The Gemara (Megillah 28b) states that it is forbidden to look into a wicked person’s face. What exactly are the parameters of this prohibition?
Looking at a Rainbow
The Gemara in Masechet Chagiga (16a) states: “If one looks at a rainbow, his vision will dim, for it is forbidden to look at a rainbow.” When one sees a rainbow, one recites the blessing of “Baruch Ata Hashem Elokeinu Melech Ha’Olam Zocher Ha’Berit Ne’eman Bivrito Ve’Kayam Be’Ma’amaro.”
Rabbeinu David Abudirhem writes: “The Rosh was asked how one is permitted to look at the rainbow as he recites this blessing if the Gemara tells us that if one looks at a rainbow his vision will dim? The Rosh replied that “looking” is not like “seeing” for when looks he gazes and scrutinizes more than one who merely sees.”
We see clearly that whenever our Sages forbade “looking” at something, this refers to staring in which case one focuses on and contemplates what he is observing. However, merely looking at something by passing one’s eyes over it and seeing it for a moment is not forbidden.
Similarly the Sefer Chassidim, second edition, authored by the nephew of the Rosh states: “I have asked my uncle Rabbeinu Asher how is it that people transgress the prohibition of looking at a rainbow while reciting the blessing on it and he answered that “looking” only refers to staring at something intentionally for a prolonged amount of time, but merely gazing at it for a moment is permissible.”
Similarly, the Sefer Yosef Ometz (Yuzpa) writes that although it is forbidden to look at the moon, this only applies when one gazes at it in an analytical fashion; however, merely glancing at it is permitted.
Is this Actually Forbidden?
Thus, the same applies to looking at the face of a wicked person which is only forbidden if one stares at his face for a prolonged amount of time in order to examine it, but to glance at it briefly, for instance, if one is speaking to him and sees the wicked man’s face from time to time, is permissible. The Sefer Torah Temima (Parashat Toldot) rules likewise.
The Torah Temima adds that looking at the face of a wicked person is not actually forbidden, for the Tur and Shulchan Aruch do not mention this law. Rather, our Sages meant that this is something that one should try extremely hard to avoid. He proves this from the fact that the Gemara (Megillah ibid)states that his students asked Rabbi Yehoshua ben Korcha why he merited longevity and he responded because he never gazed into the face of a wicked man. If this were truly prohibited, how could he quote this as the special merit that granted him longevity?
Indeed, the Meiri (Megillah 28a) states that the issue of looking into the face of a wicked man is merely the behavior of the Sages and their students and one should follow suit as much as possible.” However, it is not an absolute prohibition. The Responsa Le’Horot Natan (Vol. 10, Ch. 24) rules likewise.
Luminaries of past generations who needed to meet with kings and tyrants who were haters of Hashem in their places of exile conducted themselves in this way by looking at them sparingly and did not look away demonstratively in order not to look into the face of a wicked man. Once, a terrible enemy of the Jewish people came to meet with Maran zt”l (because there was a need for redeeming captives) and he did not look away, although he did not fixate his gaze on him. This is especially true during our times when doing so will just cause more strife and will not lead to anything productive.
