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Wonderful question. You describe two levels but there might even be three What parents ask for or command What parents want or hint What parents need but don't ask/hint I believe the answer is your level 2 but in certain cases even level 3. As brief context, the mitzvah of honoring once parents comes from two psukim "Honor your father and mother" ...


Yeshivat Hesder Yerucham has a long discussion on Kibud Av V'Aim. It mentions in the name of Harav Yaakov Ariel that Midas Chasidus is not Doche Kibud Av V'Aim. הוא מסביר שזה תלוי בשאלה האם הידור מצווה דוחה כיבוד אב ואם, שכן במצוות מלחמת מצווה יוצאים ידי חובה גם כטוראי פשוט. הרי"א מוכיח שמידת חסידות לא דוחה כבוד אב ואם, וכן מנהג.


As discussed previously: Yoreh Deah 240 siman 8 says that kibud av v'em does not override "any torah or rabinic commandment." Beis Lechem Yehuda there comments: If a son knows that his parents fret when he fasts, he should not fast any days that are not obligatory. The Pischei Teshuva talks about wearing black as a sign of mourning, or saying ...


I'll add that the Ben Ish Chai gave two reasons: Everything Yaakov said was said in ruach hakodesh, so he was required to speak in a very exact way, it wasn't just his own free way of speaking. Yaakov did say something like "my great, honored, father, teacher, etc.", but the Torah puts it down eventually as what is needed for future generations, in a ...


The obligation of kibbud av ve'em is to be to your parent what your parent construed you to be when you were a child. Subsequently any action or feeling that as a child you would have impulsively done is a chiyuv to do for your parents otherwise you will abnegate that expectation. See also the Mesillas Yesharim who chooses a son performing the parent's ...


When the Chasam Sofer was about 13 he gave a shiur in which he argued with his grandfather. His father slapped him for his chutzpah. Reb Nosson Adler consequently forbade the Chasam Sofer to speak to his father for the rest of his life. So you see extra steiging trumps kibbud av.


I saw in a Sefer on Kibbud Av V'Em that Kibbud Av V'em trumps middas chasidus. It does not trump an explicit issur, but will override chumros a person typically keeps.

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