We examined whether individual differences in shyness and context influenced the amount of computer-mediated self-disclosure and use of affective language during an unfamiliar dyadic social interaction. Unfamiliar young adults were selected for high and low self-reported shyness and paired in mixed dyads (one shy and one nonshy). Each dyad was randomly assigned to either a live webcam or no webcam condition. Participants then engaged in a 20-minute online free chat over the Internet in the laboratory. Free chat conversations were archived, and the transcripts were objectively coded for traditional communication variables, conversational style, and the use of affective language. As predicted, shy adults engaged in significantly fewer spontaneous self-disclosures than did their nonshy counterparts only in the webcam condition. Shy versus nonshy adults did not differ on spontaneous self-disclosures in the no webcam condition. However, context did not influence the use of computer-mediated affective language. Although shy adults used significantly less active and pleasant words than their nonshy counterparts, these differences were not related to webcam condition. The present findings replicate and extend earlier work on shyness, context, and computer-mediated communication to a selected sample of shy adults. Findings suggest that context may influence some, but not all, aspects of social communication in shy adults.