Most studies on masculinity portray men as beneficiaries of male privilege and universally benefiting from a patriarchal system, they knowingly or unknowingly create. Based on an ethnographic inquiry, this article explores untold complex and taken for granted masculinity experiences among men in Kigezi western Uganda (among the Bakiga). We divulge into Bakiga men’s space and unravel how they either adhere to socially masculinity and/or negotiate space to defy the constructed notion of a ‘real man’. Findings indicate that there are vulnerabilities concealed beneath the masculine privilege which is a source of frustration and that pushes some men into relative self-destruction. Men’s vulnerabilities like old age abandonment by children were attributed to impossible social expectations and failure to accept impossibilities, dwindling role model effect, distorted male entitlements and women’s subtle takeover.