Research on how dark personality traits develop and relate to risky behaviors and family relations during adolescence is scarce. This study used a person-oriented approach to examine (a) whether distinct groups of adolescents could be identified based on their developmental profiles of callous-unemotional (CU), grandiose manipulative (GM), and dysfunctional impulsivity (DI) traits and (b) whether these groups differ in their problem behaviors and parent–adolescent relationship quality. Latent class growth analyses on 4-wave data of 1,131 Dutch adolescents revealed 3 personality profiles: (1) a dark impulsive group (13.9%), with high scores on all 3 traits (CU, GM, and DI) that were stable over time; (2) an impulsive group (26.1%), with high and increasing levels of impulsivity and relatively low scores on CU and GM; and (3) and a low risk group (60.0%), with relatively low levels on all 3 personality characteristics, with impulsivity decreasing over time. Compared with adolescents in the low risk group, adolescents in the dark impulsive and impulsive groups reported higher initial levels of substance use, sexual risk behaviors, permissive sexual attitudes, parent–adolescent conflict, and lower parent–adolescent satisfaction, as well as greater increases in sexual risk behavior over time. Compared with adolescents in the impulsive group, those in the dark impulsive group showed the highest levels of risk behaviors. Hence, dark personality traits coupled with impulsivity may be indicative of an earlier and more severe trajectory of problem behaviors that may differ from the trajectory of youth who are only impulsive.