In this article, we investigated the extent and nature of informant discrepancies on parent- and adolescent self-report versions of a checklist measuring youth exposure to life stressors. Specifically, we examined (a) mean-level differences, relative consistency, and consensus for family-level and youth-specific stressors and (b) the utility of parent–youth discrepancies in accounting for variance in youth temperament and psychopathology. Participants were 106 parent–child dyads (47 male, 59 female; 90.6% mothers) aged 13 to 18 years old (M = 16.01, SD = 1.29). The results revealed evidence for both congruence and divergence in parent and youth reports, particularly with respect to respondents’ accounts of youth-specific stressors. Discrepancies for youth-specific stressors were associated with adolescents’ negative affectivity, surgency, effortful control, and internalizing problems. Discrepancies for youth stressors may therefore reveal individual differences in emotionality and self-regulation, thus reflecting meaningful variance in adolescents’ functioning.