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Rabban Shimon ben Gamliel provided four different instructions in the Mishnah (4:18). Do not try to appease your friend when he is angry1; do not comfort a person if he has lost a close relative and they are yet to be buried; do not attempt to undo a person's neder at the time he makes a neder; and do attempt to see a person at the time of his sin.
The Tifferet Yisrael first explains the technical reason for each of the statements. Appeasing a person when they are angry is likely to exacerbate their anger. At a moment of loss, if a person senses that others do not feel their pain it will cause further pain. Indeed, the Midrash Shmuel writes that at that time a person does not want comfort. Instead, they want others to feel the pain with him. Regarding the thirds case, when a person makes a neder, they generally want that neder to be in place. The Markevet Mishnah adds that people generally make nedarim in anger. Any challenge at the moment, is likely to close off avenues of potential regret that could be used to undo the neder when he calms down. Finally, when a person stumbles and acts inappropriately, your presence will not help, but only magnify the shame.2
The Tifferet Yisrael continues explaining that the Mishnah recorded four cases of burning emotions. He continues that this advice is not limited to these four situations. Rather any time where people are out of control or overcome by an emotion, is not the time to challenge them. He provides several examples. The first is that arguing with a passionate heretic is more likely to cause him to dig in and assert is his position even more radically. He also adds that on Simchat Torah, Purim or at a wedding, when people are carried away with acting like clowns, it is not the time to attempt to rebuke them. Finally, if someone is in the process of heaping praise on his child or relative and asks your opinion, it is not the time to provide any critical insights. The invitation was simply to add more praise
Irving Bunim explains that having learnt in the previous Mishnah the need to do good in the world, this Mishnah was necessary to temper one's eagerness to do so, so that they do not cause damage despite their good intentions. Similarly, the Yaavetz explains that R' Yaakov had taught that one must pursue good deeds. The Mishnah is necessary to teach that some deeds need to be pursued in a more controlled way.
The Lev Avot (Rabbi Haber) explains that it is appropriate the Rabban Shimon ben Gamliel is the one that taught this Mishnah. Rabban Shimon ben Gamliel was a student of R' Meir who taught, "do not look at the jug, but rather its contents..." The Lev Avot explains that all the matters in the Mishnah are situations where you are not seeing the real person, but rather the outer "jug". They are situations where the person is overcome by emotion. Rabban Shimon ben Gamleil warns that this is not the time to engage with the person, for they are not their true selves.
1 The Ruach Chaim derives this from the fact that the chatat (sin-offering) is offered before the olah. Before the "gift" of the olah can be offered, one must bring a chatat and do teshuva to remove the cause of anger first.
2 The Pirkei Moshe is particular with the words of the Mishnah. The issue is with you coming to "see" him. Just coming to see him, may lead him to suspect that you just want to see him in his fallen state. Nonetheless, one should still attempt to support and console him in his difficult time.
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