This article is about the “encounter of two personalities”, Toegye Yi Hwang and Yulgok Yi I. It focused on the “interaction between these two personalities” rather than academic issues. Toegye and Yulgok met twice in their lifetime. The number of meetings is not proportional to the depth of acquaintance. The year 1558, the year of the historic encounter between Toegye and Yulgok, was also the year of the first encounter between Toegye and Gobong (高峯) Ki Dae-seung (奇大升). From Toegye s point of view, “the year 1558” would be a memorable year. During his life, Toegye has appreciated and honored Yulgok as a scholar of the future generation, and Yulgok has respected Toegye and has honored Toegye’s achievements until he passed away. He considered Toegye as one of the two masters (兩大宗匠) of Confucianism in the East, along with Jeongam (靜庵) Jo Gwang-jo (趙光祖: 1482-11519). Yulgok s comment about Toegye saying that the aspect of Confucian scholar took shape with Toegye , represents Yulgok s opinion about Toegye. With the exception of the differences between their doctrine, Toegye and Yulgok have not much to confront each other. The basic difference between Toegye and Yulgok is a difference in the way they describe the theory. Approaching the school of Toegye and the school of Yulgok only from a conflictual perspective is problematic. When looking at the history of Neo- Confucianism, at the end of Joseon, we can see that dialogue and communication were not ignored. There were trials to make encounter Toegye and Yulgok by some of the future scholars who were willing, and they were partially achieved. It is meaningful to read Toegye s doctrine and Yulgok s doctrine through the topics of time, “dialogue and communication”.