When faced with an enigma, it is prudent to search in the customs of the festival for a solution. There are two customs that stand out on this mysterious day of Shavuos. One custom is that we are enjoined to remain awake the entire night of Shavuos studying Torah. The second custom is that many Jews eat dairy products on Shavuos. Regarding remaining awake the entire night of Shavuos, the Magen Avraham writes that this custom is based on the Medrash that states that HaShem came to give the Torah to the Jewish People and He found them sleeping. To atone for this lack of zealousness, we remain awake the entire night studying Torah. It is noteworthy that cheese appears to cause drowsiness (See Ralbag Shoftim 4:14) and yet there is a time-honored custom to eat dairy on Shavuos night. This would seem to contradict the idea of staying awake studying Torah.
There are numerous reasons offered for the custom of eating dairy on Shavuos night. One reason mentioned is that the word for milk is chalav, which is in gematria forty, corresponding to the days that Moshe remained in heaven to study and receive the Torah.
Perhaps there is another allusion in this custom of eating dairy. The word chalav, meaning milk, can also be read as halev, the heart, using the principle that the letters ches and hey are interchangeable. When the Jewish People arrived at Mount Sinai, it is said (Shemos 19:2) vayichan sham Yisroel neged hahar, and Israel encamped there, opposite the mountain. Rashi writes that the word vayichan is written in the singular form, to teach us that although all the other journeys throughout the Wilderness were accompanied by strife, this encampment was peaceful, as the Jewish People united like one man with one heart. This teaching is profound, as this essentially defines the receiving of the Torah. We refer to Shavuos as Matan Toraseinu, the giving of our Torah, because we are all together in the study and fulfillment of Torah. One person cannot study Torah alone, as the Gemara (Makkos 10a) teaches us that one who studies alone will become foolish. Choni Hamagal understood this precept well, as upon his return to civilization after sleeping for seventy years, he observed that no one recognized him anymore. He thus requested that he die, and regarding him it was said, “give me a partner or give me death” (Taanis 23a). Rabbi Akiva had twenty-four thousand students, and they all died a horrible death between Pesach and Shavuos because they did not show proper respect to each other (Yevamos 62b).
It is noteworthy that regarding the tribe of Yehudah, who were the teachers of Torah, it is said (Bereishis 49:12) chachlili einayim miyayin uleven shinayim meicholov, red eyed from wine, and white toothed from milk. Rashi writes that this verse is interpreted to mean that it is preferred to smile at someone than to give him a cup of milk. In an abstract manner, we learn from here that cholov should be read haleiv, as friendship is more important than giving one a drink. When two people are in the desert and there is only enough water for one to remain alive, the one who has the water in his possession must drink it, as his life supersedes his friend’s life (Bava Metzia 62a). Yet, one who does not have a study partner and a friend is better off dead.
On Shavuos, we read the book of Rus, and the Medrash refers to this book as Toras chesed, the Torah of kindness. Torah is not merely intellectual stimulation and a study reserved for academia. Rather, Torah is a way of life, where we are enjoined to love each other, similar to the love that HaShem displays towards the Jewish People, as Yisroel, Torah and HaShem are all one. We can now better understand the various titles that are conferred on this mysterious holiday. Shavuos is a time of harvesting, i.e. it is a time when we are enjoined to give to others, by leaving produce in the fields for the less fortunate, as is evidenced from the story of Rus and Boaz. Rus was gathering grain in the fields of Boaz, and subsequently Rus married Boaz and from this union descended Dovid HaMelech, the forefather of Moshiach, our redeemer.