Gender differences in health, socioeconomic status, and social resources persist into advanced old age and result in variations in life trajectories and responses to the challenges of longevity. The implications of these differences are examined in a sample of 150 community-dwelling white men and women. The majority are women, a high proportion of whom are unmarried, living alone, functionally impaired, and have reduced financial resources. Men, in contrast, have fewer decrements, they are more independent, and they exercise more control over their environment. However, their well-being may be undermined by some unanticipated events such as widowhood, caregiving, and relocation. Case examples illustrate how the timing of life course events differs among men and women and results in differences in the problems they face in late-late life.