“And you shall not corrupt the land…” (Bamidbar 35:33).
The Sifri writes that this verse is the source of the prohibition against flattery. The Meohr Yisroel states that flattery is forbidden unless one wishes to bring an individual who has become estranged from Judaism closer to Hashem.
Mishlei states, “A person who tells a wicked person, ‘You are righteous’ will be cursed by the people and detested by the nations. Those who criticize should be pleasant, and good blessing will come upon them” (24:24-25). R’ Shlomo Agazi says that although flatterers are despised by Hashem – indeed, the Gemara (Sotah 42a) says, “Four classes of people will not receive the Divine Presence [and among them are] the class of flatterers, as [Iyov 13:16] says, ‘A hypocrite will not come before Him’” – flattering can sometimes be a mitzvah.
R’ Shlomo Agazi elaborates that flattering someone – praising his intelligence and character, for example – is permissible to finesse a reproach. In other words, one can tell someone that it does not behoove a person of his character to conduct himself in such an inappropriate manner. A person who criticizes in this manner has fulfilled the exhortation of “those who criticize should be pleasant.” He also gives great satisfaction to Hashem and is blessed by Him, says Tanna D’Bei Eliyahu.
May one flatter a Jew whose actions are very much not in consonance with the Torah? The Binyan Tzion has a fascinating teshuvah that is relevant to this question. He writes that we may not use wine touched by a person who consistently profanes the Shabbos since profaning Shabbos is like denying the existence of the Creator and His creation of the world.
However, notes the Binyan Tzion, perhaps we should distinguish modern-day Shabbos violators from Shabbos violators of yore. Due to widespread chillul Shabbos and public ignorance, some people pray on Shabbos and even make Kiddush – in effect, recognizing the Creator and acknowledging His creation of the world – and then fail to adhere to the laws of Shabbos. This behavior seems to put them in the category of “tinok shenishba” (one who was taken into captivity from a young age) rather than in the category of “mumar” (one who violates Shabbos or serves avodah zarah on purpose).
From this teshuvah, it would seem that one could be lenient and even flatter someone whose behavior does not coincide with the Torah’s commandments.
We learn in Iyov (36:13), “And those who flatter will bring out Hashem’s anger; they should not cry out to Him when He afflicts them.” The Sefer Divrei Torah comments that one would think a charming individual is congenial and therefore able to facilitate peace in the world. Peace, of course, is extraordinarily important. As we know, the Torah allows the truth to be altered for the sake of peace. Even Hashem’s name is erased to create peace between husband and wife (in the case of the sotah). Why, then, is flattery so bad?
The answer is that habitual dishonesty is different. The trial of a sotah is very rare. It would be most unusual for Hashem’s name to be erased to clear a sotah’s name even once in a lifetime. Sefer Iyov is referring to an individual for whom flattery is habitual and chronic. Even for the sake of peace, one may not establish flattery as a way of life.
Flattery is such a grievous aveirah that Tosafos even discusses whether flattery is permissible in an emergency – for example to save a life. Tosafos argues that it is permissible (indeed, obligatory), but the fact that he even poses the question reveals how severe a sin flattery is.
And yet, some people do not realize its severity and do not think they need to repent for flattering people. For that reason, Rabbeinu Yonah examines the topic of flattery in various situations in his Shaarei Teshuvah.
Approximately 40 years ago, R’ Ovadiah Yosef gave a lecture every Friday night in Yeshivat Porat Yosef. Hundreds of people would gather to listen to his words of mussar and inspiration. One Friday night, during the lecture, a Jew walked in with his bicycle. He inquired about the gathering and was told that people from all walks of life come to hear R’ Ovadiah speak. Curious, he parked his bike in a corner and sat down to listen.
He was inspired by and very much enjoyed the lecture, and returned the following Friday night. After attending for a number of weeks, he arrived early one Friday night and sat down in the first row, right in front of the lectern. Slowly, but surely, he did teshuvah. He corrected his ways, married a G-d-fearing woman, sent his children to yeshiva, and established a true Torah home.
No one had admonished him when he came with his bicycle. No one had made him feel bad that he didn’t realize it was inappropriate to bring a bicycle into shul. He was greeted warmly, and when he took a front seat, usually reserved for the kehillah’s more distinguished members, no one said a word. As a result, many children and grandchildren bring great satisfaction to Hashem.