The central task of any evolutionary biologist is understanding what lead to the evolution and diversity of life on earth. Thus, the ecological, spatial, genetic, and historical, drivers of vascular plant speciation have been extensively investigated over the last century, leading to the accumulation of genomic data for an increasingly large number of vascular plant taxa. Emerging from this growing body of work is the recognition that hybridization has played (and continues to play) a fundamental role in vascular plant evolution. In this way, gene flow (both hybrid speciation and introgression) is an evolutionary process that is inextricably linked to speciation—it’s not an aberrant phenomenon that occasionally plagues unlucky systematists. Thus, we should not only be asking “How frequently does hybridization occur, and what are its evolutionary consequences?”, but also “Under what conditions are evolutionary trajectories of lineages driven towards hybridization?” The probability of hybridization and its success should depend on a combination of: (a) the historic and geographic context under which the parental species evolved, (c) the historic and geographic context under which the parental species hybridized, and (d) relevant life-history traits of the parental species. We use a combination of available trait, phylogenetic, and distribution data to hypothesize that: 1) Hybridization will be more frequent in temperate versus tropical regions (even when accounting for phylogeny); 2) Hybridization will be more frequent in plants with certain life history characteristics; 3) Current rates of congener co-occurrence differentially predict hybridization frequency depending on region/life history traits. In general, this study emphasizes the fact that, like divergence, gene flow is a regular evolutionary event predicted by historical, geographic, and phylogenetic factors.