1)

What is the significance of "Beni Im Chacham Libecha Yismach Libi Gam Ani"?

1.

Shabbos 14b: When Shlomo decreed Eiruvin and Netilas Yadayim, a Bas Kol (voice from Shamayim) said this verse.

2.

Malbim: This is the Musar that one should tell his son. Chacham Lev is one that the laws of Chachmah are fixed in his heart - the power that rules over all his powers - to the point that they do not raise images of desire. The war in his Ru'ach is silenced. If you reached this level, also I will rejoice. It already said "Ben Chacham Yismach Av" (10:1), but that is not Simchas Lev - a complete inner Simchah, for he can still falter from Chukei ha'Chachmah. If his heart is Chacham, his heart rejoices in his toil, for he does not have any more war. Also his father's heart rejoices.

2)

Why does it say "Gam Ani"?

1.

R. Yonah: Just like you rejoice in your Chachmah - "Pekudei Hashem Yesharim Mesamchei Lev" (Tehilim 19:9), also my heart will rejoice.

2.

Ma'alos ha'Torah (DH Davar Acher): "Yismach Libi" is his earthly father. "Gam Ani" is his Father in Shamayim.

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