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Who is obligated to give Matanos L'Evyonim?
- Both men and women are obligated to give Matanot L'evyonim. 
- Even a poor person who relies on charity to support himself is obligated to give Matanot L'evyonim. 
When should Matanot L'evyonim be given?
- Matanot LeEvyonim should be given during the day and not the night of purim. 
- If one gives Matanot LeEvyonim before purim and is sure that the poor person won’t use it before Purim one fulfilled one’s obligation and some are strict to give it on the day of Purim itself.  Similarly, before Purim one can give it to a messenger (Shaliach) who will give it on Purim itself. 
- One is permitted to give a check.. Some poskim claim that this is only as long as one can draw the money on Purim, meaning the check is not postdated and the banks are open. 
- Does it work to donate Matanot Levyonim in America on Purim for people in Israel if it was already given out before one donated it? Some say that it is effective if the distributor of the Matanot Levyonim does as follows: the distributor can make the money he has belong to the person who will donate the money and then use it for giving Matanot Levyonim. That concept involves having something be effective after the fact but it is effective for Matanot Levyonim.
- One can give money to a distributor of tzedaka which will give out the money to poor people on the 14th and 15th of Adar.
How much does one have to give for Matanot L'evyonim
- One is obligated to give two gifts of charity to two poor people, one to each person. 
- Some say that the amount one should give for each of the poor people is at least Prutah (which is 2.5 Agurot which is a 1/25 of a Shekel)  whereas others say the minimum amount is how much it would cost to buy a meal of 3 KeBaytzim of bread.  It’s proper to be strict for the second opinion. 
- If you give money to someone who distributes money for Matanot Levyonim enough for two poor people one fulfills one's obligation. Even if the distributor really pools all of the money and gives a small percent of all of the money to each poor person and it turns out that one's donation didn't result in an appreciatable amount to two people one still fulfills one's obligation.
Who should one give Matanot L'evyonim to?
- Nowadays, someone who doesn’t have a stable income that can support one’s family for normal expenses and doesn’t have property that’s not usually used and could be sold or if one has abnormal expenses such as for medical bills, or making a wedding for which one can not afford, is considered a poor person regarding this mitzvah. 
- The mitzvah can be fulfilled by giving money to men, women or children. However, if the women and children rely on the father for sustenance, then giving to a father and his child or a husband and his wife would only be viewed as giving to one person .
- One should not check if the poor person is really in need of money, but one should be willing to give to anyone who asks throughout the entire day of Purim. 
What should one give for Matanot Laevyonim?
- One can give either money or food as long as these things can be easily used on Purim. 
- In addition to Matanos Le’evyonim, there is a minhag to give Machatzis Hashekel on erev Purim, before Mincha. In order to fulfill this mitzvah, one should give half a coin of the common currency of his country. 
- There is a custom to give three half coins since it says “Terumah” three times in parshas Shekalim. 
- Machatzis Hashekel is only an obligation for men over the age of 20 because they were the ones who gave the half shekel in the midbar. However, it is customary for everyone to give Machatzis Hashekel. 
- The source for Matanot Laevyonim is found in the Megillah 9:22; Mishna Brurah 694:3, Rambam Hilchot Megillah 2:17, Masechet Sofrim 21:4
- Shulchan Aruch and Mishna Brurah 694:1, Piskei Teshuvot 695:15; ; The Aruch Hashulchan 694:2 explains that although women are obligated, they can fulfill their obligation with their husbands since a man and his wife are considered one entity. He adds that children under bar mitzvah also must give and cannot rely on their father’s giving to exempt themselves
- Shulchan Aruch and Mishna Brurah 694:1; The Aruch Hashulchan 694:2 quotes the Bach, Taz, and Pri Migadim explaining that this obligation of the poor person to give to other poor people is similar to his obligation to sell his possessions in order to buy Chanukah candles and four cups of wine for the Pesach Seder. M.B. 694:2 quotes the Pri Migadim explaining that the poor person can switch meals with two other poor people in order to fulfill his obligation without having to lose money
- Rama 695:5, Magen Avraham 695:13, Mishna Brurah 695:22. Rav Moshe Feinstein is quoted in Balayla Hahu page 19 that if one cannot give during the day one can give at night even before the megilla is read.
- Piskei Teshuvot 694:8, Piskei Shemuot pg 144 quotes Rav Elyashiv who permits lechatchila; Aruch Hashulchan 694:2 says to be stringent and only give on the day itself.
- Piskei Shemuot pg 144 quoting Rav Nassim Karelitz, Sh"t Mahari Assad 207, Daat Torah 695:4, Sh"t Chelkat Yaakov 1:102, Piskei Teshuvot 694:8
- Mishnah Halachot 6:122, Rivevos Efraim 5:455:2 and Halichos Shlomo Purim page 342
- Mishnah Halachot 6:122. Rav Shlomo Zalman Auerbach (Halichos Shlomo Purim page 342) and Rav Belsky (Piskei Harav Belsky pg. 124) explains that one can use a check even if the bank is not open on Purim. Rav Belsky does agree that one should not use a post-dated check.
- Mishnat Hamishpat (Hilchot Tzedaka Biurim 251:2 p. 144) quotes Rav Elyashiv saying that it is effective for the distributor of the tzedaka to be mezakeh the money to the eventual donors and then give it as matanot levyonim and since it is rabbinic we can rely on berierah.
- However, Chevel Nachalato 16:24 p. 143 has a lengthy essay on the topic and concludes that it is ineffective since it involves bereirah and potentially matanot levyonim is divrei kabbalah. Also, since the donor who is supposed to be the recipient of the donation isn't known berierah may not be effective. See there at length.
- Piskei Shemuot p. 147 quotes Rav Chaim Kanievsky saying that it is effective and berierah is irrelevant here, while Rav Karelitz is quoted as holding that one should initially avoid it by splitting up the money for the 14th and 15th.
- In the Gemara Megillah 7a, Rav Yosef says that one should give two gifts to two poor people for Matanot LeEvyonim. Rashi explains that one should give one gift to each poor person. He says that this is derived from the word Matanot, which being in plural means at least 2 gifts, and Evyonim, which being in plural at least 2 poor people. Tur and S”A 694:1 codify this as halacha. Esther 9:22 states, “U’matanos La’evyonim,” in the plural form implying that one is obligated to give to more than one person. M.B. 694:2 quotes the Chidushei Ha’ritva saying that the minimum shiur to give is at least two prutah’s worth, as anything less is not considered a gift. M.B. 694:3 explains that this obligation to give one matanah to two people is only to fulfill the lowest level of the obligation. However, one should try to give as much tzedakah as possible on the day of Purim “for there is no greater simcha than being mesameach a poor person.”
- Mishna Brurah 694:2 quotes the Ritva saying that one fulfills one's obligation even with two prutot (one prutah per poor person). Sh”t Tzitz Eliezer 7:27(7) (at end) seems to agree that this is the accepted halacha
- Shaarei Teshuva 694:1 quoting the Zera Emet 1:11, Maharsha (Megillah 7a), Kaf HaChaim 695:7, Teshuvot VeHanhagot 3:231, Piskei Teshuvot 694:6
- Yalkut Yosef (Kitzur S”A 694:1). Similarly, Yeme Mishteh VeSimcha pg 244 quotes Rav Elyashiv as saying that even though one fulfills one's obligation with a Prutah, nonetheless, it's proper to give each poor person about 5 shekalim which is an amount which would make the poor person happy. Halichot Shlomo (chap 19, note 62) quotes Rav Shlomo Zalman as having said that in order to fulfill all opinions one should give an amount which is significant by the giver and by the taker's standards.
- Mishnat Hamishpat (Hilchot Tzedaka Biurim 251:2 p. 144) writes that we can rely on berierah for the derabbanan mitzvah of matanot levyonim to say it is was as though one gave to two poor people a significant amount. He cites Rav Elyashiv to this effect.
- Chevel Nechalato v. 16 p. 143 quotes Rav Nevinsal who says that matanot levyonim is effective with berierah whether it is derabbanan or deoritta since there’s no need for a specific accomplishment with one person. The goal is just that you gave tzedaka and Hashem considers it as a mitzvah.
- Piskei Teshuvot 694:2
- Aruch Hashulchan 694:2
- S.A. 694:3. The Aruch Hashulchan 694:3 actually learns this statement of the Shulchan Aruch to be a leniency within the obligation of Tzedaka that one can fulfill his obligation of giving Matanos Le’evyonim by giving to almost anyone and he does not have to check to see if they really need money. According to this understanding of the S.A one need not give to every person that asks.
- M.B. 694:2 explains that it is best to give the poor person specifically for his needs on the day of Purim. Thus, food can often be better than money.
- Rama 694:1. The Rama explains that this custom serves as a zecher to the machatzis hashekel that was collected during the month of Adar.
- Rama 694:1
- The Rambam in Hilchos Shekalim 9:7 says that anyone over the age of bar mitzvah should give the half shekel. M.B. 694:5 writes that this is to fulfill the absolute obligation, but the minhag is that everyone should give the half shekel, even a pregnant woman for her fetus.