The Rambam defines the act of teshuva [2-1]: “If one slept with a woman, and then had another opportunity to sleep with he;, if he was still attracted to her, was still in good health and was in the same location as before and desists - he has repented completely.”
What if he never met her again but desisted from sleeping with a woman far more attractive
– has he then done teshuva?! The answer is no, because teshuva is changing ones neural
pathway, mentally returning to the exact scenario and resolving never to repeat the action.
It can only ever be achieved by the reconstruction of the original scenario.
Teshuva itself is defined as letting go of the sin (3,3) and one who has not done this, but
goes through the motions of repentance is like a man going to the mikva to purify himself
with an impure object in his hand – the repentance is completely ineffective. What does
letting go mean and how does one do it?
Azivas HaChet the act of letting go of a sin is a lofty and incredibly difficult thing to do. We
think of doing teshuva as deciding for now not to do something (I’m going to keep Shabbos
this week) but fundamentally we keep the option open to us of changing our mind again.
The man in our earlier example who decides not to sleep with the woman again, but still
would love to, has not let go. Letting go is the hardest thing to do because it is declaring
that repeating that act will never have a place in our vision of reality.
We find death so shaking and disturbing because it is just so final, in contrast to any decision
we make in which we feel can be reversed should we change our minds. Letting go means
literally letting the option of sleeping with that woman die, it means that the option of going
back and performing a sin again is as impossible as speaking to the person you have just sat
shiva for. The option of repeating the sin is dead, is over and has disappeared from the
world.
The Gemara (Avodah Zara 17a) talks about a man, Elazar ben Durdia, who slept with every prostitute in the world. He once heard about a particular famous and expensive prostitute in a city overseas. Right before he cohabited with the woman, she remarked that there was no way Elazar would ever receive Teshuva if he went through with this act. Elazar was heartbroken and distraught, and immediately went outside and asked the mountains and other parts of the earth to pray for him. However, none of them would agree to intercede for him. Upon realizing that no one else would pray for him, he cried and sat in the foetal position and cried so much that he died. A heavenly voice
thereupon announced that Elazar had received a share in Olam Haba and earned the title of
Rabbi.
The reason why new years’ resolutions never last is because we are not willing to let our
previous mindset die. Rabbi Elazar ben Durdia died because sleeping with prostitutes was so
much a part of who he was that when he let the option of sleeping again with a prostitute
die, he himself died. [מפי השמועה]
