Many have examined the desirability and mate competition tactics of adults higher on psychopathy using cross-sectional data, but few have studied the longitudinal associations between the lower-order factors of psychopathy (e.g., primary and secondary psychopathy) with indices of mating behavior in adolescents. More work is also needed to unravel how psychopathic youth outcompete rivals for mates. Delinquency has long been associated with dating and sexual behavior in adolescents, which may help to explain the competitive success of youth higher in psychopathic traits in vying for mates. We used cross-lagged panel modeling with three waves of data from a randomly drawn sample of 514 Canadian adolescents who provided annual self-reports of primary and secondary psychopathy, delinquency, and dating involvement from Grades 10 to 12 (15–18 years of age). Constructs were temporally stable. Secondary psychopathy and delinquency had positive within-time correlations with current dating status in Grade 10. A cross-lagged pathway from delinquency to dating involvement was supported from Grade 10 to 11, which replicated from Grade 11 to 12. However, this effect was specific to boys and not girls. An indirect effect also emerged whereby secondary psychopathy in Grade 10 increased the likelihood of being in a dating relationship in Grade 12 via heightened delinquency in Grade 11.