Self-compassion is a positive psychological construct associated with heightened well-being, but the construct is largely measured via self-report. In a study of divorcing adults (N = 120), we sought to replicate and extend prior research on the association between self-rated and observed self-compassion, the linguistic cues associated with self-rated and observed self-compassion, and the predictive utility of observed self-compassion. Untrained observers rated participants’ stream-of-consciousness recordings about their marriage and separation experience. We found adequate consensus among raters of observed self-compassion and a significant, positive association between self-rated and observed self-compassion. Greater self- and observer-rated self-compassion were associated with less distress at baseline; however, only observed self-compassion was associated with less distress at the final study assessment. Discussion centers on the cues observers use to perceive self-compassion in others and the extent to which behavioral manifestations of affect may shape such ratings.