Previous work suggests that, in some circumstances, cognitive processes can be facilitated by engaging related processes. In this study, we investigated whether engaging in mentalizing during reappraisal, an emotion regulation strategy, would lead to greater changes in affect and reduce the perceived difficulty of reappraisal. We trained participants to reappraise negative pictures through reinterpretation. For some trials, participants generated reappraisals as they would for themselves, while for others, they mentalized, generating reappraisals while taking the perspective of a specific, close friend viewing the pictures. Participants rated their own negative affect and the perceived difficulty of reappraisal both online (i.e., during the task) and immediately posttask. We observed different results for the impact of mentalizing through online and retrospective (posttask) reports. As predicted, participants retrospectively reported that reappraisal while mentalizing was less difficult and decreased their negative affect. Online, however, some evidence suggested that reappraisal while mentalizing was perceived as more difficult and resulted in greater negative affect. Overall, we did not observe a facilitative effect of mentalizing on reappraisal, but in retrospect, individuals may have believed that mentalizing was helpful for reappraisal. More broadly, these findings emphasize the importance of the cognitive context of reappraisal and different types of self-report. (PsycInfo Database Record (c) 2023 APA, all rights reserved).