The gemarah in Avodah Zara 17 relates that Rabbe Eliezer Ben Durdaya did not leave over one harlot in the world without cohabitation with her. Once he heard that there was one particular harlot in one of the overseas cities who would take a purse of dinar coins for her fee. Thereupon he took a purse of dinar coins and went and crossed seven rivers along the way for her sake. Later at the moment of the onset of cohabitation, the harlot blew with her mouth and said to Elazar just as this current of air cannot return to its place of origin so too they will not receive Elazar in repentance. Thereupon Elazer was moved to teshuvah and he repented. He placed his head between his knees and burst forth in crying until his neshama departed his body a heavenly voice then issued forth and proclaimed Rebbi Elazar Ben Durdeyah has now been readied for the life of the world to come.
What exactly was the message that this harlot was sending to Elazar that stirred him so to immediately forfeit his long journey and give up the pleasure he was insanely addicted to? This story becomes even increasingly difficult to understand if her intention with these words was to ensure to deter from Elazar any second thoughts of turning back from sinning with her. She removed all guilt from him by relating that his addiction to these immoral acts had already severed his relationship with Hashem and he can never return anyway. At least one can enjoy this world if he lost the Next World already. If this was the message she sent him what could have possibly change his mind and heart suddenly to run away from this enormous temptation he was seconds away from fulfilling?
Rav Yaakov Charlop ztl gives a fascinating interpretation to this story in order to answer these questions. This harlot herself was addicted to immoral conduct. In order to do teshuvah she ran away to a place far away from people making the journey to visit her dangerous, super costly and very time consuming. All of this was safeguards in the hope that she would not be tempted again to sin. Anybody would have to be insane in order to seek her out. When Elazar came to her, the sole intention of this Baalas Teshuvah was to persuade him not to sin with her but rather to do teshuvah. How did she achieve this goal by remarking just as this air can never return into my mouth so too you can never return these actions as if it did not happen?
Rav Charlop explains. The method through which the yetzer hara seduces one to sin is twofold: one by not allowing the sinner to think about the severity of the aveirah and its destructive power to oneself and to the world, and secondly by giving to the sinner a distorted interpretation and a false sense of security of how easy it is to do teshuvah and rectify this wrongdoing even if it involves aveiros that have become second nature.
The sinner hears this Chazal from his yetzer harah that if a sinner repents from fear, then his intentional sins become deemed as non - intentional ones. If a sinner does teshuvah from love of Hashem his intentional sins are transformed into mitzvos. It sounds like magic but unfortunately it is not so. The punishment for aveiros will forever remain because punishment from Hashem is not revenge but rather tikkun of the nefesh. When one sins there is a natural malfunction and blemish in the nefesh and that has to be fixed and repaired in order to be a vessel to receive the reward in the Next World for the mitzvos one fulfilled. If he does teshuva from fear alone, his cleansing and fixing process of his nefesh through pain and suffering will be worth it for him, for he realizes the great rewards he will get in the Next world which will outweigh the pain for his aveiros. However he will still have to undergo pain for his tikkun. When Chazal say that if he will do teshuvah from love then his aveiros become like mitzvos This concept means to convey that he will not feel pain with the repair coming from his punishment because the lights of Olam Habah are shining through its gates and he feels no pain. For when one is able to see the incredible pleasures that are awaiting him then every degree of pain becomes immeasurable pleasure and well worth the suffering to get it.
According to this explanation aveiros never go away and the blemishes that they caused upon the nefesh still remain waiting for their tikkun. It only depends if one will feel the pain of the tikkun and say it is still worth it, or he will not feel the pain what so ever because the unseen pleasures of Olam Habah overwhelms the suffering.
This is the message that the Baalas Teshuvah harlot was conveying to Elazar. Don't deceive yourself into thinking that one day you will do teshuvah out of love to Hashem and your aveiros will not only disappear but also become merits. Just like this breath can never come back so too one's aveiros cannot disappear and make believe that there never was an aveirah. It is an unfortunate reality that one's nefesh cannot escape tikkun no matter what kind of teshuvah you are going to do., whether out of fear or love.
Koheles wrote ראיתי צדיק אבד בצדקו this can be referring to אלעזר בן דורדיא from the moment he became a tzadik he died. This is hinted in the word אבד which is the acronym of אלעזר בן דורדיא.
Rav Charlop continues to explain the Medrash of Adam Harishon meeting with Kayin and Kayin tells Adam that he made a compromise with Hashem with his punishment. Upon hearing this news Adam started to sing Mizmor Shir Leyom Hashabas. What is this compromise that Kayin was revealing to Adam of which he was unaware of until the present? Adam understood the severity of his aveirah of eating from the Aitz Hadaas. He accepted the future pain and suffering. Kayin told him of a compromise in the punishment and that is with the power of teshuvah one can sweeten the punishment even though he cannot get rid of it completely. If one merits teshuva out of love, he will be granted the ability to look into the future to the reward he will receive in Olam Habah and thereby be removed from the pain and agony of the tikkun. Adam immediately began to sing and to focus on Olam Habah which the Shabbos is מעין .
On Rosh Hashana we dip apples and challah in honey. שנה טובה ומתוקה. What does the word מתוקה add on more than טובה? According to the above we can say that this minhag is making us aware that starting from Rosh Hashanah the first day of Aseres Yemai Teshuvah we must realize that we should not rely on the misconception that teshuvah removes completely any punishment coming to us because we did teshuva. Or more so let us wait to do teshuvah on Succos which is a designated time for teshuvah out of love as the sefarim tell us. We must come to realize that every aveirah has an unescapable tikkun waiting for us. Teshuvah can only sweeten the tikkun it cannot magically remove it. Teshuva from yirah can be compared to artificial sweeteners such as Saccharin which leave a bitter aftertaste. Teshuvah from love is like honey, sweet from beginning to the very end.
We must strive to do teshuvah and at least make a פשרה for our דין like Kayin and Adam Harishon did. This is the call of the שופר of Rosh Hashanah, the call for teshuvah. The gematriah of שופר is the same as פשרה with the word. The shofar represents אהבה ואחדות as the Tiferes Shlomo writes of Rosh Hashanah
עיקר ההכנה על יום ר"ה הוא להיות בין בנ"י אהבה וריעות. וז"פ (תהלים צח, ו) בחצוצרות וקול שופר הריעו לפני המלך ד'. פי' כאשר יהי' לכם אהבה וריעות בעת שהוא קול שופר אז תהיו לפני המלך ד'. פי' לפני ולפנים במקום שאין בו מגע נכר
It is also written Amos 3,6 אם יתקע שופר בעיר והעם לא יחרדו that shofar also represents יראה the call for teshuva from fear. Both teshuvah from fear and teshuvah from love cause a פשרה a compromise in the punishments that await us for our aveiros. Let us strive for the honey choice and let the gates of Olam Habah be open for us in order not to experience suffering at all for all the tikkunim we have to make אכי"ר.