The association between career decision difficulties and negative emotions of adolescents has been researched; however, less is known about what moderates this relationship. Based on the transactional model of stress and cognitive theories, it was hypothesized that career decision-making difficulties in high school students are associated with psychological distress and this relationship will be moderated by worry. To test the hypothesis, 384 students from five public high schools in Romania (54% adolescent females, mean age 17.9 years) were assessed. Analyses indicated that career decision-making difficulties (lack of readiness, lack of information, inconsistent information) are associated with negative dysfunctional emotions, and this association is significantly moderated by worry. The results help us to better understand the circumstances in which career decision-making difficulties activate psychological distress.