This paper compares rabbinic and patristic stories of repenting prostitutes from late antiquity, showing that while some narrative structures remain fixed in both traditions, namely, the prostitute's story framed within that of a man, a competition between the man and the prostitute over the leading role, the perpetually open path to repentance, and more, other structures vary or take a different meaning. These include the gender identity of the desiring subject, the spiritual principle behind the story, the gender of the repentant, and his/her fate. The article offers a definition of “the repenting prostitute” as a tale type, as well as close readings in its rabbinic ecotype, in order to understand if, how, and why the Jewish and Christian traditions take different paths of meaning-making using similar narrative forms.