Dioecy in plants is relatively common (~6% of all plant species) but the evolutionary transition from hermaphroditism to separate sexes in plants is not always fully understood. One of the plant genera that offers an excellent opportunity to study this process is Schiedea (Caryophyllaceae), a Hawaiian endemic genus consisting of 34 species. Schiedea exhibits an extremely diverse range of breeding strategies, varying from insect to wind pollinated, hermaphroditic to dioecious, and out-crossing to self-pollinating. Understanding breeding system evolution in Schiedea is of great importance as it can help to illuminate the evolution of separate sexes in plants, especially on oceanic islands where pollinators are fewer than on the mainland.  Previous phylogenetic studies suggest that the ancestor of Schiedea was hermaphroditic, and separate sexes have likely evolved multiple times, coinciding with the evolution of wind pollination in drier Hawaiian habitats. However, because of poor resolution in some parts of Schiedea phylogeny in previous work, the evolutionary transition between sexes is not fully understood. To investigate this question in greater detail, we are using targeted sequence capture to sequence ~1000 nuclear genes to reconstruct a well-built phylogeny of all extant Schiedea species. So far, we have data from 234 accessions representing multiple populations of almost all taxa plus 10 outgroups. The much larger number of genes should aid in resolving the relationships among Schiedea, which will allow for reconstruction of breeding system evolution with much greater confidence.  Ultimately, this study will contribute to our understanding of plant evolution and diversity, providing critical insights into the fascinating and complex process of reproductive evolution. Furthermore, our results will also have great implications for the conservation and management of the genus Schiedea, which is threatened by habitat destruction and invasive species.