Objectives. Patients with social anxiety disorder (SAD) not only fear social rejection, but accumulating evidence also shows that they are indeed less liked than their non-anxious counterparts. Three factors are hypothesized to play a role in this social anxiety-social rejection relationship: (1) social performance; (2) elicited negative emotions, and (3) perceived similarity. Method. Patients with SAD (N = 63) and control participants (N = 27) were observed during a 5 minutes 'getting acquainted' conversation with a male and female confederate who rated their social performance. Video-observers rated their own negative emotions and perceived similarity with the patients, while other video-observers rated their wish to engage in future contact with them (a measure of social rejection). Results. Analysed by way of structural equation modelling (SEM), the results supported the social anxiety-social rejection relationship. More specifically, poor social performance was associated with perceived dissimilarity ratings and mediated by evoked negative emotions, both of which were in turn associated with social rejection. Conclusion. These results suggest that a sequence of events links social anxiety to social rejection. Treatment should aim to improve social performance and perceived similarity to reverse SAD's vicious, negative interpersonal cycle.