Objective: Investigate how women with self-reported endometriosis, polycystic ovary syndrome (PCOS), or no known reproductive disease perform on the Reading the Mind in the Eyes task, a metric of social cognitive empathic abilities, and how these scores are mediated by self-reported pelvic pain, depression levels, and medication use. Design: Cross-sectional. Setting: Online survey. Population: Saskatchewan; mixed ethnicities. Methods: Participants ( n = 342) completed surveys on diagnoses of endometriosis and PCOS, levels of pelvic pain, medications, depression, and cognitive empathy (the Reading the Mind in the Eyes task, RMET). Results: Women with endometriosis showed lower scores on the RMET, compared to unaffected women and women with PCOS. However, among women with endometriosis, higher levels of pelvic pain and higher scores on an index of depression were associated with enhanced RMET performance. Among women with PCOS, medication with spironolactone, an androgen receptor antagonist, was associated with higher RMET scores, compared to women with PCOS who were not medicated or who were taking different medications. Conclusions: Symptoms (including pelvic pain), hormonal correlates, and some treatments of PCOS and endometriosis mediated variation in cognitive empathy.