The present study examined 85 adult offspring of alcoholics (FH+) and 68 comparison subjects without a family history of alcoholism (FH-) in order to address three questions: (1) Does the relation between hassles and uplifts and drinking differ by gender and/or family history of alcoholism? (2) Do hassles and uplifts and/or generalized outcome expectancies (dispositional optimism and pessimism) moderate the relation between having a family history of alcoholism and drinking behaviors? (3) Do hassles and uplifts and outcome expectancies interact to influence drinking behaviors? The pattern of relations between hassles and uplifts and drinking behaviors and between outcome expectancies and drinking behaviors differed by family history and gender. Hassles were related to increased alcohol consumption for FH+ men only, whereas outcome expectancies were related to indicators of problem drinking for FH+ women only. When the moderating influences of hassles and uplifts and outcome expectancies were examined, both hassles and pessimism were found to moderate the relation between family history and drinking behaviors. In addition, hassles and uplifts and outcome expectancies interactively influenced this relation. These results emphasize the need to examine further both individual and contextual processes in studies examining the risk of the development of alcoholism.