The relation between social anxiety and hedonic activity remains poorly understood. From a self-regulatory perspective, we hypothesized that socially anxious individuals experience diminished positive experiences and events on days when they are unable to manage socially anxious feelings adequately. In this 21-day experience-sampling study, we constructed daily measures of social anxiety and emotion regulation. Greater dispositional social anxiety was associated with less positive affect and fewer positive events in everyday life. Among individuals defined as socially anxious from their scores on a global self-report measure of social anxiety, the number of positive events was lowest on days when they both were more socially anxious and tended to suppress emotions and highest on days when they were less socially anxious and more accepting of emotional experiences. Irrespective of dispositional social anxiety, participants reported the most intense positive emotions on the days when they were both least socially anxious and most accepting of emotional experiences. Possible clinical implications are discussed.