Pray, and Then Pray Again

Vaetchanan. And I emplored …

Five hundred and fifteen.

That’s the number of times, our sages tell us, that Moshe prayed to be allowed to enter the land of Israel.

Prayers Unanswered

Vaetchanan. And I emplored …

Our sages tell us that if our prayers go unanswered, then we should pray again.

But why? If one prayer didn’t help, why would a second or a third?

One answer to this question is that there are certain times that are more auspicious than others for prayer. One example of this is the Thirteen Attributes of Divine Mercy. This prayer is designed specifically to “awaken” Divine mercy. Nonetheless, it’s not to be said at night because mercy, rachamim, is less operative at night, except on the night of Yom Kippur.

In this vein, the Gemora (Yevamot 72a & Brachot 8a) tells us that there are times that are more mesugal, more propitious, for prayer. Since we lack the deep knowledge of knowing precisely when these times are, the Gemora says, it’s wise to be in a regular state of prayer because one never knows when the moment is ripe for acceptance. This can be compared to an inexperienced shooter trying to hit a target. His best chance is to keep shooting in the hope that one finds the mark.

“Why does it say, ‘And as for me, my prayers are to you, God, at the et ratzon, the propitious time.’ He replied, ‘Sometimes the gates of prayer are open, and sometimes they are locked.’ … “Place hope in God, your heart shall be strong and courageous, and place hope in God.’ From here we learn that one should pray, and pray again, and eventually there will be the time for acceptance.” Devarim Rabba, 2:12

Every Prayer is Answered

Our sages offer an alternative answer to the question of why we may need to pray, pray, and pray again. This approach says that in fact all prayers are effective and impactful, however there are times when there exist great impediments, and to overcome those spiritual obstacles requires extra prayer.

V’yeter Yitzchak l’Hashem – And Yitzchak prayed to God …”

Regarding this verse, our sages point to the unusual word v’yeter and say that, “Yitzchak poured forth an abundance of prayers.” They also see an allusion to the concept of “digging” in v’yeter, and compared Yitzchak’s prayers to someone digging a great tunnel through a thick wall. Yitzchak was digging and digging and digging, so to speak, until he was able to break through to the other side.

V’yeter lo Hashem – … And God answered him.”

Here the sages say that like two teams of diggers might tunnel towards one another, God too was digging His way towards Yitzchak’s prayers.

This is a concept that we need to take to heart. As much as we want our own good, God wants it even more. Despite this, there can be times when extenuating circumstances necessitate a delay in the heavenly flow of goodness. At such times, we mustn’t despair, rather we need to redouble our prayers and by doing so we refine and elevate our inner selves. This refining process itself is what can break through the circumstantial obstacles. This can be compared to a father that wants to hand over the reins of his business to a child but knows that he needs to give the young person more time to mature and develop so that he can then be successful in his leadership position.

God Loves Us

This is absolutely critical.

We must never fall into the trap of thinking that prayer is our way of convincing God to do something for us. Nothing could be further from the truth. God loves us and wants every imaginable good for us; even more than we want it for ourselves. However, like a father that knows his children need to grow and develop more before they can fully benefit from the bestowal of the good, the same is true of Hashem. He knows us, and knows every aspect and dimension of our self, and our life, far better and deeper than we ever can. He knows when the time is right, and when it’s premature. For this reason we need to resist the temptation to judge God’s love, and the closeness of our relationship, based on whether or not our prayers are answered.

In response to Moshe’s—

Vaetchanan. And I emplored …

Hashem said, “It’s too much for you. Do not continue speaking to Me about this matter.”

To which Rashi says, “The goodness that is stored away, waiting for you, is far beyond what you are asking for.”

Just Love


Our sages also tell us that the word vaetchanan implies that Moshe was asking for a free gift. He wasn’t saying that his prayers deserved to be answered, that in return for what he, Moshe, had done and achieved in life that it was only right that God respond to his request. No. Moshe was saying: Just love. All I want is to be the beneficiary of Your unconditional love.

There are times when we are embarrassed or ashamed to stand before God. To dare to speak to Him, to ask Him for something. “Who am I to approach God?” These thoughts deflate us and bring us down. From Moshe’s Vaetchanan we learn that when it comes to prayer, to our relationship to God, we can leave all personal considerations aside and know that we are entering into a realm of pure love. A love that is with us and that embraces us, always, whether we think we deserve it or not. A father’s door is always open to his children, and Hashem’s? More so, much more.

Pure love.

“Hashem is close to all who call to Him, to all who sincerely call.” Tehillim 145:18


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Translated and adapted by Shimon Apisdorf