Understanding mating behavioral sequence helps us identify the mechanisms of mate assessment and choice, and better evaluate behavior-based pest control strategies. Here we describe the mating behavior of Cnephasia jactatana Walker whose females release a sex pheromone, and determine the effect of male mating status on reproductive success. The mating sequence starts when males approach females and display courtship behavior with antennation and fanning wings. Both males and females may end a mating attempt at any stage of the sequence. Both sexes assess their mates from the initial contact to copulation. Females appear to be choosier at the early and mid-stages than at the late stage of the sequence. Virgin males approach and court females significantly earlier than nonvirgin males. As compared with nonvirgin males, virgin males are ≈1.6 times more likely to approach and 1.8 times more likely to court females, and four times more likely to achieve mating. This may be attributed to depletion of sperm and accessory gland materials and reduced ability to respond to female sex pheromones in nonvirgin males. The number of attempts by males to acquire mates may be one of the traits that females assess before choosing their mates.