The objective of the study was to investigate how self-enhancing evaluations, obtained via positive social comparisons and reflected appraisals, were related to mental health in a later life transition. The sample consisted of 266 women who were interviewed once before and 3 times after the experience of community relocation. Results extended prior findings suggesting the dynamic impact of self-enhancing evaluative processes on psychological well-being and depressive symptoms. Additional analyses showed evidence for reverse causality, that is, that mental health also influenced self-evaluative processes. This study underscores the significance of holding a positive view of self vis-à-vis others in negotiating life challenges as well as the reciprocal influence of well-being on social self-evaluative processes.