What makes a great prayer? Are longer prayers more likely to be answered than shorter ones?
The Sages appear to give contradictory counsel. On the one hand, Rabbi Chanina taught that a lengthy prayer will not go unheeded. He learned this from Moses’ extraordinarily long prayer - forty days and forty nights — an impassioned plea that achieved its goal. “And He listened to me also that time” (Deut. 10:11).
Rabbi Yochanan, however, taught the exact opposite. One who prays at length and looks into it — such a person will be disappointed and heartbroken. As it says in Proverbs 13:12, “Deferred hope makes the heart sick.”
The Talmud (Berachot 32b) already took note of this discrepancy. It noted that Rabbi Yochanan specifically spoke of one who ‘looks into his prayer’ — me'ayein bah. What does this mean?
This phrase is traditionally understood to mean one who looks expectantly for his prayer to be fulfilled. Rabbi Yochanan spoke of those who expect that, in merit of their lengthy prayers, they will be answered. Such people, however, are bound for disappointment. Prayers are not automatically answered just because they were recited for a long time. Prayer is not like some automated machine, where, as long as one tosses in enough coins, one’s wish is automatically granted.
Rav Kook, however, gave an original explanation to this Talmudic passage. He explained the phrase me'ayein bah in a more literal way, that it refers to those who examine and analyze their prayers. During prayer, these people reflect on the mechanics of prayer and its deeper function in the universe. While there is nothing wrong with such intellectual inquiry, it creates a serious problem when it takes place during prayer itself.
Prayer is a natural product of the soul’s inner emotions. It should flow from the depths of the soul’s innermost aspirations. Contemplative thought and analysis are useful as a mental preparation and foundation for prayer. By refining our intellectual understanding, and making sure our conduct matches our thoughts and insights, we strengthen the inner soul as it pours out its prayer before its Creator.
But if we combine these calculations and reflections with prayer — during the hour of prayer — that is a mistake. Prayer is not founded on our powers of logic and reason, but on far deeper resources of the soul. Prayer engages the very essence of the soul. It reveals the soul’s inner essence, as it yearns towards the One Who redeems it. When no other mental faculties are admixed with these soul-emotions, then our prayer is purest and most likely to fulfill in its purpose.
Rabbi Yochanan spoke of those who pray at length and examine their prayers. Their prayers are lengthy because of their intellectual contemplations during prayer. These individuals will come to heartbreak, for their prayer is no longer the free expression of the soul’s inner emotions. Their prayer contains foreign elements of intellect and reasoning, and will fail to achieve its true goal.
Now we may understand Rabbi Yochanan’s remedy for those who have fallen in this trap: to engage in Torah study. How will this help?
Those who seek to deepen their cognitive understanding of prayer should do this — not with prayer, but with Torah. This intellectual activity should take place before prayer, as a preparation for prayer. And the more one succeeds in refining one’s cognitive understanding, the more one’s intellect will influence and enlighten the other forces of the soul, the emotions and the imagination.
Those whose prayer is lengthy, not because of reasoned reflections and analyses, but because they strive to bring out the soul’s hidden yearnings and its innate thirst to be close to God — their prayers will be heeded, like the powerful prayers of Moses.
(Adapted from Olat Re’iyah vol. I introduction p. 22; Ein Ayah vol. I p. 150 on Berachot 32b)