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This study identifies trajectories of dating from sixth to twelfth grade and describes the academic performance (teacher-rated study skills and high school dropout) and self-reported drug use associated with these trajectories, in a diverse sample randomly selected in sixth grade. Using a group-based, semiparametric procedure, we identified four dating trajectories: low (16%), increasing (24%), high middle school (22%), and frequent (38%). Students in these latter two groups had significantly worse study skills, were four times more likely to drop out of school, and reported twice as much alcohol, tobacco, and marijuana use than students in the low and increasing dating groups. This study highlights the diversity of dating trajectories and some of the risks associated with early dating.