In Libellulidae, oocyte production has been assumed to be continuous, with periods of egg-laying interspersed with periods of resting/eating; however, recent work suggests that two types of oocyte production are common: either (a) continuous or (b) step-wise. These are mirrored in the arrangement of the ovarioles in the ovaries. Likewise, two types of mate-guarding behavior have been observed in Libellulidae: (1) non-contact guarding and (2) tandem guarding in which the male either hovers above the female or is physically attached to her during oviposition. Using molecular (mitochondrial and nuclear) data we explored the evolution of female reproductive traits, focusing on ovariole morphology, as well as guarding behavior, in Libellulidae.Continuous egg production appears to have evolved more than once, as have tandem and non-contact guarding. We discuss how the evolution of different ovariole types and guarding behavior may have been influenced by habitat instability, dispersal and crowded oviposition sites; thus, migratory behavior or habitat availability may have been the driving force of ovariole evolution.