Mishloach Manot and Strained Relationships: Law and Wisdom in Sending Mishloach Manos to an “Enemy” or Adversary
Question
There is an individual who was once my business partner many years ago. Eventually, we became embroiled in a very painful and bitter dispute, with each of us feeling deeply wronged and cheated by the other. Since then, we have completely cut off contact. The last interactions between us consisted of harsh and unpleasant messages, and we have not spoken in years. Recently, I thought that perhaps an appropriate way to initiate peace, and let bygones be bygones, would be to send him Mishloach Manos. However, a confidant of mine whom I spoke to—who is knowledgeable in Torah matters—expressed concern. He warned that this might actually worsen the situation and bring up bad memories and hurts. He also mentioned that he had heard that one should not send Mishloach Manot to someone who is a bitter adversary unless peace has already been made beforehand. Practically speaking, what is the correct course of action? What is the halachic ruling, and what would be the proper advice in such a situation?
Answer
From the standpoint of strict halacha, there is no prohibition against sending Mishloach Manos to one’s adversary or even to someone with whom one has a long-standing and painful dispute. On the contrary, such an act can potentially increase peace, goodwill, and brotherhood, and may help restore the relationship to a healthier and more positive place, which is one of the main reasons for the Mitzvah of Mishloach Manos.
That said, the poskim do discuss whether one can fulfill the mitzvah of Mishloach Manos by sending it specifically to someone with whom there is active enmity or hostility. Because of this debate, the practical recommendation is that if one chooses to send Mishloach Manot to an enemy or bitter rival, he should also send Mishloach Manot to at least one additional person, thereby fulfilling the mitzvah according to all opinions.
All of the above reflects the letter of the law. However, from the standpoint of practical wisdom and personal judgment, the situation is far more nuanced. For some people, the wounds are so deep and the anger so intense that they may refuse to accept the Mishloach Manot altogether, or the gesture may reopen old resentments and reignite hostility. Others may perceive the act as insincere or manipulative—thinking, “Not only was I wronged, but now he wants to appear friendly without ever acknowledging the harm he caused.” In that sense, there is considerable wisdom in the concern raised by your confidant. In some cases, such a gesture may indeed “rock the boat” rather than calm the waters.
Therefore, the appropriate approach is to weigh the situation carefully. If, in your honest assessment, the likelihood that this gesture will bring peace and improve relations outweighs the risk that it will provoke renewed anger or bitterness, then it is appropriate—and even praiseworthy—to do so. If, however, it seems more likely that the gesture will cause harm rather than healing, it would be wiser to refrain.
Additionally, it should be noted that reconciliation does not always begin with a symbolic or public gesture. At times, the more appropriate first step is quieter and less direct—such as allowing additional time to pass, softening one’s own heart internally, or choosing a more neutral form of communication. Mishloach Manot is a powerful expression of connection and goodwill, but precisely because of its emotional and symbolic weight, it must be used with care and sensitivity. Forcing reconciliation prematurely can sometimes hinder, rather than help, the long-term goal of genuine peace.
Explanation:
There are two primary reasons recorded for the mitzvah of Mishloach Manot. One reason of the Terumas Hadesehn is practical in nature: to ensure that everyone has sufficient food for the Purim meal (seudat Purim). By exchanging prepared foods, people are able to celebrate the day properly without embarrassment or lack.
The second reason by the Manos Levi of Rabbi Shlomo Alkabetz is relational and social—to increase peace, friendship, and unity among people. This explanation is cited by several Achronim who explains that the mitzvah is intended to foster closeness and goodwill between individuals. It is based on this second reason that a debate arises among the poskim regarding whether one can fulfill the obligation of Mishloach Manot by sending it to someone with whom he has a hostile or adversarial relationship.
One side of the debate argues that since the verse states “ish l’re’eihu”—“a man to his fellow”—this implies someone who is already considered a re’a, a friend. An individual with whom one is in an active feud does not fall under this category, and therefore sending Mishloach Manot to such a person would not fulfill the mitzvah. According to this view, the purpose of Mishloach Manot is to strengthen existing bonds of friendship, not to use Purim as an opportunity to resolve deep conflicts or to “rock the boat” by reopening unresolved disputes.
Others, however, strongly disagree. They argue that the intent of “l’re’eihu” is not to exclude those who are currently estranged, but rather to encourage the creation of friendship. According to this approach, one should specifically send Mishloach Manot to an adversary in order to transform him into a re’a and bring about peace and reconciliation. From this perspective, sending to a close friend—where peace already exists—is far less impactful than sending to someone with whom the relationship is broken. These authorities understand the mitzvah as a tool for actively increasing unity, even where it is currently lacking, and they see this as fully aligned with the intent of the Sages.
Practically speaking, since this matter remains subject to halachic debate, the proper conclusion is that one should not rely solely on sending Mishloach Manot to an adversary in order to fulfill the mitzvah. Rather, one should also send Mishloach Manot to at least one additional person who is clearly considered a friend. In this way, one fulfills the mitzvah according to all opinions, without any doubt.
It is noteworthy that some of the poskim who question the validity of sending Mishloach Manot to an adversary use this uncertainty to explain why no blessing is recited over the mitzvah of Mishloach Manot. Since it is not always clear who is truly considered one’s friend and who is considered an adversary, the Sages refrained from instituting a blessing that might be subject to doubt.
Illustrative Stories and Their Lessons
Two stories vividly demonstrate the complexity and sensitivity involved in sending Mishloach Manot in the context of deep personal hostility.
The Malbim and the Mocking Mishloach Manot: It is related that the Malbim once received Mishloach Manot from a sworn adversary who was associated with the Haskalah movement and harbored deep animosity toward him. When the Malbim removed the covering from the plate that had been sent, he discovered that it contained a sculpted image of a pig—clearly intended as a provocation and insult rather than a gesture of goodwill. The Malbim calmly removed the offensive object from the plate. He then took a portrait of himself that he had in his home, placed it neatly on the plate, and sent it back to the sender together with a note. The note read: “Thank you very much for sending me a picture of yourself. In return, I am sending you a picture of myself.” The Malbim’s response was sharp, dignified, and restrained. He neither ignored the insult nor allowed it to escalate into open conflict. At the same time, the episode highlights that when Mishloach Manot is sent without sincerity and with malicious intent, it not only fails to fulfill the spirit of the mitzvah, but can become a vehicle for mockery and harm.
The Refused Institutional Mishloach Manot
In another case, two individuals were embroiled in a long‑standing and bitter feud. One of them chose to participate in a group Mishloach Manot initiative organized by an institution, which was sent collectively to many recipients—including his adversary. When the recipient received the package and saw the list of contributors, he noticed the name of the person with whom he was in conflict. He immediately contacted the institution and stated that he refused to accept the Mishloach Manot. He protested strongly, saying that it was extremely inappropriate to send him a gift that included his adversary, and that he would not derive any benefit from something sent by someone he regarded as an enemy. He demanded that the package be taken back. In this case, the gesture not only failed to bring peace, but actually intensified the resentment and caused renewed agitation.
What These Stories Teach Us: These two accounts teach a crucial and balanced lesson. On the one hand, Mishloach Manot has the potential to be a powerful instrument for peace, friendship, and reconciliation when sent with sincerity and emotional sensitivity. On the other hand, when the relationship is deeply fractured, and especially when hostility remains raw and unresolved, such gestures can be misunderstood, rejected, or even weaponized. They reinforce the idea that while halacha may permit—and in some opinions even encourage—sending Mishloach Manot to an adversary, wisdom and judgment are indispensable. Not every relationship is ready for symbolic gestures. Not every act of outreach will be received as intended.
Sources:
See Orchos Chaim Hachadash 695:9; Piskeiy Teshuvos 695:11 footnote 58; Divrei Sofer 7 p. 19; Hearos Ubiurim Ohalei Torah Vol. 1141 p. 56; Rosh Avos p. 259 (story with Malbim)
Not Yotzei with sending to enemy: Mur Ohalos Ohel Brachos 41
Yotzei with sending to enemy: Sefer Hadarak p. 27 based on Bava Metzia 32b
See regarding the dispute as to the reason behind Mishloach Manos: Terumos Hadeshen 111; Manos Levi towards end; Teshuvas Chasam Sofer 196; Piskeiy Teshuvos 695:9
