One of the most beloved passages in the Zhuang-Zi text is a dialogue between Hui Zi and Zhuang Zi at the end of the “Qiu-shui” chapter. While this is one of many vignettes involving Hui Zi and Zhuang Zi in the text, this particular vignette has recently drawn attention in Chinese and comparative philosophy circles. The most basic question concerning these studies is whether or not the passage represents a substantial philosophical dispute, or instead idle chitchat between two friends. This vignette has not only received much attention as of late, but commentators from at least Guo Xiang onward have taken the conversation as substantial rather than merely charming. Of the traditional readings that take the passage as substantial, there are two main strategies for taking Zhuang Zi as “winning” a substantial dispute: (1) One that argues Zhuang Zi is undermining Hui Zi’s position without offering a positive position, and (2) another that argues that Zhuang Zi is undermining Hui Zi’s position by offering a positive position. Guo Xiang’s “official commentary” is paradigmatic of the first “negative” strategy, while Wang Fuzhi’s reading is paradigmatic of the second “positive” strategy. The goal in the present article is to present these two strategies for reading the passage by translating and analyzing Guo’s and Wang’s annotations, thereby showing how the passage might be and has been taken as more than frivolous chitchat.