The human tendency to seek connection and love is often countered by deep psychological wounds, particularly attachment wounds that manifest in avoidant or insecure styles. In recent years, anti-monogamy attitudes have gained popularity, sometimes viewed as a pathway to personal freedom or more authentic expressions of human relationships. However, a critical lens reveals that these attitudes can also be a manifestation of self-avoidance, allowing individuals to dodge the painful, yet necessary, introspection that monogamous intimacy demands. Beneath this rejection of monogamy often lies unhealed trauma, fear of vulnerability, and avoidance of accountability for one’s inner emotional landscape. This essay explores how unresolved psychological wounds, such as self-victimization, blame-shifting, and insecure attachment styles, contribute to this phenomenon, and considers the spiritual, psychological, and relational consequences of such avoidance.