Abstract A trade‐off between flight and reproduction has been well studied in wing dimorphic female insects but less attention has been given to this trade‐off in males. In this study, the authors analysed the differences in the calling behaviours of long‐winged (LW) and short‐winged (SW) male Velarifictorus aspersus crickets. Furthermore, the authors examined the effects of flight and wing dealation on the calling behaviour of LW males, as well as female preferences regarding the calling songs of males. The results showed that SW males sang more often than LW males during the first 9 days after emergence, but there were no significant differences in the song characteristics of SW and LW males. A flight of 5 min increased the singing time by LW males without changing the song characteristics, but a flight of 30 min or wing dealation increased both the singing time and chirp number per song. In binomial choice trials, female crickets did not prefer SW calling song to unflown LW calling song. But when LW males had either flown 30 min or been dealated, females preferred LW to SW calling song. Therefore, LW males may attract fewer females than SW males when they are preparing for dispersal, but this reproductive disadvantage may be absent during dispersal and the settling stage.