In learning contexts, people need to make realistic confidence judgments about their memory performance. The present study investigated whether second-order judgments of first-order confidence judgments could help people improve their confidence judgments of semantic memory information. Furthermore, we assessed whether different personality and cognitive style constructs help explain differences in this ability. Participants answered 40 general knowledge questions and rated how confident they were that they had answered each question correctly. They were then asked to adjust the confidence judgments they believed to be most unrealistic, thus making second-order judgments of their first-order judgments. As a group, the participants did not increase the realism of their confidence judgments, but they did significantly increase their confidence for correct items. Furthermore, participants scoring high on an openness composite were more likely to display higher confidence after both the first- and second-order judgments. Moreover, participants scoring high on the openness and the extraversion composites were more likely to display higher levels of overconfidence after both the first- and second-order judgments. In general, however, personality and cognitive style factors showed only a weak relationship with the ability to modify the most unrealistic confidence judgments. Finally, the results showed no evidence that personality and cognitive style supported first- and second-order judgments differently.