Would any sources seem to indicate that if one states when talking to Hashem “HaShem if I ever regret any of my mitzvot, I don’t really regret them.” then any regrets he would have in the future would not take away the reward for his mitzvot?

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    It sounds similar to saying in the morning all the attributes of hashem and then saying that they should apply each time I mention his name although I dont know or think of them at the time. – interested Aug 31 at 12:30
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    Up for the easy way, aren't we? ;) – Ilja Aug 31 at 12:57
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    How is this different from saying, "Hashem, if I ever think forbidden thoughts, I'm not really thinking them" and thus any sinful thinking he would have in the future wouldn't count? If there is a reason to differentiate, the question would be strengthened by incorporating it. – Jay Aug 31 at 15:47
  • This is like saying to HaShem that if one ever prays to idols they don't really mean it. Or if one ever commits a sin it was an accident, etc, etc. – Turk Hill Aug 31 at 23:04
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    @Daniel I have no sources to offer just a personal opinion. I would be inclined to say it would not work. The mechanics don't add up in my eyes. Let's make a timeline. Monday he stipulates regrets shouldn't work. Tuesday he does the mitzvah. Wednesday he regrets the mitzvah. Wouldn't he also regret the stipulation? Would we ever say he can regret away a mitzvah but not a stipulation? And what happens if someone regrets having regretted? Does his schar mitzvah come back? I'm not sure how far we can extend this idea of regret before we exit the realms of logic. – user6591 Sep 2 at 3:32

The question reminds me of “Kol Nidrei”.

In KN, the request is to annul vows. These, say Wikipedia

are almost exclusively religious pledges of various kinds: That something will be done (or not done) or given in exchange for a prayer being answered, that something will be done (or not done) for religious purposes or to show religious devotion, that a thing will be used only for religious purposes (e.g., as a tool used only for building or repairing the Temple) and never for mundane purposes, that a thing will be given to the Temple or treated as if it were already given to the Temple, and so forth.

The Kol Nidrei declaration can invalidate only vows that one undertakes on his own volition. The invalidation of future vows takes effect only if someone makes the vow without having in mind his previous Kol Nidrei declaration. But if he makes the vow with Kol Nidrei in mind—thus being openly insincere in his vow—the vow is in full force.

So it is possible to nullify in advance promises to do something good. The question wants to nullify in advance a promise to do something bad (regret doing a mitzvah).

I could suggest that as we know that the deep-down intention of a Jew is to do good things (example from forcing a man to bring a korban, see here) a bad thought is essentially not what he desires and therefore it should be possible to annul it in advance.

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    We also have hataras nedarim every year, so we don't rely on kol nidrei. We don't assume that it works for the future. – Jay Sep 2 at 19:05

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