The authors used a daily diary methodology to examine over 60 days how the within-person associations among event stress, alcohol consumption, and desire to drink varied as a function of gender, positive and negative alcohol-outcome expectancies, and avoidant coping in a sample of 88 regular drinkers. Multilevel regression analyses indicated that men who more strongly anticipated positive outcomes or a sense of carelessness from drinking drank relatively more on stressful days compared with low-stress days. Similar results were found predicting desire to drink. Men who anticipated greater impairment from drinking drank relatively less on stressful days. In general, these effects did not hold for women. Little evidence was found for the predicted effects for avoidant coping style, and some results showed that avoidant coping style buffered the exacerbating effects of careless unconcern expectancies.