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Individuals with elevated social anxiety appear particularly vulnerable to experiencing alcohol-related problems. However, research has thus far failed to identify factors that seem to account for this relationship. The present study utilized a measure designed to assess alcohol-related behaviors related to social situations previously identified as anxiety-provoking among those with elevated social anxiety. The Drinking to Cope with Social Anxiety Scale (DCSAS) assessed alcohol-related behaviors in 24 social situations and was comprised of two subscales: Drinking to Cope in Social Situations and Avoidance of Social Situations if Alcohol was Unavailable. Both DCSAS scales demonstrated adequate internal consistency and were significantly, positively related to number of alcohol-related problems. Individuals with clinically meaningful social anxiety (n = 60) achieved higher scores on both DCSAS subscales compared to those with lower social anxiety (n = 60). Importantly, the DCSAS scales mediated the relationship between social anxiety group classification and alcohol-related problems. Results highlight the importance of contextual factors in assessing alcohol-related behaviors among high-risk populations.