Adolescent bullying perpetration has previously been associated with dating benefits and costs in the short- and long-term, yet it is unclear how early temperament traits facilitate these associations. Therefore, the developmental pathways from temperament in early adolescence to bullying perpetration in middle adolescence and to dating outcomes in late adolescence were examined. Participants included 463 individuals who completed self-report measures on temperament traits at age 12, bullying perpetration at age 14, dating outcomes at age 19, and were in a romantic relationship at age 19. Findings from a path analysis revealed that an early adolescent temperament trait reflecting difficulty with self-regulation (i.e., lower inhibitory control) was associated with middle adolescent bullying perpetration and bullying perpetration was associated with late adolescent dating benefits (i.e., more dating partners) and costs (i.e., higher dating aggression perpetration). Lower inhibitory control also had significant indirect associations to the late adolescent dating outcomes through middle adolescent bullying perpetration. Findings suggest that although a temperament trait can facilitate adaptive dating outcomes through bullying, it can also come at a cost for romantic relationships. Results highlight the importance of early tailoring of bullying interventions to the self-regulatory difficulties of youth to prevent adverse long-term outcomes and to also recognize the challenges of developing interventions for behavior that can result in benefits.