In many species, males defending mating territories face a trade-off between survival and reproductive opportunities when escaping predators. To avoid missing mating chances, males often take greater risks in the presence of females. Because female receptivity varies seasonally, males that adjust their escape decisions according to the reproductive period may gain a selective advantage, yet the evolution of this behavioral modulation remains unexplored. We developed an individual-based simulation model to investigate how different escape strategies evolve. Males adopted one of four strategies: (i) adjusting flight initiation distance (FID) based on female presence, (ii) modifying FID according to the reproductive period, (iii) adjusting FID based on both female presence and reproductive period, or (iv) maintaining a fixed FID. Our results show that males that modulate their FID in response to female presence or during the reproductive period are favoured under conditions where delaying escape significantly increases the likelihood of retaining females, and when the correlation between FID and survival is weak. In contrast, when FID strongly predicts survival and delayed escape has a limited effect on female retention, males with fixed FID dominated the population. These results highlight the significance of context-dependent flexibility in shaping the evolution of escape decisions.