People sometimes seek to convey discrepant impressions of themselves to different audiences simultaneously. Research suggests people are generally successful in this “multiple audience problem.” Adding to previous research, the current research sought to examine factors that may limit this success by measuring social anxiety and placing participants into situations requiring them to either establish or preserve multiple impressions simultaneously. In general, participants were more successful when preserving previously conveyed impressions than when establishing impressions for the first time. In contrast, social anxiety did not affect multiple audience success. In all, this research offers valuable insight into potential challenges that people face in many social situations.