Recent findings suggest that emotional instability and psychological disorder rate in prison is three times higher than in the general population. Prisoners – especially males – are also at increased risk of all-cause victimization including violence and self-harm. This research sought to identify and analyze the emotions that incarcerated males at the Correctional Institutions in St. Vincent and the Grenadines have had and or were encountering, as well as the manner these emotions were being dealt with. It also sets out to ascertain some of the factors that were playing prominent roles in the lives of incarcerated males regarding those emotions. Up to date, there has been no research work done on males and their emotions in St. Vincent and the Grenadines nor any study regarding inmates in the correctional institution. The administration of a short questionnaire formed the quantitative collection instrument, which provided data from 150 inmates. The data analysis was performed via SPSS, and the findings point to a cross-section of relational factors that are relevant to males and their emotions (namely, abuse, crying, bonds, and suicidal thoughts). It was found that males are struggling emotionally with understanding their identity and are inadvertently pressured to adhere to societal directives by restricting their emotional expression.