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Previous studies from a wide variety of European countries have demonstrated that low educated adolescents engage more frequently in health risk behaviors compared to high educated adolescents. The present study investigates the mediating roles of parental knowledge and time spent with peers in this relationship. Data were retrieved from a nationally representative sample of 12- to 16-year old Dutch adolescents (N = 5422). Risk behaviors were measured by adolescents' report of daily smoking, binge drinking and cannabis use in the previous month, and sexual debut before age 17. Low educated adolescents indicated that their parents had less knowledge on their whereabouts and reported spending more time with peers than high educated adolescents. Both factors mediated the relationship with health risk behaviors. These results hint to parenting practices and adolescent peer relations as points of reference for prevention and intervention work aiming to reduce educational inequalities in adolescent health risk behaviors. (Contains 2 tables and 1 figure.)