Male circumcision and marriage are significant cultural practices that mark a critical stage in a person’s life in many African societies. Many rites of passage that exist, circumcision and marriage are intertwined. Marriage and circumcision like other cultural themes have attracted wide scholarship of diverse depths. Such studies have underlined, among others, the nature, forms, types and even the place of the two initiation rites in society. What, however, has not received adequate attention are the (re)negotiations and contestations between morality and masculinities in the context of male circumcision and marriage. Based on this understanding, and drawing on the findings of a qualitative study conducted in Kisii, and Homa Bay counties in South-Western Kenya, the researchers in this paper argue that circumcision and initiation determine ones’s masculinity, which as well acts as a gateway to marriage and social wellbeing. Combined, the two cultural practices can be presented as central morality and cultural notions that inform, underpin, and serve as the dominant paradigms that direct the lives and activities of African people from birth to death. The study suggests that despite its significance over decades, the practice of circumcision has changed over time in relation to the importance people attach to it, how it is practiced, and the attention it attracts from the society. The study recommends the need for a critical interrogation of morality in relation to what fits individuals and the contemporary world as they practice the rites of passage, while at the same time maintaining what is morally acceptable in the society.