Media driven debates arguing the fate of boys and men are commonplace, but little has been done to bring consensus in finding solutions. This study aims to explore how character strengths may be leveraged to enhance the healthy embodiment of masculinity. A sample of 107 preadolescent and adolescent males participated in this exploratory study of correlations between masculinity measured by the Children’s Personal Attributes Scale and character strengths identified through the VIA Inventory. Secondarily, the subject's self-reported willingness to express emotions was assessed by questions based on the Emotion Expression Scale for Children. Fifteen character strengths were found to be significantly positively correlated with masculinity scale scores and one character strength (humility) negatively correlated with masculinity. Leadership was found to be negatively correlated with emotional expression. Collectively, top strengths were less masculine than expected for students attending an all-boy school. When broken down by grade levels, significant differences were found that support prior studies assessing the differences in character strengths in boys from late childhood to late adolescence. While these findings are specific to the population studied, it may inform continued research in positive masculinity in boys and identify specific ways that character strengths-based interventions can help address the “plight” of boys and men.