It is commonly believed that reminiscence is adaptive in late life, but the sparse research on this topic has produced mixed results. This article suggests that one reason for inconsistent findings is the failure to consider social contexts. Interview data from three subgroups of residents of two retirement communities (widowed men, widowed women, and single women; N = 43) revealed sharp differences in the relationship between key aspects of reminiscence and two measures of adaptation (life satisfaction and self-esteem). For widowed men, elaboration of memories, life reviewing, and high importance of others were associated with positive adaptation, but the reverse was true for widowed women. Single women were intermediate, but those who had high peer contact were most similar to the adaptive pattern of the widowed women. Widowed men with high peer contact were most different from the widowed women. Several explanations for these differences are considered, including gender-role differences, life-course continuity, and the social composition of the retirement communities.