In recent decades, the oriental armyworm, Mythimna separata (Walker), has caused severe damage to staple grains in China. However, little is known about when M. separata begin their first migration and the role of males in reproduction and migration. Here, the migratory benefits and reproductive costs of flight frequency were examined in adults under laboratory conditions. We found that flying males had a positive effect on ovarian and reproductive development in females who flew for 1–2 nights by comparing two treatment groups (flying and nonflying male groups). Moreover, flying males decreased the flight capacity and flight propensity of females. In contrast, flight for more than two nights by males significantly inhibited ovarian and reproductive development in adult females. Compared with the controls (0 night), male flight for 1–2 nights significantly shortened the preoviposition period but significantly increased ovarian and reproductive development in females. However, male flight for more than three nights significantly inhibited female reproduction and flight capacity. These results indicate that M. separata begin their first migration within 2 days after emergence and fly for two nights. Prolonged flight times can result in significant reproductive costs. Females initiated their first migration earlier than males due to a stronger flight capacity. These observed findings will be useful for forecasting and monitoring population dynamics to prevent outbreaks of M. separata and reduce crop losses.