Unplanned adolescent pregnancy is one of the challenges that South Africa has been dealing with for years. This challenge is further complicated by the soaring HIV/AIDS infection rates, particularly among young people. The study aimed to explore adolescents’ understanding and meaning of the continuing unplanned pregnancies among adolescents in view of high HIV/AIDS prevalence. Thirteen male and female adolescents aged between 14 years and 25 years made up the participants. Three of them are mothers, four are university students and eight are high school learners. The study was undertaken in a high school, a university, and a clinic in Soweto. Unstructured interviews were used and the topics included adolescents’ knowledge on HIV/AIDS, their thoughts on the continued high levels of unplanned adolescent pregnancies, and their perceptions of the consequences thereof. The participants viewed unplanned adolescent pregnancies as a continuing problem within their communities. Unplanned adolescent pregnancy was described as a product of several factors within and beyond the control of young people. Some of the identified contributory factors are impulsivity, perceived invulnerability, financial dependence, and underdeveloped planning on the part of adolescents. Fertility is highly regarded in certain societies. The participants have a good knowledge of HIV/AIDS, which they receive from several sources such as schools, media, etc. However, HIV/AIDS is not always a deterrent to unprotected sex and the subsequent unplanned pregnancies among adolescents. Most participants do not see the relationship between unplanned pregnancies and HIV/AIDS. Instead, some young people see the prevention of pregnancy as more important than the preservation of life through the prevention of HIV infection. Knowledge about HIV/AIDS does not translate into behaviour change. A significant underestimation of personal risk to HIV/AIDS was observed. The fatality and reality of HIV/AIDS is often ignored and denied.