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How can we authentically promise on Yom Kippur never to sin again without being delusional? The Rambam (רמב"ם)'s definition of a baal teshuvah reveals that true repentance isn't about controlling future temptations, but about severing the psychological connection between past sins and present decisions. We're not promising never to sin again, but ensuring that if we do sin, it won't be because we sinned before.
This shiur addresses a fundamental challenge of Yom Kippur: How can one authentically commit to never sinning again without being delusional or insincere? Rabbi Zweig begins by acknowledging the discomfort many feel when making promises they suspect they cannot keep, noting that either we're deluding ourselves or being insincere - both problematic approaches to this holy day. The core insight comes from analyzing Maimonides' definition of a baal teshuvah (penitent person). The Talmud (תלמוד), codified by Maimonides, states that true repentance occurs when a person finds themselves in the exact same circumstances as their original sin - same place, same person, same desire and energy - yet chooses not to transgress. Rabbi Zweig asks a penetrating question: why must it be the exact same circumstances? Wouldn't resisting the same type of sin with equal temptation be sufficient?
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