The present research aims to advance current understanding on how individuals with pathological personality traits construe their day-to-day situational experiences. College students (N = 231) completed a measure of personality pathology, followed by six assessments of everyday situations and anxiety/depression symptoms over two weeks. Multilevel analyses indicated that personality pathology was meaningfully associated with situational experiences. Major findings suggested that situations that entailed aggravations and interpersonal confrontations were associated with negative affectivity, antagonism, and psychoticism. Detached individuals were less likely to experience pleasant and social situations. Exploratory analyses suggested an amplification effect where individuals high on personality pathology were more anxious or depressed when they perceived certain situational features, compared to their low trait counterparts. However, such cross-level interactions constituted a small minority; most personality traits and situations exerted additive effects on symptoms. Situational experiences appear to be driven in part by personality pathology. The exacerbation of daily negative symptoms can be attributed to the joint (largely additive) influence of the trigger situations and pathological personality traits.