How to Repent from Sins We Enjoyed

The Aish Rabbi Replies

Thank you for raising the profound issue. The simple answer is that regret doesn't mean we must pretend we didn't enjoy our sin in the first place. It means that we regret that we disobeyed God. You are right that very often we cannot deny that our sin gave us pleasure - which is of course why we sinned in the first place.

This actually touches on an important general issue regarding our attitude towards sin. The Midrash (Torat Kohanim 9:12) says that we should not say non-kosher and other sinful activities are repulsive to us. We should rather say that we would love to do such behaviors, but what can we do because God forbade it. Here as well, we are not expected to honestly say the non-kosher we ate did not taste good, just that we wish we had listened to God and passed up on that pleasure.

The above must be qualified with an important distinction made by Maimonides (Shemoneh Perakim Ch. 6). The attitude advised by the Midrash – that we should say we’d love to sin except that God forbade it – is limited to “irrational” commandments – ones which make no logical sense to us, such as refraining from eating pork or shaving our sideburns. Those we only refrain from doing because God said so. Regarding rational mitzvos, however, such as not killing or stealing, we should develop ourselves spiritually to appreciate that such actions are inherently wrong and unethical ways to behave. Thus, if a person sinned by publicly shaming his fellow, his “repentance” must not be: “I’m really glad I gave it to him, but I wish I hadn’t accrued a sin.” Rather, our repentance must include a heightened realization of how cruel it is to embarrass another human being. See this past response regarding this general topic.

At the same time, in a sense, when it comes to repentance (teshuva), there is a much higher ideal we must strive for. People sometimes mistakenly view teshuva with an attitude something like this: “Those were the good old days when we used to live it up. But nebach (alas), now we know better and must behave!” It’s quite obvious that such “repentance”, even for illogical prohibitions, is sorely lacking. Teshuva means dissociating ourselves from our past sins: wishing we had never done them and created a distance between ourselves and our Creator. Rather than fondly reminiscing about the old days, we should cringe at our past memories of disobeying our beloved Father. Even though we did enjoy the pleasure, our minds should associate such past experiences with the painful recollection of how distant we used to be from God and how deeply our actions disappointed Him. And with our entire hearts, we wish they had never occurred.

(Obviously, such feelings will be much less pronounced if we did not know better at the time we used to sin. Yet even so, we should not be longing for the days when we had no idea of the significance of our actions. Our sinful, even ignorant, past is simply not who we are today. And we could not be happier that our past behavior is now long behind us.)

See also this article I wrote on another website about this topic.