The Targum1 renders the phrase in the portion of NitzavimG‑d will circumcise your heart,”2 to mean “the foolishness of your heart.”

The Targum does so to forestall the following question: “Circumcision” applies only to the removal of the coarseness and foolishness that covers the heart, not to the heart itself.3

Rashi, however, whose custom is to explain all difficulties in a verse’s simple context, does not comment on these words at all. Evidently, according to him the verse is self-explanatory.

How are we to understand this verse according to Rashi?

Earlier on,4 the verse states: “There shall come a time when you will experience… and you will return to G‑d your L-rd… with all your heart and soul.” The verse then goes on to say: “G‑d will circumcise your heart.” It follows, then, that the verse here cannot possibly be referring to the foolishness of the heart, for it is alluding to a time when the Jews have returned to G‑d “with all their hearts and souls.”

We must conclude that the phrase “G‑d will circumcise your heart” refers not to the removal of the barrier of foolishness, but to the attainment of an even higher level — “that you will love G‑d your L-rd, with all your heart and soul.”

Or to put it slightly differently: The verse first states that the Jewish people will repent and obey G‑d “with all their hearts and souls” — a level that can be attained even when they serve G‑d only out of fear and awe.5 Then verse then goes on to state that the Jews will “love G‑d with all their hearts and souls.”6

We must, however, understand the connection between “circumcision” — an act of removal — and the attainment of love for G‑d.

An additional question: “G‑d will circumcise your heart” refers to an action brought about by the A-mighty, while love of G‑d is a commandment incumbent upon every Jew — “You shall love G‑d, your L-rd, with all your heart, with all your soul and with all your might.”7

The answer to these questions will become clear upon closer examination of the above-mentioned verses. “There shall come a time when you will experience… and you will return to G‑d your L-rd… with all your heart and soul,” continues the earlier theme about the state of exile that results from the Jewish people’s “forsaking [of] G‑d’s covenant.”8

The Torah also explains how this sad state of affairs can come about: “You know full well that we lived in Egypt… you saw their abominations… there may be among you… [those] whose heart strays.”9

It is thus understandable that when the Torah says “G‑d will circumcise your heart” it is referring to the removal of the cause of spiritual descent — the removal of the possibility of observing their abominations, which in turn leads to a straying of the heart.

For there are two general reasons why a Jew’s heart might stray from G‑d:

a) a fault in the heart itself — a coarse or foolish heart;

b) a fault outside the heart — “the eye sees and the heart desires.”10 In the latter situation, even if the heart itself would not normally indulge in sin, that which the eye sees gives birth to a desire within the heart.

The verse is here referring not to a case where the heart itself is “coarse” or “foolish,” but to this latter situation, where “observing their abominations” might lead to the heart’s straying.

The reason why the term “circumcise” is used now becomes clear: It is necessary to “circumcise” and cut off the connection between that which is observed and the heart, so that the heart will not desire that which the eye sees.

It is also understood why this requires an act of G‑d — “G‑d will circumcise.” Man can only remove the folly and coarseness of his heart; the connection between the eye’s seeing and the heart’s desiring is something intrinsic to man’s nature. Only G‑d can negate this.11

Based on Likkutei Sichos, Vol. XXIX, pp. 167-170