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Q&A: Scheduling Transgressions

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Originally published:
This is an English translation (via GPT-5.4). Read the original Hebrew version.

Scheduling Transgressions

Question

I’ve been struggling with sexual temptation for a long time—both wasting seed and prostitutes…. Every time I try to stop, without success.
Over the last six months I discovered that when I decide in advance when the falls will happen, I manage to hold myself back in between, both in action and in thought.
Is it permissible to “set fixed times” for a transgression, or do I need to keep fighting all the time even if in the end that means I’ll commit more transgressions overall?

Answer

I think so, yes. If that’s what helps.

Discussion on Answer

Moshe (2024-07-21)

Good for you for fighting your impulse!
Rabbi Michi’s answer fits the words of Tosafot on Chagigah 16a, who explained the statement, “Let him wrap himself in black and go to a place where he is not known and do what his heart desires,” literally—that is, it is preferable to time a transgression wisely in order to reduce its severity.

mikyab123 (2024-07-21)

It’s not exactly a match. First, the Rif and the Rosh on Moed Katan 16 wrote that the Jewish law does not follow Rabbi Ilai, since we hold that everything is in the hands of Heaven except fear of Heaven. And Maimonides and the Shulchan Arukh also did not bring his words. However, Tosafot in Chagigah does imply that this is indeed the Jewish law.
In my humble opinion, one cannot instruct this as a halakhic ruling, because a halakhic decisor cannot instruct a person to commit transgressions. And Rabbi Ilai also probably was not laying down Jewish law here, but offering some sort of recommendation for a person himself. And even regarding that, according to most halakhic decisors one should not instruct this.
Of course, one may answer an abstract Jewish-law question about the severity of each such prohibition, and that is what I answered.

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