Articles
Teshuvah: Asking Forgiveness
September 26, 2025

Rav Avrohom Aba Freundlich
Rosh Bais Horaah, Lakewood, NJ 
Halachah: When one is asked forgiveness, he shouldn’t be an achzari and difficult to forgive.
Q Reuven is asking forgiveness from Shimon. Shimon feels that although Reuven is asking sincerely, he hasn’t stopped to think of all the ramifications that resulted from what he did and how much Shimon was hurt. Should Shimon forgive him?
A Yes.
Q If the offended person feels that the offender said nothing to pacify him for the wrong done to him and the whole asking forgiveness is just lip service. Should he forgive the person?
A He doesn’t have to.
Q Is it meritorious to forgive in this case?
A Yes.
Q If a gentile asks mechilah, must one also grant mechilah?
A Yes.
Q Reuven hurt Shimon and is asking mechilah. Shimon knows that the right thing is to be mochel, but he still feels some hurt. May Shimon refuse the request to Reuven’s face but in his heart still be mochel him 100 percent? Is forgiving him in his heart enough to fulfill the halachah of not being an achzari?
A No, he must tell Reuven that he’s mochel him.
Q Reuven wronged Shimon but didn’t see him until a few months after Yom Kippur, when he then asked for forgiveness. Shimon answered that in truth he hurt him very much, but at Kol Nidrei they made an announcement in shul that everyone should say they are mochel everyone. He went through the motions and said that he’s mochel him even though truthfully he really held it against him in his heart.
Is Reuven forgiven?
A Yes.
Q Someone was parking their car and were in doubt if they damaged another car. Technically, one is free from payment because of hamotzi meichaveiro alav haraya. That’s fine concerning a monetary commitment. What about teshuvah? Must he still ask forgiveness?
A If you sincerely feel there was a possibility, yes. You should say that you have a doubt you damaged him and ask forgiveness.
Q What if he wasn’t obligated to pay because it was a grama, must mechilah still be asked?
A Yes.
Q In the above two cases, must teshuvah still be done bein adam lamakom?
A Yes.
Q Reuven hurt Shimon and must ask mechilah, but he’s very embarrassed to tell Shimon what he did to him. May Reuven ask mechilah in a general way and just say, “If I may have hurt you in any way please be mochel me?”
A Yes, but it’s meritorious to specify the sin if possible.
Q Reuven is a therapist in anger management. He prides himself in having a student like Shimon who has completely succeeded with his therapy in removing any trace of anger. Unknown to Reuven, in a fit of rage, Shimon broke Reuven’s window. If Shimon tells Reuven what happened, Reuven will be completely broken and hurt. May Shimon ask mechilah in a general way without saying exactly what happened?
A Yes, however, he must find a way to pay for the damage.
Q When Reuven asked Shimon forgiveness, he said, “Can we forget about what happened and go further from now on like nothing happened?” Shimon answered, “I think that’s a great idea!” Neither one used the word mechilah. Is Reuven completely forgiven?
A Yes.
Q Must Reuven ask forgiveness again and specifically use the word mechilah and get Shimon to say the words, “I am mochel you”?
A It’s not necessary, and one is completely forgiven without this, however, it’s meritorious if one does this.
Q Someone was talking and wasn’t dan l’kaf zechus another individual. Must one ask mechilah each time this happens?
A If by not judging favorably someone was hurt, you must ask mechilah. If no hurt resulted, you don’t have to tell the person or ask forgiveness from him. However, there still remains a bein adam laMakom that requires teshuvah.
Q When asking mechilah one doesn’t get a kapparah unless they ask the person forgiving to daven for them. What should be said in this tefillah?
A Wishing the person hatzlachah.
Q Is this a halachah or something meritorious?
A Meritorious.
Teshuvah
The Dubno Maggid tells the story of a thief observing a very successful store. He was amazed at how many people were coming in and going out purchasing items. Realizing that there must be a tremendous cash turnover, he began planning a robbery. He observed that toward the end of each day, a man would walk with a thick attaché case to the bank, obviously with the daily profits. It wasn’t dark yet, and the streets were full of people. He couldn’t just grab the case from him. It was almost hopeless. Then he had a great idea.
Every day on the way to the bank, the man passed an expensive clothing store. The next day, a half hour before closing time, before the man left with the case, the thief went into the clothing store. He told the owner he worked for a wealthy banker who needed three suits.
“You’ve come to the right place. Tell him to come in and we’d be happy to fit him!”
“That’s the problem!” replied the thief, “He’s just too busy. He asked me to bring him some samples, and he’d leave a deposit.”
“Well what size is he?” said the owner.
“Umm, I don’t know, but I have an idea! When I see someone in the street around the same size as my boss, maybe you can ask him to come in and try on some suits for size?”
“Great idea!” replied the owner.
They waited. As the man with the attaché case was walking by, “that’s him!” the thief said. “He’s the same size!” The owner quickly ran to the man and asked, “Would you mind trying on some expensive suits for size for someone in my clothing store across the street?”
“Expensive suits, why not?” thought the man as he followed him into the store.
He tried on the suit and wedged the valuable case securely in between his legs. As the owner made notes of the exact size, the thief grabbed the case and ran. The man started to chase the thief, but the owner grabbed him. “One minute, you can’t go anywhere before you take off the suit!”
“But he’ll get away,” cried the man.
“You must take my suit off before you go anywhere!”
The Dubno Maggid explains that the thief is the yetzer hara. His entire goal and purpose is to steal all our money, the s’char mitzvah we earned. How does he do it? Just try on this expensive suit! You’re just trying it on for size! You’ll enjoy wearing it, even just for a short time! Just try the worldly pleasures—not made for you—just try it for a few minutes! You’ll enjoy it! Oy! Just as we begin to enjoy the feeling, the yetzer hara runs away with all our money! We can’t even chase him. We have to take the suit off first—that’s to do teshuvah! [1]
Wouldn’t it be wonderful if a friend would be near us before we try on the suit, and warn us, “Be careful, there’s a thief near you!” That friend is Elul and blowing the shofar on Rosh Hashanah. Hashem, with His infinite kindness, has given us the refuah before the makkah. Elul and shofar to awaken us to teshuvah before the sealing the din on Yom Kippur.[2]
Perhaps the beginning of the teshuvah process should be to be makir mekomo, to realize who we really are. If we truly understand that, we never would try on a thousand dollar suit to begin with.
[1]ספר אוהל יעקב בלק לא הביט און ביעקב כג, כא, בד”ה אבל עוד נראה
[2]ספר שערי ארמון,הרב שלום מאיר ולך, עמוד 7