This study adopted a self-presentation perspective to examine cognitive factors involved in maintaining social anxiety in men in heterosexual situations. The self-regulatory appraisals of 25 socially anxious and 25 nonanxious men were compared using a modified version of the Articulated Thoughts in Simulated Situations (ATSS) procedure (Davison, Robins, & Johnson, 1983). Subjects viewed videotapes of two enacted situations between a male actor and a female actor which differed on whether the individuals were strangers or acquaintances. The subjects were instructed to identify with different male actors who depicted contrasting styles of self-presentation. In contrast to nonanxious men, socially anxious subjects consistently made pessimistic self-appraisals, articulating more negative self-focused thoughts, and displaying negative self-other biases. However, nonanxious men showed equivalent levels of self-focused negative thoughts in response to representations of a protective style of self-presentation. Unexpectedly, for all subjects, the less intimate first meeting situation elicited more negative self-focused thoughts than did the more intimate dating situation. The findings are discussed in terms of self-regulatory components of self-presentational styles and the implications for treatment of social anxiety.