Although ZHU Zu-mou is one of the four most famous poets of ci poetry in the late Qing dynasty, his early life remains vague in many aspects. By studying the newly discovered texts, this paper examines the life of ZHU’s friend DI Yu and gives a brief account of their circle of friends of poem and essay. This is significant for the research of ZHU Zu-mou and his ci poetry. Taking their friendship for decades in the late Qing Dynasty as an example, this paper also discusses the normality and extraordinariness of the promotion of scholar-bureaucrats in turbulent times, as well as the complicated relationship between an individual and his destiny.