Individuals high or low in self-reported social skill were recruited opportunistically. When presented with everyday social scenarios ending with an awkward request or offer, the high social skill participants more often used sophisticated strategies that showed greater consideration for all parties. By contrast, the low skill participants were more reliant on simple strategies including acquiescence or refusal, and the emotional tone of their responses was less positive. Greater reliance on sophisticated rather than simple strategies may be linked to more successful social interactions. The potential implications are considered for understanding everyday performance in skilled individuals and populations with limited social skills, such as those with autistic spectrum disorders.