There is a tale of Rosh Hashana in the book of Nechemiah. It was in the initial years of the Return from the exile of 70 years following the destruction of the first Temple.
The crowd that returned was very assimilated — many had intermarried, the people were not well-versed in Torah, and yet they returned to their ancestral homeland to reestablish the commonwealth that had been destroyed by the Babylonians, who were now gone.
Be that as it may, Nechemiah chapter 8 relates the following: “The people gathered to the square that was before the Water Gate, and they said to Ezra the scholar to bring the Torah … and he brought it before the congregation of men and women… on the first day of the seventh month. He read in it … from the [first] light until midday in the presence of the men and the women and those who understood. … And Ezra opened the scroll before the eyes of the entire people. … And Ezra blessed the L-rd, the great G-d, and all the people answered, ‘Amen, Amen,’ with the uplifting of their hands, and they bent their heads and prostrated themselves to the Lord on their faces to the ground. …
“Then Nehemiah and Ezra … said to all the people, ‘This day is holy to the L-d your G-d; neither mourn nor weep,’ for all the people were weeping when they heard the words of the Law. And he said to them,
Go, eat fat foods and drink sweet drinks and send portions to whoever has nothing prepared, for the day is holy to our Lord, and do not be sad, for the joy of the Lord is your strength.’ And the Levites quieted all the people, saying, ‘Hush, for the day is holy, and do not be sad.’ Then all the people went to eat and to drink and to send portions and to rejoice greatly, for they understood the words that they informed them of.”
Rashi says the people were crying because they realized they had not been fulfilling the Torah properly. Ignorant of Torah they may have been, but sincere people trying to do what was right they also were.
When the Tur compares Rosh Hashana to a Judgment Day of anyone in the world, he says people wear black and they may forget to groom, because they don’t know how things will turn out. But we wear white, and wrap ourselves in white, and we shave and cut fingernails, and eat and drink and we are happy and joyous and confident for our outcome.
The Talmud in Sukkah tells us that from the verse “the days of your joy, and your holidays, and your Rosh Chodeshes” we learn that the only Rosh Chodesh not celebrated as Rosh Chodesh, namely Rosh Hashana, is a special day of simcha!
After bringing a number of rabbinic opinions who felt that Rosh Hashana should be a day of fasting, Rabbi Ovadiah Yosef notes that the simple understanding of Nechemiah’s response is that there were people who didn’t understand Rosh Hashana and felt they were supposed to fast! Nechemiah was explaining to them not to fast because Rosh Hashana is a day of joy.
Rav Ovadiah writes that not only is it wrong to cry on Rosh Hashana, but on the contrary, a person should go through the prayers with pleasantness and with joy. Kaddish and kedusha are said with the selichos melody because there is an element of rejoicing which should be accompanied by trepidation. But the overwhelming attitude of this day is one of great joy.
Yet Rav Ovadiah recounts a seeming contradiction. Rabbi Chaim Vital noted how the Arizal cried all day on Rosh Hashana, and even moreso – obviously – on Yom Kippur. And the Ar”i felt anyone who didn’t cry had a soul that hadn’t been self-molded properly.
On the other side, the Vilna Gaon felt that one is NOT ALLOWED TO CRY at all, and he would have the chazzan say a Kaddish with a melody more reflective of Yom Tov than of Selichos.
Rav Ovadiah explains that there is no contradiction. A person should not be making himself cry. But if his intensity and his kavvanah brings him to cry, there is allowance for this. This was certainly the case with the Arizal, who carried the weight of the world on his shoulders because of his deep understanding of the Zohar and the secrets of the universe — he could be drawn to crying. Rav Ovadiah compared this to a known passage about Rabbi Akiva, who would cry on Shabbos when he read Shir HaShirim. When his students asked him how he cries when it is forbidden to be sad on Shabbos, he replied that it was therapeutic for him to cry, citing a fulfillment of oneg Shabbos, enjoying Shabbos.
Perhaps the same means of getting to cry is ok here — if the crying comes from a place of Kedusha, and from a deep connection and longing for clinging to G-d – such as the Arizal approach, rather than out of fear.
Rabbi Ovadiah puts it this way — “but to bring oneself to cry through a mournful act of crying is not permissible.” And he concludes with this important message:
The bottom line is one should not cry on Rosh Hashana. And the prayers of the days should be recited with joy and with holy pleasantness, and with great kavvanah and intensity, for prayer without intent is like a body without a soul. However, one who stirs himself to cry on account of his kavvanah is not violating a prohibition. He should be blessed all the same.
Teshuvah that is accompanied by joy is a fulfillment of what the Tur spoke about — a confidence we have that our repentance and our prayer has been accepted. The two — Teshuvah and joy — go hand in hand.
May we be blessed to enjoy our High Holidays, with the confidence that our joy will carry us to where we need to be when Yom Kippur is over — to a fulfillment of “Serve G-d with joy!”