What is the best, most meaningful way to fulfill the mitzvot of “mishloach manot” (sending portions) and “matanot l’evyonim” (giving to the needy) on Purim?

Through a close reading of the text, the Talmud (Megillah 7a) deduces that to fulfill the textual requirement, on Purim we must send two portions of food to at least one friend and two gifts to at least two needy people.  The question of how to make fulfilling this requirement “meaningful” demands going beyond the minima of the law.  Of course, one could make the case that there could be no more meaningful gift to the poor than providing them the basic necessities of life.  Indeed, seeing the faces of the needy receiving an unexpected and appreciated gift would provide the donor with the sense of happiness that 20^th century Rabbi Yechiel Michel Epstein says is the reason behind the requirement in the first place.  Giving to a worthy charity is an alternative.  The consensus among modern authorities is that writing a check to a charitable organization fulfills the Purim obligation.  Consequently, a Jew may decide to donate to an educational, relief, or research organization.   There is no source I can find that relieves us from the requirement of giving portions of food to friends, directly or indirectly (through an agent).  In fact, in today’s depersonalized society the most meaningful way of celebrating Purim may be connecting face-to-face with another human being in a magnanimous way.

Friends usually offer a polite chuckle when I suggest that Purim is the "Jewish" Chanukah, by which I mean to point out that gift giving was/is at the heart of the mitzvot associated with the celebration of the Purim holiday. Further, while the two terms in the question have distinct meanings, tradition links them in a ratio that may have special meaning for our (and any) time. In effect, for each gift to a friend or family member, we should make certain to provide double that number, that quantity or value to assist the needy among us.

 

My own custom is to provide tzedakah in honor of those whom I wish to acknowledge, which, of course, means my friends and family, who have more than enough stuff, have the gift of providing the opportunity by which causes and persons in need will benefit. Chag Purim Sameach!