This paper is concerned with Christopher Isherwood’s portrayal of his guru-disciple relationship with Swami Prabhavananda, situating it in the tradition of discipleship, which dates back to antiquity. It discusses Isherwood’s (auto)biographical works as records of his spiritual journey, influenced by his guru. The main focus of the study is My Guru and His Disciple, a memoir of the author and his spiritual master, which is one of Isherwood’s lesser-known books. The paper attempts to examine the way in which a commemorative portrait of the guru, suggested by the title, is incorporated into an account of Isherwood’s own spiritual development. It discusses the sources of Isherwood’s initial prejudice against religion, as well as his journey towards embracing it. It also analyses the facets of Isherwood and Prabhavananda’s guru-disciple relationship, which went beyond a purely religious arrangement. Moreover, the paper examines the relationship between homosexuality and religion and intellectualism and religion, the role of E. M. Forster as Isherwood’s secular guru, the question of colonial prejudice, as well as the reception of Isherwood’s conversion to Vedanta and his religious works.