A Time to Tear and a Time to Mend: Reimagining Teshuva in Light of Rabbinic Narratives

On Rosh Hashanah it is inscribed, and on Yom Kippur it is sealed - how many shall pass away and how many shall be born, who shall live and who shall die, who in good time, and who by an untimely death, who by water and who by fire, who by sword and who by wild beast, who by famine and who by thirst, who by earthquake and who by plague, who by strangulation and who by lapidation, who shall have rest and who wander, who shall be at peace and who pursued, who shall be serene and who tormented, who shall become impoverished and who wealthy, who shall be debased, and who exalted. But repentance, prayer and righteousness avert the severity of the decree.

(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.

...For those of which we are aware, we have already declared before You and confessed them unto You; and for those of which we are not aware, before You they are revealed and known, as it is said, “The hidden things belong to Adonoy, our God, but the revealed things are for us and for our children forever, that we might fulfill all the words of this Torah.”⁴⁹Devorim 29:28. For You are the Pardoner of Yisrael, and the Forgiver of the tribes of Yeshurun in every generation, and beside You, we have no King Who forgives and pardons—only You! God, before I was formed, I was unworthy [to be created]. And now that I have been formed, it is as if I had not been formed. I am like dust while I live, how much more so when I am dead. Here I am before You like a vessel filled with shame. May it be Your will, Adonoy, my God, and the God of my fathers, that I shall sin no more, and the sins I have committed before You, cleanse them in Your abundant mercies; but not through suffering and severe illness. My God, guard my tongue from evil and my lips from speaking deceitfully. To those who curse me, may my soul be unresponsive; and let my soul be like dust to all.

(4) Among the ways of repentance are, for the penitent to continue to cry out in tearful supplication before the Name, to bestow alms according to his means, and to distance himself exceedingly from the thing wherein he sinned, to have his indentity changed, as if saying: "I am now another person, and not that person who perpetrated those misdeeds", to completely change his conduct for the good and straight path, and to exile himself from his place of residence, for exile atones iniquity, because it leads him to submissiveness and to be meek and humble-spirited.⁴Rosh-ha-Shanah, 16b. C.

...another explanation: Become dirty in the dust of their feet: This refers to Rabbi Eliezer; And drink in their words thirstily: This refers to Rabbi Akiva.
What were the origins of Rabbi Akiva? They say that he was forty years old and had still not learned anything. Once, he was standing at the mouth of a well and he said: Who carved a hole in this stone? They said to him: It is from the water, which constantly [falls] on it, day after day. And they said: Akiva, don't you know this from the verse (Job 14:19), “Water erodes stones”? Rabbi Akiva immediately applied this, all the more so, to himself. He said: If something soft can carve something hard, then all the more so, the words of Torah, which are like steel, can engrave themselves on my heart, which is but flesh and blood. He immediately went to start studying Torah. He went with his son and they sat down by the schoolteachers. He said to one: Rabbi, teach me Torah! He then took hold of one end of the tablet, and his son took hold of the other end. The teacher wrote down aleph and beit for him, and he learned them (aleph to tav, and he learned them; the book of Leviticus, and he learned it). And he went on studying until he learned the whole Torah. Then he went and sat before Rabbi Eliezer and Rabbi Joshua. My masters, he said, open up the sense of the Mishnah to me...

There was an incident involving a certain man who was diligent about the mitzva of ritual fringes. This man heard that there was a prostitute in one of the cities overseas who took four hundred gold coins as her payment. He sent her four hundred gold coins and fixed a time to meet with her. When his time came, he came and sat at the entrance to her house. The maidservant of that prostitute entered and said to her: That man who sent you four hundred gold coins came and sat at the entrance. She said: Let him enter. He entered. She arranged seven beds for him, six of silver and one of gold. Between each and every one of them there was a ladder made of silver, and the top bed was the one that was made of gold. She went up and sat naked on the top bed, and he too went up in order to sit naked facing her. In the meantime, his four ritual fringes came and slapped him on his face. He dropped down and sat himself on the ground, and she also dropped down and sat on the ground. She said to him: I take an oath by the gappa of Rome that I will not allow you to go until you tell me what defect you saw in me. He said to her: I take an oath by the Temple service that I never saw a woman as beautiful as you. But there is one mitzva that the Lord, our God, commanded us, and its name is ritual fringes, and in the passage where it is commanded, it is written twice: “I am the Lord your God” (Numbers 15:41). The doubling of this phrase indicates: I am the one who will punish those who transgress My mitzvot, and I am the one who will reward those who fulfill them. Now, said the man, the four sets of ritual fringes appeared to me as if they were four witnesses who will testify against me. She said to him: I will not allow you to go until you tell me: What is your name, and what is the name of your city, and what is the name of your teacher, and what is the name of the study hall in which you studied Torah? He wrote the information and placed it in her hand. She arose and divided all of her property, giving one-third as a bribe to the government, one-third to the poor, and she took one-third with her in her possession, in addition to those beds of gold and silver. She came to the study hall of Rabbi Ḥiyya and said to him: My teacher, instruct your students concerning me and have them make me a convert. Rabbi Ḥiyya said to her: My daughter, perhaps you set your sights on one of the students and that is why you want to convert? She took the note the student had given her from her hand and gave it to Rabbi Ḥiyya. He said to her: Go take possession of your purchase. Those beds that she had arranged for him in a prohibited fashion, she now arranged for him in a permitted fashion. The Gemara completes its point about the reward of mitzvot and points out how this story illustrates the concept: This is the reward given to him in this world, and with regard to the World-to-Come, I do not know how much reward he will be given.