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There are examples in Torah thought that prayers can and cannot reach Hashem. For example, the idea that there are 955 heavens and our prayers can only be carried to the 900th, and we are responsible for making sure they climb the final 55, or the aggadic idea I once heard that one's prayers don't reach Hashem when one has touched a dog. The ideas that the gates of tears are never closed (Berachot 32b). I am not looking for a strictly theological/philosophical/logical solution to this seeming paradox, or to attain a comprehensive understanding of the topic in general or anything, I'm sure that has been asked and dealt with here before.

I am simply looking for well sourced mashalim in helping understand it, on a more intuitive level. For example, it might sound like this:

[Completely made up example] Prayer that reaches Hashem is, l'mashal, when a husband is hearing a message from his wife who he hasn't seen in a year, paying full attention and being very moved, whereas prayers that 'don't reach Hashem' are more akin to a husband who is listening to his wife at a time when he is very busy and distracted l'havdil

Do we have any mashalim? Whether it be Talmudic, Rishonic, from a piyyut or a maggid or chassidishe maaseh, I would love to hear any mashalim you have heard on this concept! I do understand that the whole idea is a "mashal", but hopefully you know what I mean - sometimes it takes more mashalim to help understand a deep mashal!

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אָמַר רִבִּי אִמִּי כָּל־מִי שְׁאֵינוֹ תוֹקֵף לִגְאוּלָּה תְפִילָּה לְמַה הוּא דוֹמֶה. לְאוֹהֲבוֹ שֶׁל מֶלֶךְ שֶׁבָּא וְהִרְחִיק עַל פִּתְחוֹ שֶׁל מֶלֶךְ. יָצָא לֵידַע מַה הוּא מְבַקֵּשׁ וּמְצָאוֹ שֶׁהִפְלִיג עוֹד הוּא הִפְלִיג - ירושלמי ברכות א,א

Rebbi Immi said: Anyone who does not immediately pray after mentioning redemption, whom is he to be likened to? To an acquaintance of the king who comes from afar to the king’s door. When the king comes to see what he wants, he finds that the person left. Hence, the king also leaves. - Yerushalmi Berachos 1:1

פעם נאמר (בישעיהו נ״ה:ו׳) דרשו ה' בהמצאו קראוהו בהיותו קרוב, ואמרו רבותינו ז"ל (יבמות דק"ה ע"א) שזה קאי על עשרת ימי תשובה, ופעם נאמר (בפ' ואתחנן) ובקשתם משם את ה' אלהיך ומצאת כי תדרשנו, וכמו שכתוב (שם בפ' ואתחנן) אשר לו אלהים קרובים אליו כה' אלהינו בכל קראינו אליו, הפירוש הוא דהנה היום בזמן הגלות הוא בנקל להיות נענה בתפלה ולהשיג רוח הקודש יותר מבזמן הבית, כמשל המלך כשהוא בבית מלכותו אי אפשר להתקרב אליו כל כך כמו כשהוא בדרך, שאז יוכל להתקרב אליו כל מי שרוצה, אפילו בן כפר שאינו הגון לבוא לפניו ולדבר עמו, כך היום בגלות, כשהאדם מחשב בדביקות השם יתברך ברוך הוא, אזי שורה עמו ושוכן אצלו, בכן ראוי לאדם שירחק עצמו מן התאוות ומחשבות זרות בכדי שלא יפרד ממנו יתברך, רק יעשה כל מעשיו לשמו יתברך שמו - בעל שם טוב (ראש השנה ויום כיפור, מ״ז)

התפלה שהוא בשמחה גדולה, בוודאי הוא יותר מקובלת לפניו יתברך שמו, יותר מהתפלה בעצבות בבכייה, ומשל על זה כשעני שואל ומבקש ומתחנן לפני המלך בבכיה גדולה אף על פי כן אינו נותן לו אלא דבר מועט, אבל כשהשר מסדר לפני המלך שבח המלך בשמחה ומתוך זה מבקש גם בקשתו, אז נותן לו המלך בקשה מרובה מאוד כמו שנותנים לשררות:(צוואת הריב"ש די"ג ע"א)

Prayer in the midst of great joy is certainly more accepted before the Blessed One than the prayer of sadness and tears. This is similar to a poor person who begs and pleads before the king, crying profusely: nonetheless, the king only gives them a small amount. But when the minister joyfully praises the king, and presents a request alongside it, the king generously gives a much greater amount - Tzava’as Harivash 13a

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Rabbi Yosef Yitzchak Jacobson likened praying to G-d like maintaining a good marriage. It isn't sufficient to just talk to your partner once a month, you'll need to maintain your relationship. How do you do that? By talking to each other. How do you maintain your relationship with Hashem? By praying.

He writes:

You can’t just speak with your spouse and share your life with him/her once a month. To keep a viable, strong, close relationship, you need to spend time together and share what is going on in your life every day. A relationship so powerful needs to be fed and nurtured on a daily basis.

This relationship with Hashem gives men and women resilience and hope. It doesn’t eliminate pain or struggle. It does mean that somebody cares and there is somebody I can talk to. We see this in T’hilim, where King David pours out his heart and shares his feelings and thoughts through each crisis in his life. He shares his fears and traumas and all of his experiences. He sees and feels that Hashem is not deaf to his cry.

As for "prayer reaching Hashem". The Torah relates the story of Yaakov laying down in a place (Har Moriah), and was dreaming that there was a ladder reaching to the Heavens and angels were ascending/descening from it (Bereishis 28:10-13). The Kedushas Levi explains that these angels are the ones that "carry" our prayer and bring them to the Heavenly Throne. I haven't found when our prayers aren't reaching the Heavenly Throne, but I could imagine that it can be due to our sins.

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  • A stunning mashal that has certainly opened my mind and heart to deeper understanding of emes. How does it translate to my exact question: what does it mean for a prayer to "reach" Hashem vs not?#
    – Rabbi Kaii
    Commented Sep 3, 2023 at 15:46
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There are many opinions, some contradictory. Here are three samples:

Prayers said in the synagogue, as part of a congregation, are more effective than prayers said alone at home. They reach the throne of the Almighty more speedily. [Daat Zkenim on Lev. 26:3]

ע. עַל יְדֵי שִׂמְחָה תָּבוֹא תְּפִילָּתְךָ בְּהֵיכַל מֶלֶךְ. By being happy your prayers will reach the chamber of the King. [Sefer HaMiddot, Prayers 1:70]

The gates of tears are not locked [one who cries before God ensures his prayers will be answered], as it is stated: “Hear my prayer, Lord, and give ear to my pleading, keep not silence at my tears” (Psalms 39:13). [Bava Metzia 59a]

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  • Thanks Dr. I don't know if this answers my question though?
    – Rabbi Kaii
    Commented Sep 4, 2023 at 11:09

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