How do we make Teshuvah?

§ With regard to repentance, the Gemara asks: What are the circumstances that demonstrate that one has completely repented? Rav Yehuda said: For example, the prohibited matter came to his hand a first time and a second time, and he was saved from it, thereby proving that he has completely repented. Rav Yehuda demonstrated what he meant: If one has the opportunity to sin with the same woman he sinned with previously, at the same time and the same place, and everything is aligned as it was that first time when he sinned, but this time he overcomes his inclination, it proves his repentance is complete, and he is forgiven.

§ It was taught in a baraita that Rabbi Yosei bar Yehuda says: When a person commits a transgression the first time, he is forgiven; a second time, he is forgiven; a third time, he is forgiven; but the fourth time, he is not forgiven, as it is stated: “Thus said the Lord: For three transgressions of Israel, but for four I will not reverse it” (Amos 2:6). And it says: “All these things does God do twice or three times with a man” (Job 33:29).

Furthermore: Whoever accumulates merit for the public will not have sin come to his hand, and God protects him from failing; but whoever causes the public to sin has almost no ability to repent. The Gemara explains: What is the reason that whoever accumulates merit for the public will not have sin come to his hand? It is so that he will not be in Gehenna while his students are in the Garden of Eden, as it is stated: “For You will not abandon my soul to the nether-world; neither will You suffer Your godly one to see the pit” (Psalms 16:10). On the other hand, whoever causes the public to sin has almost no ability to repent, so that he will not be in the Garden of Eden while his students are in Gehenna, as it is stated: “A man who is laden with the blood of any person shall hasten his steps to the pit; none will support him” (Proverbs 28:17). Since he oppressed others and caused them to sin, he shall have no escape.

§ The Gemara returns to interpreting the mishna. It states there that one who says: I will sin and I will repent, I will sin and I will repent, is not given the opportunity to repent.The Gemara asks: Why do I need the mishna to say twice: I will sin and I will repent, I will sin and repent? The Gemara explains that this is in accordance with that which Rav Huna said that Rav said, as Rav Huna said that Rav said: Once a person commits a transgression and repeats it, it becomes permitted to him. The Gemara is surprised at this: Can it enter your mind that it becomes permitted to him? Rather, say that it becomes to him as though it were permitted. Consequently, the sinner who repeats his sin has difficulty abandoning his sin, and the repetition of his sin is reflected in the repetition of the phrase.It is stated in the mishna that if one says: I will sin and Yom Kippur will atone for my sins, Yom Kippur does not atone for his sins. The Gemara comments: Let us say that the mishna is not in accordance with the opinion of Rabbi Yehuda HaNasi, as it was taught in a baraita that Rabbi Yehuda HaNasi says: Yom Kippur atones for all transgressions of the Torah, whether one repented or did not repent. The Gemara answers: Even if you say that the mishna is in accordance with the opinion of Rabbi Yehuda HaNasi, it is different when it is on the basis of being permitted to sin. Even Rabbi Yehuda HaNasi agrees that Yom Kippur does not atone for the transgressions one commits only because he knows that Yom Kippur will atone for them.

(1) What is complete repentance? He who once more had in it in his power to repeat a violation, but separated himself therefrom, and did not do it because of repentance, not out of fear or lack of strength. For example? One who knew a woman sinfully, and after a process of time he met her again privately, and he still loving her as theretofore, and he being in a state of potency, and the meeting is in the same land where the sin was first committed, if he parted without sinning, he has attained complete repentance. Of such Solomon said: "Remember then thy Creator in the days of thy youth" (Ecc. 12.1). Even if he made no reparation save in his old age, at a time when it was already impossible for him to repeat his misdeeds, although it is not the best repentance, it still is of help to him and he is considered a penitent. Moreover, though he continued a life of sin but did repent on his dying day, and did die a penitent, all of his sins are forgiven, even as it is said: "While the sun, or the light, or the moon, or the stars, be not darkened, nor the clouds return after the rain" (Ibid. 12.2), yea, that is the day of death. Deduct herefrom that if he remembered his Creator and did repent ere he died, he was forgiven.¹Ibid. 86b; Kiddushin, 40b; Shabbat, 151a. C.

(2) What is repentance? The sinner shall cease sinning, and remove sin from his thoughts, and wholeheartedly conclude not to revert back to it, even as it is said: "Let the wicked forsake his way" (Is. 55.7); so, too, shall he be remorseful on what was past, even as it is said: "Surely after that I was turned, I repented" (Jer. 31. 19). In addition thereto he should take to witness Him Who knoweth all secrets that forever he will not turn to repeat that sin again, according to what it is said: "Say unto Him.… neither will we call any more the work of our hands our gods" (Hos. 14.3–4). It is, moreover, essential that his confession shall be by spoken words of his lips, and all that which he concluded in his heart shall be formed in speech.²Yoma, 57b; Shabbat, 121. G.