The goal of this study is to explore how humor and stigma affect comforting quality and reappraisals when seeking support for a mental health condition (MHC). Participants (N = 159) were asked to describe a time they sought support for their MHC. They then completed a survey to assess their self-stigma, use of humor when seeking support, and support outcomes. Stigma positively predicted the use of negative humor when seeking support for a MHC. Stigma also negatively predicted coping efficacy; however, this relationship became positive when mediated by a participant's use of negative humor. Positive humor positively predicted coping self-efficacy and empowerment, which in turn predicted comforting quality. The results address a gap in the literature that does not examine the use of humor when seeking support. The findings also extend knowledge on how humor and stigma affect reappraisals of MHCs.