This thesis examines societal norms and unwritten rules for boys as they mature. It is hypothesized that most boys deal with emotional suppression or dissociation in varying degrees of severity due to traumas during their developmental years. This dissociation creates an inability to express their own emotions adequately and therefore affects their ability to empathize with others. A lack of vulnerability may also be a common challenge among boys society still considers vulnerability weakness. This pattern continues into adulthood and is then perpetuated through posterity and future generations. This thesis explores through a qualitative case study how using art integration in an English classroom, in tandem with teaching a novel written by Patrick Ness and illustrated by Jim Kay, and an emotional education curriculum produced by Yale's Center for Emotions, can give male adolescent students safe opportunities to reassociate with their emotional selves and emotional expressions. Methodologies I used in addition to qualitative case study are interviews of adult men, lyrical sociology in the form of vignettes, and inspiration from an Indigenous methodology of bringing the relationship between researcher and research to the forefront.