Gray divorces, or divorces at and over the age of 50, are increasing in the United States. This article explores this population's interest in remarrying after a divorce by sex within the context of a prospective, role exit theoretical framework. In‐depth, qualitative interviews with 40 women and 39 men who have experienced a gray divorce were analyzed using grounded theory methodology. There were significant gender differences with respect to receptivity to remarriage among those who had undergone a gray divorce. More specifically, the most common theme expressed by women involved firmly rejecting remarriage as a part of their futures. The remaining themes articulated by women were conditional pro‐remarriage views and then even less commonly, unconditional pro‐remarriage views. In contrast, the most common theme among men was that they remained very open to remarriage, either unconditionally or under specified conditions; only a small number rejected the prospect entirely. These findings highlight the differences in the remarriage decision from both the female and male perspectives for this population.