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Why does Rabbeinu Yonah reverse the normal order of teshuvah for habitual sins, requiring one to first commit to stopping before expressing regret? For ongoing transgressions, genuine regret is impossible while maintaining intent to continue sinning. The shiur applies this principle to interpersonal offenses, showing how even forgiven wrongs may still require teshuvah to God.
This shiur delves into a fundamental principle from Rabbeinu Yonah regarding the proper order of repentance (teshuvah). The core teaching distinguishes between two types of transgressions: occasional sins versus habitual ones. For sins committed occasionally or accidentally, one follows the standard order of repentance - first expressing regret (charatah) over past actions, then accepting upon oneself not to repeat them in the future (kabbalah l'atid). However, for sins done habitually or with ongoing intent, Rabbeinu Yonah teaches that one must first uproot the future desire before dealing with past regret. Rabbi Zweig offers multiple explanations for this counterintuitive teaching. The first explanation focuses on the nature of the problem: when someone commits habitual sins, their primary issue is the present desire to continue sinning. Since the current desire represents an active problem while past actions are merely history, one must first address the pressing issue of future intent.
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Rabbeinu Yonah on repentance
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Why does Rabbeinu Yonah require da'agah (worry) as a separate principle of teshuvah beyond regret? The shiur develops that the heart and eyes act as 'sarsur aveirah' - not mere conduits but active intermediaries that influence sin. Each requires its own repair: the heart through brokenness, the eyes through tears that serve as 'dam ayin' - a sacrifice from the sinning organ itself.
