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One who says, ‘I will sin, then repent; I will sin, then repent’ is not permitted to repent. (Masechet Yoma 85b)

What happens to somebody who says to himself, "I will sin then repent, sin then repent," then does exactly so numerous times in a wicked way.

However, later on he realizes that this was his biggest mistake in life and - thinking he lost his chance of doing teshuvah - feels true genuine regret, begins to live an honest and upright life, is humble to himself and the people around him/her, changes his wicked ways once and for all, tries to repent with full love for Hashem, tries to do teshuvah in all honesty as effectively as possible with full heart, soul and intention, doesn't want to lose the ability to do teshuvah, feels remorse and never returns to the sin again.

Can Hashem have mercy on that soul?

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    Insofar as saying "I will sin and repent" is itself a broad sin, it stands to reason that one can repent from exactly that. Kind of meta, when you think about it.
    – Yehuda
    Nov 9, 2023 at 14:25
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    I heard a chassidic take on this. The kabbalistic inyan of teshuva is that it is a method of redeeming a spark from the klipa of the aveira. If one does an aveira with the intention of doing teshuva, one hasn't properly sinned. It's a half-hearted sin at best, certainly not sinning "lishma".
    – Rabbi Kaii
    Nov 15, 2023 at 16:38

3 Answers 3

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Refer to the Mishnah in Yoma 8:

With regard to one who says: I will sin and then I will repent, I will sin and I will repent, Heaven does not provide him the opportunity to repent, and he will remain a sinner all his days.

The Rosh explains this gemara to mean that the teshuvah-process is more difficult. It does not mean we aren't given the opportunity to do teshuvah, but it is more difficult to do so (plus, no heavenly assistance). Refer to here.

However, we don’t know what G-ds plans are.

The Bartenura on that Mishnah explains it. He says that because a person sinned so much, he thinks it became permitted from him, so he does not see the problem.

Maybe the solution for this, is to break that thought. The Gemara in Eruvin says that the yetzer hara is like a spidersweb. If you fly in it, you might could get out of it, but if you keep moving towards it, you will get stuck in it. So too with the yetzer hara.

The description you give at the end of your question is exactly what Rambam defines as Teshuvah. If you really will work on yourself, and if you are willing to abandon sinning, that constitutes teshuvah.

And remember, G-d is merciful!

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    Does not provide him an opportunity to teshuva does not mean he does not have the ability to do teshuva only that he isn't given assistance and the teshuva must come from the person himself
    – Dude
    Nov 9, 2023 at 15:47
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    That is exactly what it says and how I read it :)
    – Shmuel
    Nov 9, 2023 at 17:41
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    @Igal Heim does this answer your question?
    – Shmuel
    Nov 17, 2023 at 16:04
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    I agree. It does. G-d is merciful :)
    – user33852
    Nov 26, 2023 at 15:23
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Rambam, Hilchot Teshuvah, Chapter 4:

1. There are 24 deeds which hold back Teshuvah: Four are the commission of severe sins. God will not grant the person who commits such deeds to repent because of the gravity of his transgressions.

They are:

...

d) One who says: "I will sin and then, repent." Included in this category is one who says: "I will sin and Yom Kippur will atone [for me]."

...

6. All of the above, and other similar transgressions, though they hold back repentance, they do not prevent it entirely. Should one of these people repent, he is a Baal-Teshuvah and has a portion in the world to come.

(Touger translation, my emphases)

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Tanya, Iggeres HaTeshuva 11:

ואין זה ״אחטא ואשוב״, כי היינו דוקא שבשעת החטא היה יכול לכבוש יצרו, אלא שסומך בלבו על התשובה, ולכן, הואיל והתשובה גורמת לו לחטוא – ״אין מספיקין וכו׳״. ואף גם זאת ״אין מספיקין״ דייקא, אבל אם דחק ונתחזק ונתגבר על יצרו ועשה תשובה – מקבלין תשובתו.

But [requesting pardon thrice daily] is not an attitude of “I will sin and later repent.” That is relevant only if while committing the sin he could have overcome his impulse to evil, but depended in his heart on repenting later. Since the opportunity to repent caused him to sin, “He is not granted an opportunity….” And even then, he is not granted an opportunity. But if he pressed forcefully and overpowered his evil impulse and did repent, then his repentance is accepted.

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