Diospyros sericea is a tree/shrub species considered dioecious and broadly distributed in Brazil. Despite its importance for niche composition in a range of ecosystems, there is little knowledge about this species, and so far no study has analyzed its sexual system. We aimed to investigate dioecy expression in D. sericea through sexual dimorphisms in its phenology and floral biology. We analyzed the phenological events over a year and studied floral biology traits (morphology, flower development, floral resource, floral attractants supply, viability of pollen, and stigma receptivity) in both male and female plants. D. sericea presents typical features of dioecious plants like well-established primary and secondary dimorphisms that contribute to its reproductive success. However, we also identified fruit development in what should be structurally male individuals. We suggest that the evolutionary pathway leading to the observed phenomenon may be the existence of subdioecious populations with “inconstant males”. Although our data prevented us from making further assumptions about the origin of this trait, the study contributes to future analyses towards unraveling the enigma of dioecy not only in D. sericea but in other Diospyros species.