The present study examined how school-age children's communicative decisions are influenced by the situation, their social partner, and their own characteristics (gender, shyness levels, and history of peer relationships). Children (8-12 years old, N=246) imagined themselves in social scenarios (depicted through comics) and indicated the likelihood of using particular communicative options (e.g., truth, lie, sarcasm, or prosocial response). They also completed measures of shyness and past social experiences with peers. Findings revealed gender differences: Boys were more likely to tell the truth when their social partner blundered, and boys demonstrated increased willingness to use sarcasm. Girls, particularly shy girls, reported increased likelihood of responding with prosocial communicative strategies. Children with a history of peer victimization endorsed using more critical comments, whereas those with positive social experiences (particularly girls) reported more prosocial responses. Together the findings provide insight as to how interpersonal and intrapersonal characteristics and contextual factors affect children's communicative choices.