Studies show that the economic benefits of marriage carry over into old age and that widowhood and divorce have detrimental economic consequences, especially for women. This study asks how affluence and poverty are affected by the timing of widowhood and divorce and tests whether they operate in symmetry. The study draws on Israel’s annual Social Survey from multiple years (2013–2017), conducted by Israel’s Central Bureau of Statistics. The sample is limited to older individuals, aged 55+ (n = 4824 men, 5643 women). The findings show that married people are less likely to be poor than unmarried people, but they are not always more likely to be affluent. Widowed men and women, and divorced men are more likely to achieve affluence than continuously married couples. The explanation may be that, in the Israeli context, the widowed tend to inherit benefits accumulated by their late spouse, whereas the divorced tend to divide resources when the marriage dissolves. Women incur higher and longer-term penalties for their change in marital status than do men, so that previously married women tend to have higher rates of poverty and lower rates of affluence than previously married men. The findings show that affluence and poverty do not operate in symmetry and that affluence does not simply mirror poverty, especially among men. For example, early widowed and late divorced men have higher odds of both poverty and affluence than married men. These findings demonstrate that poverty and affluence operate differently and examining both leads to new insights.