Should You Keep Praying for the Same Thing? The Talmud’s Guidance on Persistent Prayer

Is it proper for a person to keep pleading with God day after day for the same request? Wouldn’t it be more fitting to pray about it a few times and, if there is no answer, to stop praying about it altogether?

* * *

The Talmud (Berachot 32b) teaches: “Rabbi Chanina said: Anyone who prolongs his prayer — his prayer will not return unanswered. From where do we learn this? From Moshe, as it says: ‘I prayed to the Lord for forty days and forty nights’ (Devarim 9:18), and later it says, ‘And the Lord listened to me that time also.’”

From here we learn that one who continues to pray — who lengthens or repeats his prayers, will eventually have his prayer answered.

However, the Talmud immediately raises an apparent contradiction: “Rabbi Yochanan said: Anyone who prolongs his prayer and examines it will come to heartache.”

This seems to mean that one should not pray too long or too often, because expecting the answer to come through the force of one’s persistence leads to disappointment, as it says in Mishlei (13:12): “Hope deferred makes the heart sick.”

The Gemara resolves this contradiction: “There is no difficulty — one case is when he prolongs his prayer and examines it; the other is when he prolongs his prayer and does not examine it.”

Two Ways of Lengthening Prayer

• When the Sages say that “one who prolongs his prayer will be answered,” that refers to someone who does not examine his prayer — he prays sincerely and humbly, not calculating whether his words are “working.” Such prayer is accepted.

• But when Rabbi Yochanan says that “one who prolongs his prayer comes to heartache,” that refers to one who examines his prayer — who expects his request to be granted because of the strength of his devotion. Since he believes that his persistence will guarantee results, his hopes are often frustrated, and he suffers heartbreak when his wish is not fulfilled.

The Talmud also states (Berachot 55a): “Anyone who prolongs his prayer will come to heartache… and anyone who prolongs his prayer causes his sins to be recalled before God.”

Rashi explains that this refers to one who says in his heart, “Surely my request will be fulfilled because I prayed with such concentration.”

The Right Attitude

It is indeed proper for a person to pray many times, even for the same thing. Even if one has prayed a thousand times without being answered, perhaps one more prayer will bring the desired response.

However, one must never feel self-assured or think, “Because I prayed so much and with such devotion, my request must be granted.” Instead, one should remain humble and continue to hope for God’s abundant mercy, as the Meiri writes: “A person should not take pride in his own prayer or believe that his intention guarantees its acceptance. Rather, he should act with humility and hope for God’s compassion — that He will deal with him kindly and accept his prayer.”

It is not only permissible but praiseworthy to continue praying for the same request — even endlessly. What matters is how one prays: not with entitlement or calculation, but with humility, faith, and trust in God’s mercy.