Male mating strategies are often deployed with regard to female maturity and receptivity, possibly in response to sperm utilization patterns on the part of the female. We examined the pattern of male residency with females during the mating period of the subsocial spider Anelosimus cf. jucundus (Araneae, Theridiidae). We first examined patterns of male cohabitation with naturally occurring penultimate instar and adult females in the field. Males were significantly more likely to be found in association with adult females, rather than with penultimate instar females. Penultimate instar and virgin adult females of known age were then placed into the field and monitored for residency by subsequently marked males. Males were, again, significantly more likely to be found in association with adult females, rather than with penultimate-instar females, although we were unable to determine if this pattern was due to differential arrival or to differential retention of males at adult female web sites. Aspects of A. cf. jucundus natural history, including duration of male residency and frequency of mating in the field, are provided for the first time. We discuss the patterns of male residency in relation to predictions based on sperm utilization patterns by female A. cf. jucundus spiders.