This article centres on the text of the Great Learning associated with Zhan Ruoshui (1466–1560) and Fang Xianfu (1485–1544), as well as the interpretation of their positions. It explores the competitive reaction to it that rapidly emerged among the Neo-Confucian elites, and the impact of this competition on the highly regarded friends and mentoring relationships in the Neo-Confucian discourse during the formal establishment of Wang Yangming’s (1472–1529) Old Edition of the Great Learning and its explanation. In specific discussions, this article focuses on the exchanges and debates related to the Old Edition of the Great Learning. First, it explores the progress whereby Zhan Ruoshui completely rejected the text of the Old Edition of the Great Learning at first, followed by showing passive acceptance towards it, yet actively involved himself in the dispute over interpretation of the book finally. Second, the paper reconstructs how a short-term mentorstudent relationship was being established between Fang Xianfu and Wang Yangming, after which time the differences in interpretation of Old Edition of the Great Learning gradually became more distinct, leading to a philosophical parting of the ways with irreconcilable differences. Furthermore, we can reflect on the writings of future generations about the mentoring relationship on this basis as well. Indeed, the above discussion is important for us to observe why Neo-Confucian scholars were all competing in seeking to establish a new classic text and independent discourse at the beginning of the sixteenth century when the mainstream ideologies and classical foundation were being questioned. From this perspective, it will also lead us to consider the changes in characteristics of the friends, mentoring relationships, and schools in the Neo-Confucian discourse of that time.