Q. Does one comply with the mitzva of shalach manot on Purim, if the gift is send to a neighbor one is not friendly with, since he may not be called “re’eihu”?.
A, On question 2095 regarding if one sends shalach monos and forgot to put a senders card, it fell out or he simply wants to send it anonymously, is he yotzeh, we wrote: “Poskim mention two main reasons for the mitzva of mishloach monos. Trumas Hadeshen (111) maintains it is for the purpose of all having the necessary food available to comply with the Purim seuda. However, Manos Halevy asserts that it is to increase and support friendship and peace.
If one complies when sending them anonymously, would seem to depend on which is the most compelling reason; and indeed Poskim disagree.
Rema (695) rules that if the receiver does not want to accept the shalach manos or returns them, the sender still complies with the mitzva. It would seem that he supports the second reason. However, Mishna Berura (ibid. 24) quotes opinions that disagree (P’ri Chodosh and Chassam Sofer).
Horav Shlomo Miller’s Shlit’a opinion is that the sender does comply with this mitzva after the fact.”
Poskim disagree in our particular case. Orchos Chaim (Spinka) quoting Radak and based on Talmud (Baba-Metzia 32b) mentions he complies, while Mor Veohalos maintains he is not yotze.
Horav Shlomo Miller’s Shlit’a opinion is that if he sends it with the intention of becoming friendly he complies.
Rabbi A. Bartfeld as revised by Horav Shlomo Miller Shlit’a