Early initiation of drinking increases the lifetime risk for substance abuse and other serious health and social problems. An understanding of the predictors of early initiation is needed if successful preventive interventions are to be developed. Surveys were completed by 1009 sixth grade students at the beginning (Time 1) and end (Time 2) of the school year in four schools in one suburban school district. At Time 1, 55/1009 (5.5%) reported drinking in the past 30 days. From Time 1 to Time 2, the percentage of drinkers increase to 127/1009 (10.9%) of whom 101 were new drinkers. In multiple logistic regression analyses, school engagement was negatively associated and peer influence and drinking expectancies were positively associated with drinking initiation. A significant interaction was found between drinking expectancies and parental expectations. Among sixth graders with high drinking expectancies, those with low parental expectations for their behavior were 2.6 times more likely to start drinking than those with parents with high expectations for their behavior. Positive drinking expectancies were significantly associated with drinking initiation only among teens who believed their parents did not hold strong expectations for them not to drink. This finding held for boys and girls, Blacks and Whites and was particularly strong for Black youth. This finding provides new information about the moderating effect of parental expectations on drinking expectancies among early adolescents.