The events that occur during reproduction play a critical role in determining the distribution of genetic and phenotypic variance within populations and thus their potential to adapt and persist. Understanding the forces shaping the evolution of mating patterns and the diversity of traits that influence mating success in the natural world is a fundamental problem in evolutionary biology. Plants, in particular, show an impressive amount of diversity in floral form and the degree to which they outcross or self-pollinate. In this seminar, I will share a series of empirical and modeling studies investigating how the pollination environment drives the evolution of floral traits that promote either outcrossing or selfing.