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The special foods eaten during Rosh Hashanah are all quite symbolic. Perhaps the most well-known is an apple dipped in honey at the beginning of the Rosh Hashanah meal. Before eating the apple we recite the blessing for fruit, and then the following special prayer: "Yehi Ratzon Milfanecha She'Techadeish Aleinu Shanah Tovah U'Metukah" ("May it be Your will to renew for us a good and sweet year").
As with the apple dip, the honey represents the sweet new year we desire, so we also dip our Challah in honey. Furthermore, there is a custom to eat round challas, sometimes with raisins to increase the sweetness. The idea of something round is that of completeness. We want our year to be wholesome, round and sweet.1
Other customs include the eating of a pomegranate.
Also on the first night of Rosh Hashanah people place on the table the head of either a fish or even a lamb. The head represents (the head of the new year and) our aspiration to always be leading with our head, as opposed to our hearts. As we say in the blessing that we be as the “head and not the tail.”
People also eat fish during the meal since fish represent multiplicity and we ask to be blessed to have children as numerous as the fish in the sea. Fish are also only able to survive within water, and the water is an allusion to the Torah which we refer to as the “living waters.” Therefore, as we eat fish we are reminded that we too should live only through the Torah and like a fish never closes its eyes, so our eyes should always be open to the miracles that surround us.
On the second night of Rosh Hashanah it is customary to eat a "new fruit", a fruit we haven't eaten yet that season. In addition to the symbolism of "new", there is an actual Halachic reason why we eat this fruit. See here for more about this practice.
Footnotes
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