Why do we wear masks on Purim? Rabbi Steinsaltz writes about the masks we wear and how sometimes we must wear a mask to “defend ourselves against ourselves.” Paraphrasing Montaigne, he says that were a person to be hung for their thoughts, nobody would escape the gallows. The Talmud teaches that if a person pretends to have an illness in order to collect alms, they will be punished with that illness, a Sage asks and if they wear a mask of piety, what then shall be their punishment? The response: they will not pass away before becoming a saint. We all wear masks, the real question is which mask are we choosing to wear. The Vilna Gaon explained that Purim is the other side of Yom Kippur for the mask we choose on Purim is how we appear unmasked before God on Yom Kippur.