This chapter shows that against the background of intentional ignorance of Hebrew in traditional society, the study of Hebrew and its grammar became a central component of the process of becoming a Maskil [an enlightened Jewish person]. Because those who studied the Bible and Hebrew grammar were often suspected of heresy and forced to study in secret, the study of Hebrew, and even more so—the writing and publication in this language, became the ticket of entry into the male Maskilic community. Borrowing the notion of “rite of passage” from anthropology, the chapter analyzes the process of becoming a Maskil as an informal rite of initiation into the Maskilic community. It highlights the role of literacy events in this rite, and shows that it served to constitute not only the young “initiates’” Maskilic identity, but also their male gender identity. The study of Hebrew grammar was not only an initiation into Haskalah but also a shift from the mother tongue (Yiddish) to the father tongue (Hebrew) and from the feminine sphere to the masculine one. The writing and publication of a Hebrew text symbolized both mastery of the “masculine” Hebrew language and entry into the circles of modern, enlightened, Jewish Men.