During their teenage years, adolescents often engage in risk behaviors as they search for their identity and strive for independence from their parents. A secondary data analysis was performed on findings from a larger study that addressed parental monitoring of adolescents. Parent-adolescent open communication, parental monitoring, parent-adolescent communication, and comfort communication were studied to test for a relationship to risk behaviors. The risk behaviors examined were delinquent / drug use behaviors, “sneak” behaviors, and minor rule breaking behaviors. The significant findings were, for females, communication comfort and the interaction between open communication and communication comfort predict less risk behavior engagement, and for males, problem communication predicts delinquent / drug using behaviors. Further studies, with larger, more representative samples, need to be done in order to draw further conclusions about the influence of parent-adolescent communication and adolescent risk behavior.