Experience effects on mating have been implicated as important factors that can account for some of the variability in responses by prospective mates. Previous studies have demonstrated that sexual experience and learning can play significant roles in female choice; however, few studies have concentrated on experience effects in males. Using a partially sex-role reversed cellar spider, Pholcus phalangioides, in two laboratory experiments, we addressed the importance of male experience with (1) nonvirgin female cues associated with silk and (2) virgin females on a suite of male behaviors associated with mating. We discovered that males experienced with female silk and associated cues courted nonvirgin females for a longer duration than inexperienced males. Courtship latency and courtship duration had significant effects on mating success in trials involving inexperienced, but not experienced males. Female leg length affected the mating success of experienced, but not inexperienced males. Interestingly, no males mated twice when sequentially presented with two virgin females over a 24 h period, and most mated males (92%) failed to court the second female. Our findings suggest that male experience affects mating behaviors with both mated and virgin females and that males may be sperm limited.