Question: Is it correct for one to plead and beseech Hashem for the same thing every single day or is it more proper to pray for a certain matter only several times and if one sees that one has not been answered, one should cease praying for that specific matter?
Answer: The Gemara (Berachot 32b) states: “Rabbi Chanin said in the name of Rabbi Chanina: One who prays lengthily shall merit that this prayer shall not return unanswered. How do we know this? This is derived from Moshe who said, ‘And I prayed to Hashem forty days and forty nights’ and afterwards, the verse states, ‘And Hashem heard me that time as well.’” We see from here that one who prays lengthily (or repeatedly) shall have one’s prayer answered.
The Gemara then questions this, for Rabbi Chiya bar Abba said in the name of Rabbi Yochanan that anyone who prays lengthily and analyzes it shall eventually be disappointed. It seems from this that one should preferably not pray lengthily or repeatedly for one’s requests, for if one does so, one will eventually be disappointed, as the verse in Mishlei (13:12) states, “Hope deferred shall make the heart sick.” The Gemara answers that one refers to praying lengthily and analyzing the prayer while the other refers to praying lengthily without analyzing the prayer.
This means that the teaching of Rabbi Chanina that one should pray lengthily and if one does so, it shall be answered, refers to one who does not “analyze” the prayer, meaning that one does not think all the time that because one prays for so long, the prayer is worthy of being answered. On the other hand, Rabbi Chiya bar Abba’s teaching that one who prays lengthily shall eventually be disappointed refers to one who “analyzes” it by thinking that one’s request will be fulfilled because one prays so lengthily. Because one believes that one’s request will be fulfilled as a result of one’s intense prayer, one’s prayer will not be answered and one will only be disappointed as a result as one hopes for his desires to be fulfilled and in reality, they are not.
Indeed, the Gemara (Berachot 51a) states: “One who prays lengthily shall eventually be disappointed. Furthermore, Rabbi Yitzchak says that one who prays lengthily shall cause one’s sins to be reminded before Hashem.” The Gemara explains that all of these things apply when one “analyzes” one’s prayers. Rashi explains: “One tells himself that one’s request will be granted because one has prayed with concentration.”
Based on this, one should indeed pray repeatedly. One should pray articulately and in the correct places and do so again and again. Even if one has not been answered after one-thousand prayers, it is possible that one more prayer will make the difference and one will be answered. However, one should not grow arrogant and think to one’s self that in the merit of one’s diligent prayer, one’s prayers will be answered. Rather, one should merely wait and hope for Hashem’s salvation humbly. Indeed, the Meiri writes that one should not praise one’s self for praying so intensely and think that he is worthy of the prayer being answered. One should merely act humbly hope for Hashem’s Heavenly mercy and that He act with the attribute of kindness and answer one’s prayer.
Let us now recount a personal incident that happened to us when one of our family members was involved in a complex medical situation. Maran zt”l instructed us to pray for this individual in the “Refaenu” blessing of the Amida. For whatever reason, we ended up praying for this individual in the “Shema Kolenu” blessing as opposed to in the “Refaenu” blessing. Sometime after when the individual had not yet recovered, Maran zt”l inquired, “Why are you not praying for the person in ‘Refaenu’?” Because we were so frightened, we replied, “We are!” Maran exclaimed, “Not true! You did not pray in the ‘Refaenu’ blessing! You prayed in ‘Shema Kolenu’! If you would have prayed in ‘Refaenu’, the individual would already have recovered!”