Self-fertilization, prevalent in plants, is typically divided into three modes - prior, competing, and delayed selfing - based on the timing in which it occurs. Flower longevity affects both the opportunity for pollination and the resources allocated for fertility, and thus may influence the selection on different modes of self-fertilization. Additionally, selfing causes fertilization to depend less on pollinators, which may also influence the evolution of flower longevity. Using game-theoretical models, I investigate how inbreeding depression and the pollination environment influences the coevolution of the three modes of self-fertilization with flower longevity. Invasion of prior selfing allows the subsequent evolution of shorter flower longevity, and thus is favored over competing selfing. Prior selfing can also invade even under high inbreeding depression when the pollen deposition rate is low, but is inhibited by a higher level of delayed selfing. In general, the evolution of selfing decreases flower longevity, and reveals asymmetric effects of pollen deposition and removal on flower longevity. This study suggests considering realization of selfing and outcrossing as concrete processes by incorporating flower reproductive strategies (e.g., flower longevity) and pollination ecology (e.g., accrual rate) may offer better understanding of the evolution of mating systems and flower reproductive traits.