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This chapter focuses on the heterogeneous pathways (including marital and cohabiting union and parenting histories) through which people navigate their family life courses from adolescence through mid-life, and their implications for union dissolution in middle and later life. The analyses draw on data (retrospective, cross-sectional) from the 2011 and 2017 Canadian General Social Surveys. The study sample includes individuals aged 50 and over (n = 14,547) who were in a union at age 50. Sequence analyses are used to identify the most common family life course trajectories among these individuals from adolescence through midlife (ages 15–50). Logistic regression analyses then address the implications of these trajectories for union dissolution in middle and later life (ages 50+). The results reveal four main family trajectories that characterize the earlier years of the adult life course: married with children, cohabiting with children, single or cohabiting without children, and married without children. These family trajectories, together with their level of complexity, play an important role in relation to both marital and cohabiting union dissolution outcomes in later life.