This study of more than 1,300 high school students examined gender differences in the social context of drinking associated with four alcohol problem behaviors (high intensity drinking, binge drinking, driving while intoxicated, and riding with an alcohol impaired driver). A series of analyses treated five social contexts of drinking (Social Facilitation, School Defiance, Stress Control, Peer Acceptance, and Parental Approval) as dependent variables and revealed significant multivariate interaction effects between gender and all four alcohol problem behaviors. Male problem drinkers were more likely to drink in all social contexts than female problem drinkers or non-problem drinkers of both genders. Females were no more likely to drink in the context of Stress Control than males, a finding inconsistent with some previous research. The social contexts of Social Facilitation, School Defiance, and Stress Control were the best discriminators of problem versus non-problem drinkers of both genders (although the order of importance varied by gender and specific problem behavior). Implications for designing targeted interventions are discussed.