The Rama (O.C. 583:1) cites from the Avudraham the well-known custom to eat on Rosh Hashanah a sweet apple with honey and recite a prayer for a “sweet” year. The Maharil (Hilkhot Rosh Hashanah) similarly writes that it is customary to eat sweet foods on Rosh Hashanah as a symbol of our wishes for a “sweet” year.
Interestingly, the Maharil proceeds to suggest allusions in the Tanakh for the connection between the judgment of Rosh Hashanah and “sweetness.” One such allusion, the Maharil writes, is the story of Mara, the place where Benei Yisrael arrived after crossing the Sea of Reeds and then finding no water source for three days. In Mara, they came upon water, but the water not drinkable. God showed Moshe a branch to cast into the water, and after he threw the branch into the water, “va-yimteku ha-mayim” – “the water was sweetened” (Shemot 15:25). The verse then continues, “sham sam lo chok u-mishpat ve-sham nisahu” – “there He placed for them a statute and law, and there He tested them.” While the precise meaning of this verse is unclear, and is discussed by the commentators, the Maharil notes the word “mishpat” in this verse. This word is commonly associated with judgment, and indeed, according to Rashi, the word “mishpat” in this verse means that Benei Yisrael were commanded with regard to civil law. The Maharil suggests that the connection in this verse between the concept of mishpat and the sweetening of the water of Mara alludes to the notion of “sweetness” in the context of the judgment of Rosh Hashanah.
If the Maharil pointed to the story of Mara as a basis for the connection between our judgment on Rosh Hashanah and “sweetness,” then we might perhaps gain deeper insight into this cherished, time-honored practice of eating sweet foods on this occasion. According to the Maharil, the model of sweetness which we commemorate through this custom is not simply a tasty food product, but rather the transformation of something bitter to something sweet. After languishing from thirst for three days, Benei Yisrael finally chanced upon what they thought was the water resource they needed – only to discover that the water was undrinkable. They were exasperated and in despair – but then, in an instant, their crisis was solved; their “bitter” condition was suddenly “sweetened.” We might say, then, that according to the Maharil, we eat sweet foods on Rosh Hashanah to reaffirm our belief in God’s ability to “sweeten” the “bitterness” in our lives. We anticipate not just “sweetness,” but a process of “sweetening.” We trust that the Almighty can solve the difficult, seemingly intractable problems we face in our lives, that He can intervene to guide us towards the “branch” with which we can “sweeten” the “bitter waters.” By eating sweet foods and recalling the sweetening of the waters of Mara, we show that we enter the new year with joy, hope, optimism and excitement, confidently looking to God to eliminate the “bitterness” and grant us the “sweetness” – the joy, contentment and fulfillment – that we crave.