This article explores the use of gender in the Religious History, demonstrating the multiple ways that Theodoret of Cyrrhus marked ostensibly male characters with traits associated in ancient medical literature with female bodies. Beyond simply depicting ascetics as extraordinary human beings, these complexly gendered portraits more importantly served as expressions of an argument Theodoret advanced elsewhere: that men and women shared a common human nature. Based on these observations, the article then offers an interpretation of the two bodily examinations performed upon Theodoret’s most influential character, Simeon the Stylite, namely that these scenes were carefully narrated to suggest that they were examinations of a female body. In conclusion, I argue scholars should consider the peculiar uses of gender in each ancient representation of early Christian asceticism, rather than assume early Christian texts only associated masculinity with excellence in ascetic practice.