In this paper, through the theoretical lens of life-course research and reproduction theory, we employ 15 years of longitudinal data from the British Columbia, Canada "Paths on Life's Way" project to examine the extent to which educational and career pathways of this cohort of 1988 high school graduates are gendered, individualized, prolonged, diversified; to determine marriage and parenthood patterns in relation to educational and occupational participation and outcomes across time; and to assess the extent to which social class still matters. We employ a transition probabilities analysis to follow the journeys of over 730 individuals from high school through the post-secondary system and work by identifying a sequence of significant stages. We then correlate these transition rates with relevant factors that influenced respondents' lives. We demonstrate quantitatively that although the life courses of young women and men are experienced differently, there is an overall regularity in outcomes. Their "choices" at key transition points are to large extent shaped by external structures and social class and gender differences are evident. (Contains 9 tables, 4 figures and 3 notes.)