Asynchrony in reproductive behavior may contribute to reproductive isolation among sympatric species. While the 38 cryptic species of the genus Laupala are primarily distinguished on the basis of variation in pulse rate of male calling songs, additional phenotypes, such as asynchrony in reproductive behavior, may contribute to reproductive isolation in this genus. Here we document similarities and differences in the diel timing of two reproductive behaviors, male singing activity and insemination events. Asynchrony in the diel timing of male singing behavior was observed between two sympatric species, Laupala cerasina and Laupala paranigra, in the field. An interpopulational comparison within L. cerasina did not reveal variation in diel behavior patterns of singing between two locations. Asynchrony in the timing of copulation and sperm transfer between L. cerasina and L. paranigra was documented in the laboratory. The observed pattern of asynchrony in both the field and laboratory could have arisen in a number of ways. One possibility is that species diverged in sympatry because of interspecific interactions, producing a pattern of reproductive character displacement. Alternatively, the observed asynchrony in reproductive behavior may have played a role in the process of community assembly within this recently diverged cricket genus. The presence of interspecific variation and the absence of intraspecific variation revealed by our study do not support a pattern of reproductive character displacement for diel reproductive behavior, suggesting that the differences seen between species were not caused by recent species interactions.