Understanding the interrelation among problem behaviors and their change over time is fundamental for prevention research. The Healthy Teens Longitudinal Study followed a cohort of adolescents from Grades 6–12. Prior research identified two distinct trajectories of perpetration of physical dating violence: Low and Increasing. The purpose of this study was to examine whether adolescents in these two trajectories differed longitudinally on other problem behaviors: (1) suicidal ideation and attempts, (2) weapon-carrying and threats with a weapon, and (3) substance use, particularly alcohol and marijuana. The sample consisted of 588 randomly-selected students (52% males; 49% White, 36% Black, 12% Latino). Students completed a self-reported, computer-based survey each spring from Grades 6–12. To examine significant differences by perpetration of physical dating violence trajectory, we used Chi-square test and generalized estimating equations modeling. Across most grades, significantly more students in Increasing than in the Low trajectory reported suicidal ideation and attempts, carried a weapon, and threatened someone with a weapon. Adolescents in the Increasing trajectory also had higher trajectories of alcohol use, being drunk, and marijuana use than those in the Low trajectory. All differences were already significant in Grade 6. The difference in the rate of change between groups was not significant. This longitudinal study highlights that problem behaviors—physical dating violence, suicidal ideation and attempts, weapon carrying and threats, marijuana and alcohol use—cluster together as early as sixth grade and the clustering persists over time. The combination of these behaviors poses a great public health concern and highlight the need for early interventions.