One year before his death, the prominent Egyptian intellectual Lewis ‘Awad (1915-1990) published his memoir entitled Awraq al-‘Umr. In a shocking confession style, ‘Awad gives a detailed account of his visits to the brothel in downtown Cairo while he was a college student in 1930s. Born in al-Minya province and educated in Cairo, Cambridge and Princeton universities, ‘Awad was the first intellectual of his stature to speak openly about his experiences in the brothel as what downtown Cairo offered him and his generation of provincial young men who came to the capital city seeking modern education in the newly restructured Ahliyya University, Cairo University now. Taking Lewis Awad’s autobiography as a starting point, this paper studies downtown Cairo as a site for both moral and nationalist clashes in colonial and post-colonial periods. Based on memoirs, archival research, and the contemporary press, this study explores the underworld of downtown Cairo brothels through the eyes of students and provincial young men in the last century. It discusses how having downtown Cairo as a destination for entertainment and leisure time contributed to a subculture where particular sex-workers won the nickname sadiqat al-talaba, or the friend of students. The nickname meant attracting young inexperienced men to receive sexual services in safe inexpensive brothel. Meanwhile, the concentration of licensed brothels in downtown adjacent to foreign-owned businesses and hangouts turned the area into a site of clashes between young nationalists and foreign soldiers in the colonial period. Yet, when the state outlawed sex-work altogether, the Downtown Cairo area continued to host illegal sex-work in the memories of ‘Awad’s generation and according to state security reports.