Despite broad interest, experimental evidence for gender differences in social abilities remains inconclusive. Two important factors may have limited previous results: (i) a lack of clear distinctions between empathy (sharing another's feelings), compassion (a feeling of concern toward others), and Theory of Mind (ToM; inferring others’ mental states), and (ii) the absence of robust, naturalistic social tasks. Overcoming these limitations, in Study 1 (N = 295) we integrate three independent, previously published datasets, each using a dynamic and situated, video-based paradigm which disentangles ToM, empathy, and compassion, to examine gender differences in social abilities. We observed greater empathy and compassion in women compared to men, but found no evidence that either gender performed better in ToM. In Study 2 (n = 226) we extend this paradigm to allow participants to engage in prosocial donations. Along with replicating the findings of Study 1, we also observed greater prosocial donations in women compared to men. Additionally, we discuss an exploratory, novel finding, namely that ToM performance is positively associated with prosocial donations in women, but not men. Overall, these results emphasize the importance of establishing experimental designs that incorporate dynamic, complex stimuli to better capture the social realities that men and women experience in their daily lives.