Our Gemara on Amud Aleph discusses a scenario where someone swore falsely and denied possession of an object.  If he confesses and wishes to repent, part of his responsibility is to return the principal object as well as one fifth additional payment.  This requirement is so extensive, that even if the victim moved to far flung regions, the strict letter of the law requires that he incur the trouble and the expense to restore the object to its rightful owner.  Notwithstanding this, should the owner forgive the debt, he is off the hook.  What if he he forgives all, excepting less than a peruta value?  In such a case, the Gemara discusses the strict law, that he no longer has to return it, but also secondary concerns such as if the object is still extant, it may increase in value to the point that it now is worth more than a peruta. Because of that concern, he should return it anyway.

Regardless of the legal technicalities, we might wonder what is the backstory to such behavior. Why would anyone forgive everything EXCEPT for less than a peruta???  There is a general difficulty that newbies to Gemara have, which is they tend to ask about seemingly far-fetched scenarios in the Gemara, “But, why?”  The Yiddish answer is, קשיא אויף א מעשה! “We don’t ask questions about a story”, meaning to say, “Nu, strange things happen in real life.”  Sometimes the Gemara constructs a far-fetched scenario to bring out a deeper distinction or principle that is operative in the law. Exceptions often teach us the rule. 

However, in this case, the behavior is suggestive of a particular motive.  The victim seems to be making a statement, “I am not petty and will forgive the money, but I am holding back on a small amount symbolically to a show that I do not yet feel fully appeased.” It is a bid for the perpetrator to make a sincere appeal and apology beyond restitution.

Is it ethical to keep someone wiggling on the hook? Rama (Shulchan Aruch 606:1) rules that ordinarily it is considered cruel to hold back forgiveness. However, if there is a genuine belief that this will “teach him a lesson”, then it is permitted.  This may explain Yosef’s seemingly vindictive behavior to his brothers, putting them through intense psychological torture, as described vividly in Bereishis (chapters 42-44). He may have felt that the conflict and rivalry in the family would continue and hurt everyone unless he knows they have achieved true regret. After all, he now was the ruler of Egypt, and no longer the week younger brother. If the Shevatim declared war, it would not be pretty. Midrashim hint at tuus dynamic (Rashi Bereishis 44:18 and Bereishis Rabbah 93:6.) 

Interpersonally, true regret often comes from empathizing and deeply understanding the impact of the behavior on others. Indeed, in a key verse (ibid 42:21), the brothers are humbled by being forced to contemplate their father’s pain if they come back with yet another missing sibling. They must forces them to come to terms with how much pain they caused their father at the loss of Yosef:

וַיֹּאמְר֞וּ אִ֣ישׁ אֶל־אָחִ֗יו אֲבָל֮ אֲשֵׁמִ֣ים ׀ אֲנַ֘חְנוּ֮ עַל־אָחִ֒ינוּ֒ אֲשֶׁ֨ר רָאִ֜ינוּ צָרַ֥ת נַפְשׁ֛וֹ בְּהִתְחַֽנְנ֥וֹ אֵלֵ֖ינוּ וְלֹ֣א שָׁמָ֑עְנוּ עַל־כֵּן֙ בָּ֣אָה אֵלֵ֔ינוּ הַצָּרָ֖ה הַזֹּֽאת׃

They said to one another, “Alas, we are being punished on account of our brother, because we looked on at his anguish, yet paid no heed as he pleaded with us. That is why this distress has come upon us.”

Holding back forgiveness to help a person realize the full gravity of his actions is considered morally proper, and sometimes necessary in relationships with repeated betrayals and failures to be trustworthy. However, we must be careful to analyze our motives as well as weigh the ability of the other person to internalize this difficult message and rebuke.