educational systems, such an outcome cannot be taken for granted simply because teachers happen to be interacting with each other. Teaching practices in Canada and China are rooted in distinct educational beliefs and pedagogical approaches, and reflect important differences between the generalist and specialist teaching models practiced in Canadian and Chinese education systems, respectively. This study highlights the importance of understanding these differences to better facilitate reciprocal learning between teachers from diverse cultural contexts. We highlight the importance of building reciprocal and collaborative relationships as a hopeful basis for exploring different educational practices in diverse cultural contexts and to encourage harmonious cross-cultural relations between East and West.