By Rabbi Yochanan Eskenazi
Every person is required to give matanos l'evyonim to two separate aniyim poor people (Shulchan Aruch 694:1). Women are also obligated (Rama 695). Many opinions hold that poor people are also obligated (Mishneh Berurah 694:1). Two matanos are the minimal obligation (Mishneh Berurah 694:3). It is preferable to give more money to the poor than it is to spend on seudas Purim and mishloach manos, because there is greater simcha (joy) than being me'samach (gladden) the hearts of poor people, widows, and orphans, and whoever brings them simcha is comparable to the Omnipresence (Mishneh Berurah 694:3 quoting the Rambam).
One is supposed to give a davar chashuv (respectable amount) (Mishneh Berurah 694:2). There is a dispute amongst the Poskim how much this amount is. Some Poskim hold the amount should be equivalent of the price to buy a respectable meal [for example, 2 slices of pizza and a drink] (Rabbi Herschel Welcher shlit"a, Adar 5772). According to Harav Shmuel Kamenetsky,shlit"a, $1 is considered a davar chashuv (Koveitz Halachos 16:2). When Harav Shlomo Zalman Auerbach zt"l was asked how much one is required to give, he would advise just to make sure, one should give a davar chashuv for both the giver and receiver (Halichos Shlomo Moadim 2:19:ftnt. 62).
One should give matonos ev'yonim on Purim day and not by night (Mishneh Berurah 695:22, Be'ur Halachah 694:1 s.v. l'shnei aniyim). One may write a check for ma'tanos l'evyonim even if it cannot be cashed that day (Koveitz Halachos 16:3 & ftnt. 3 quoting Harav Moshe Feinstein, zt"l). One should not use maaser money for ma'tanos l'evyonim, however, any additional amount of money more than the minimum obligation may come from maaser money (Mishneh Berurah 694:3).
The Shulchan Aruch [694:3] rules "anyone who sticks out his hand [for money] you should give him". In other words this means that on Purim anyone who asks you for money you should give him [and you do not need to check out if he is really a poor or not]. This halachah only applies to someone who is collecting for himself, however if he is collecting for an organization one does not need to give them (Koveitz Halachos 16:1).
Every person is obligated to send two food [or drink] items to one person, as stated in Megillas Esther [9:19] "U'mishalaich manos ish leray'ahu" (Shulchan Aruch 695:4). Both items should be given together at the same time (Koveitz Halachos 17:18 & ftnt. 19 quoting Reb Y.S. Eliyashuv, zt"l). Whoever does more than this, is praiseworthy (Shulchan Aruch 695:4). When one gives his friend mishloach manos, this causes friendship (Shu"T Binyan Tzion 44). The two foods should be two separatetypes of food, but they do not have to be two separate brachos (Koveitz Halachos 17:2). It is preferable to send a food item that is useable as is [and will not need to be cooked] (Mishneh Berurah 695:20). Additionally, they should be something that is acceptable to give to a guest that visits [e.g., a piece of cake, as opposed to just one candy] (Koveitz Halachos 17:6-12). One has only fulfilled his obligation, if the recipient receives his mishloach manos on Purim day (Rama 695:4). Therefore, if one sends mishloach manos before Purim, however the recipient did not receive it until Purim, one has fulfilled his obligation.
There is an opinion that one can only be fulfill his mitzvah of mishloach manos if it is delivered via a shliach (messenger) (Mishneh Berurah 695:18 quoting Shu"T Binyan Tzion 44). The reason is, that Posuk [Esther 9:19] says "U'mishloach" implies that it needs to be sent. Therefore, many people are careful to give at least one mishloach manos via a messenger, to try to fulfill one's obligation according to all opinions.
One should not send mishloach manos to an avel (someone who is in the 12 month mourning period) (Rama 696:6). If someone makes a stipulation that the mishloach manos is for the entire family [and not specifically for the avel] it is ok to send it (Koveitz Halachos 17:41). If one wrongfully sends mishloach manos to an avel [exclusively], the avel may accept it (Koveitz Halachos 17:40). An avel may send mishloach manos to as many people as he normally would have (Koveitz Halachos 17:43).
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