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Answer: Yom Kippur has a complex character in regard to crying. It is the most important day of teshuva, which includes crying (see Rambam, Teshuva 2:4 & 5:2), but it is also a wonderful day, in that we receive much kapara (atonement) (Vayikra 16:30). In fact, if fasting were not needed as part of the teshuva/kapara process, it would likely be a mitzva to have a feast on Yom Kippur to celebrate the positive (see Ritva, Rosh Hashana 9a).
Rosh Hashana is more complex. The Torah tells us little about the nature of the day, but it is presented as equivalent to the three regalim and Yom Kippur. Chazal tell us that mankind is judged on Rosh Hashana (Rosh Hashana 16a), and due to the real possibility of an unfavorable judgment, we do not recite Hallel on the Yamim Noraim (Arachin 10b). On the other hand, there are powerful, happy things going on, e.g., "coronating" Hashem, hopefully good judgment. The themes associated with the various shofar sounds also conjure up hopeful and foreboding thoughts.
How do these mixed indications of the day’s nature and mood factor into halachic practice? A pasuk in Nechemia (8:10), speaking about a powerful event that occurred on Rosh Hashana, instructs the people not to cry or be sad but to feast on that special day. We indeed pasken along these lines: "We eat and drink and are happy, and we do not fast on Rosh Hashana" (Shulchan Aruch, Orach Chayim 597:1). The Shulchan Aruch does conclude that we should not to eat in a manner that causes lightheadedness, but we should maintain fear of Hashem.
The Gra (see Ma’aseh Rav 207) posits that the above pasuk is a precedent that one should not cry on Rosh Hashana, apparently even during davening. Rav Ovadia Yosef cites others who rule this way and concurs, although he justifies those whose emotions during tefilla bring them to tears (see Yabia Omer IX:51). It is not clear from Nechemia that at no point in Rosh Hashana, including some heart wrenching moments, is one allowed to cry. We note that while the Gra (ibid.) says not to say the powerful tefilla of Avinu Malkeinu, our minhag is to recite it on Rosh Hashana, except when it falls on Shabbat (Rama, OC 584:1).
Bemare Habazak - Rabbis Questions (654)
Rabbi Daniel Mann
579 - Ask the Rabbi: Things that End the Meal and Ramifications
580 - Ask the Rabbi: Crying in Rosh Hashana Davening
581 - Ask the Rabbi: How to Acquire Borrowed Araba’a Minim?
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Multiple sources confirm that the accepted practice is not like the Gra, and most seem to understand that the crying is out of fear of what could happen during the year. Granted, plenty of people do not cry, but realistically, few of those are holding themselves back due to the discipline the Gra promoted (the Gra was famously a highly demanding spiritual person). Rather, some people are not emotionally demonstrative, and some are apathetic to or skeptical about the idea of being judged for the year and how this is critical for their life, an approach that no poskim promote.
Therefore, we assume that those who cry at appropriate junctures enhance their Rosh Hashana and set a good tone for their environs. We strongly discourage faking or artificially amplifying his crying, which in our time and places, is likely and understandably to be scoffed at. Last Rosh Hashana, I was thinking how young people enjoying "smooth" lives have trouble feeling "fear of judgment." Tragically, we have lost many dear people of all ages since then, and it should be easier to feel and demonstrate emotion this Rosh Hashana.
Rabbis in Midrash
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Kuzari -Rabbi Ari Shvat Kuzari class 9 - "Seeing is Believing" (parag. 21-30)
These paragraphs elaborate on the theme that seeing and knowing is better than any attempt to prove logically, and begins explaining the difference between Israel and gentiles.
Ein Aya Various Universal Stages of the Geula Process
Rav Kook examines the various stages of redemption, explaining how (in addition to the obvious oft-mentioned stages of ingathering the exiles, reviving the Hebrew language, army, state etc.) the messianic dream of world prosperity, the State of Israel and world unity can and are realistically and logically gradually coming true.
Kuzari -Rabbi Ari Shvat Kuzari class 8- "Answering Questions on the Kuzari's Proof from Mass Revelation
How do we know that the "claim" of mass revelation to 2,000,000 witnesses at Mt. Sinai is really true? This important class answers all of the questions skeptics ask about this claim of the Kuzari.
Ein Aya Armies Still Necessary for Balance & the War Against Wars
Rav Kook explains why the world was originally divided into the various seemingly contradicting ideologies and cultures, in order to develop each one respectively. Swords or armies symbolize how each respective ideology defends themselves, as well as deters their opposing ideologies and cultures. On the other hand, the messianic era will be one of peace, and Rav Kook explains the transition to that stage, which mankind is already undergoing.
The Land of Israel LGBT'S IN ISRAEL
The question was asked, how can one make Aliyah with the LGBT parades?
Kuzari -Rabbi Ari Shvat Kuzari class 7 - Five Accumulative Proofs of G-d
As a preparation for the Kuzari's classic proof of G-d from the mass-revelation at Sinai, we start here with 5 other directions to strengthen our belief which also contribute to what the Kuzari will present as well.
Ein Aya Muscle & Meaning: The Dual Nature of Gevurah (Physical Strength)
Is physical strength and fitness a necessity or an ideal? Although it if often totally overlooked among topics of Judaism, Rav Kook writes that it clearly is also a necessity to deter the many enemies of Israel, but even in Y'mot HaMashiach, in the Messianic era, to a certain extent, it's ideal continues even after our enemies will have been finished off.
