The colonization of land by plants marked a pivotal transformation in terrestrial ecosystems. In order to adapt to the terrestrial environment, angiosperms, which dominate the terrestrial flora with around 300,000 species, have evolved sophisticated mechanisms for sexual reproduction involving intricate interactions between male and female structures, starting from pollen deposition on the stigma and culminating in double fertilization within the ovule. The pollen tube plays a crucial role by navigating through female tissues to deliver sperm cells. The molecular intricacies of these male-female interactions, involving numerous signaling pathways and regulatory proteins, have been extensively studied over the past two decades. This review summarizes recent findings on the regulatory mechanisms of these male-female interactions in angiosperms. We aim to provide a comprehensive understanding of plant reproductive biology and highlight the implications of these mechanisms for crop improvement and the development of new agricultural technologies.