Pollination and herbivory are both key drivers of plant diversity but are traditionally analyzed in isolation. We investigated real-time evolutionary changes in plant traits over six centuries by employing fast-cycling Brassica rapa plants and manipulating the presence and lack of bumble bee pollinators and foliage herbivores. We found that plants under choice by bee pollinators evolved increased floral attractiveness, but this procedure was jeopardized by the presence of herbivores. Plants under choice from bee pollinators and herbivores developed higher levels of self-compatibility and autonomous selfing, in addition to diminished spatial separation of sexual organs (herkogamy). All in all, the evolution of traits was affected by the interaction of bee pollination and herbivory, highlighting the value of the cross-talk involving both kinds of interactions for plant evolution.