The ancient rabbinic debate over how to engage potential converts hinged on a crucial pedagogical question: should teachers meet seekers where they are, or demand strict adherence to tradition from the outset? A fascinating Talmudic narrative illuminates this tension through three gentiles who approached Rabbis Shammai and Hillel with seemingly outrageous conversion requests - one demanding to learn only Written Torah, another asking to master Judaism while standing on one foot, and a third insisting on becoming High Priest. Through detailed textual analysis and interpretative expansion of the compressed Talmudic account, Gershfield reveals how Hillel's patient, individualized approach succeeded where Shammai's strict rejection failed. The methodology combines close reading of the original Talmudic text with contextual speculation about the cultural backgrounds and motivations of each prospective convert. While both rabbis possessed comparable scholarly expertise, Hillel's distinctive ability to perceive genuine spiritual seeking beneath apparently inappropriate demands proved transformative. His success demonstrates a fundamental principle that remains relevant for modern religious education: effective teaching requires understanding the questioner's cultural context and personal journey rather than merely addressing surface-level inquiries in their pursuit of divine truth.