How can my prayers of repentance be effective?

With regard to repeated sins: at any time, a person can sincerely repent for a past sin, which may have been committed multiple times, and resolve not to repeat it again in the future.

Moses descending from Mount Sinai with the Second Tablets on Yom Kippur

When the person repents, if he feels true remorse, shame and bitterness in his heart because of the sin that was committed, and he is repulsed by the thought of ever committing that sin again, then surely that is a sincere repentance that will be accepted by G-d. However, if at some later time the person encounters that temptation again, he may face the same struggle with his evil inclination all over again. Hopefully, with the strength gained from his previous repentance and his increased understanding of the importance of not sinning, he will be able to overcome the challenge.

Setbacks and challenges

However, if he weakens and succumbs to his evil inclination (which is crafty and knows the best way to trick or entice the person), he must as soon as possible come back to his senses and sincerely repent for the repeated sin. For sins between a person and G-d, one shouldn’t think that he won’t be forgiven again. G-d’s attributes are infinite, including His attribute of forgiveness for one who is sincerely penitent. A cornerstone of trust in G-d is that He always accepts sincere repentance. But the goal is that from the outset, one should not sin.

A resource with important details is the chapter on “Repentance” in The Divine Code by Rabbi Moshe Weiner.[1] An important point is that if someone sins against another person, through damaging or harming, either physically, emotionally or financially, his repentance isn’t complete until he makes restitution to the victim (for example, for theft, by returning what he stole) and asks for forgiveness, and the victim is appeased and forgives him. If a situation arises in which that is not possible (for example, if the victim is unknown or passed away, or unwilling to forgive), the advice to follow is included in the above chapter and in the Seventh Gate of the book Seven Gates of Righteous Knowledge.[2]

Another important point is that during the normal course of his daily routine, one must not fall into the mistake of dwelling on his bitterness and remorse over sins, because that is a trick of the evil inclination to bring a person to fall spiritually and begin to sin. One must always remember the obligation to “serve G-d with happiness” (Psalm 100), and this applies during all your daily activities, since you must “know G-d in all your ways.”

Choosing a time to pray for forgiveness

Therefore, special and limited times should be set aside, in quiet privacy, for one to turn his thoughts to his past sin and allow himself to concentrate on his remorse and bitterness, and confess the sin to G-d and plead for forgiveness. The best time for this is at night, in one’s prayers before going to bed. Once this has been achieved, one should experience relief and thankfulness to G-d, and go on to serve G-d happily. One should especially thoroughly understand and take to heart Psalm 51, and it is strongly suggested to recite this Psalm after one’s prayers of repentance in the evening.

Although Gentiles should not observe Yom Kippur (which is based on the relationship between the Jews and G-d), they should also not make the mistake of thinking that they are lacking in any way in their opportunity at any time for successful repentance (which a Jew can also accomplish at any time). The fact that Yom Kippur was commanded to the Jews – corresponding to the day that Moses descended from Mount Sinai with the second Tablets of their Ten Commandments – should only be a positive influence, in that it can inspire a Gentile to do his or her own needed repentance on that day or any day of the year (with no fasting required).

For deeper spiritual insights into the concept of repentance, please read our web page about the Covenant of the Rainbow.

Footnotes:

[1] Biblical references are included there, and the practical rules that are listed on how to achieve repentance are taken primarily from the Mishneh Torah by Maimonides (Rambam), in the section on “Laws of Repentance.”

[2] Now available to read on-line.