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As we know, regret is part of teshuvah. However, sometimes even though we understand logically that what we've done is wrong, we may not always sincerely regret it. In such case, two questions arise:

  1. Is teshuvah invalid if my regret is not sincere ( i.e. I understand what I've done is a sin but I just can't make myself sincerely regret it)?

  2. Is there a way to make oneself sincerely regret a sin (realize the severity of the sin, etc)?

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    1. THere's no measure of sincerity, I suspect the Tshuvah is not accepted only of one is truly insincere, but if one has the slightest honesty in his repentance he's fulfilled the Mitzvah. BTW the original Mitzvah is to say the Viduy, not to Do Teshuva. 2. IMHO the simplest way of regretting is fearing the punishment (like one regrets when pays a fine). – Al Berko Sep 13 at 9:21
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    It might be helpful to remember the feeling that we have when the police car appears in our rear view mirror with lights flashing and we have been speeding. – Avrohom Yitzchok Sep 13 at 10:44
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Great question!

Regarding 1 - There is a rule (will add source, later - there are a few) that if one says "I will sin and do teshuva then sin again", the teshuva is ineffective. So, at the least, prior to doing to teshuva, one needs to realize the severity of the sin sufficiently to the point that he resolves not to repeat it. To me, that seems like he definition of "regret".

Regarding 2 - There is no single clear way to do this. Each person's emotions, behavior and thinking is different. One way that I have heard from numerous people is this:

One must imagine God as a benevolent father. (Not so ridiculous esp. when the term Avinu Malkeinu is used so much during the High Holidays!) Your father would do anything whatsoever for you and expects the best behavior from you and loyalty to him in return. If God is your father, and you have sinned, essentially, you have been disloyal to him and disappointed him. You haven't lived up to his standards and his standards for you are placed in a way that is designed to benefit you and improve your life. It's for you; not for him. Wouldn't you think to yourself, "How can I disappoint my father who has been so good and generous to me?"

Such is your relationship with God.

Perhaps, this helps.

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    Thanks, this helps) – Dan Weisberg Sep 13 at 10:55
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    Good. I think the explanation sounds simple. It's not necessarily easy to implement it, though, I must admit. As a kid, I saw my own father far more often than I "saw" God. – DanF Sep 13 at 15:25

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