Adolescent problem behaviors are an important area of investigation because of the long-term implications of engaging in risky and delinquent behaviors. Past research has focused on overt aggression and peer rejection as an indicator of negative outcomes, without accounting for relational aggression. This research hopes to expand on our understanding of the pathways to adolescent problem behaviors by longitudinally assessing 377 high school students from a Northeastern town over the course of grades 10, 11, and 12. SEM analyses indicate that overt aggression continues to be a strong indicator for negative outcomes and relational aggression is an important indicator of both positive and negative outcomes above and beyond overt aggression via moderation by peer rejection. While the use of relational aggression paired with low levels of peer rejection indicated the highest risk of negative outcomes, higher levels of peer rejection conferred a small decrease on rates of the measured outcomes. Future studies combining ideas from research on both delinquency and popularity are needed to fully understand the impact of relational aggression on adolescent outcomes.