The purpose of this paper is to describe the timing, density and sequencing of transitions for adolescent and young adult females and males in South Africa into sexual activity, pregnancy, parenting, unions, and school leaving. Analyses draw on detailed life history calendar data from a representative probability sample in 2002 of 4,231 14 to 22 year olds living in Cape Town, South Africa. We use survival analysis techniques to measure transitions into first sex, pregnancy, birth, union and first school leaving for males and females. Data from the 1998 South African Demographic and Health Survey are used to highlight patterns in South Africa overall. Important population group differences exist in the timing of first sex, childbearing and stopping school, and gender differences persist as well for first sex and childbearing. Yet adolescence is not a very dense period of life in terms of large proportions of young people experiencing the five major transitions examined in this study (first sexual intercourse, first episode of stopping school, first pregnancy, first birth and first union). Forty-eight percent of males and 43 percent of females experienced 0 or only 1 transition by age 20. However, the pathways taken through adolescence are characterized by more disorder than order in terms of the variety of combinations and chronological sequences of important social and family formation transitions.