This ethnographic research, conducted among young people (aged 18-35) in urban Addis Ababa, Ethiopia, focuses on young people’s encounters with contemporary reproductive and sexual health technologies, in particular Postpill (an emergency contraceptive pill) and Cupid (a branded generic of Viagra), to shed light on their sexual health concerns, aspirations and the kinds of (wo)manhood they aspire to. Although Postpill is recommended for use only in emergencies, and Cupid only when diagnosed with erectile dysfunction, both are commonly used outside of these biomedical contexts by young men and women in Addis Ababa. The popularity of these products seems to emerge against a background of changing gender relations and sexual expectations. Young women are engaging more in premarital sex, and young men feel pressure to perform. Cupid and Postpill offer them ways to resolve these tensions in their lives, but at the same time new problems arise. Some young men appear to be dependent on Cupid for their sexual conduct, while young women still need to live a double life, where they cannot openly admit to being sexually active.