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Answer: We will peruse some sources in Chazal and later authorities and try to arrive at a balanced approach.
It is a basic Jewish belief (see Rambam’s principles of faith) that a person’s soul exists after death. While basically static, receiving reward and punishment (see Ramban’s Sha’ar Hagemul), the soul is impacted by the actions of relatives and those doing good things to elevate their souls.
Bemare Habazak - Rabbis Questions (657)
Rabbi Daniel Mann
393 - Frozen Challa for Lechem Mishneh
394 - Speaking to The Deceased
395 - Kaddish after An’im Zemirot
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There is a halacha (Yoma 87a; Shulchan Aruch, Orach Chayim 606:2) that seems to include "communication" with a deceased. If one (seriously) insulted someone who subsequently died, he should take ten people to the grave to beg forgiveness. One might claim that this proves that the deceased is aware of the request. However, the recommended language is: "I have sinned to Hashem, and to Ploni, whom I damaged." It is unclear whether the deceased or Hashem is the one/One who needs to listen, or whether just making an admission in the deceased’s "presence" is the important thing.
The sugya to which you refer contains ostensibly instructive elements. The gemara contemplates whether the dead are aware of what is happening in the world and tries to prove it from stories in which live people found out information from the deceased during interactions with them. (The Beit Yosef, YD 179 deals with what separates these cases from forbidden practices of attempted communication with the dead, a topic we are not broaching here). This gemara, though, is not a proof that one can talk effectively to the deceased. Some commentaries (see Maharasha) understand that the living did not communicate but received information in dreams. Also, "sprinkled" through Rabbinic writings are stories of supernatural events, dealt with differently by various commentaries. In any case, we know not to treat something that happened once as something that happens all the time, so we cannot learn from such gemarot of what to expect in our experiences. To the extent that the deceased are able to understand those who visit, it does not necessarily mean that one needs to verbalize to get the message across (their ears do not work, and we are not experts as to the tools their souls use).
A gemara (Sota 34a) tells (at least according to the literal reading) how Kalev spoke to the forefathers in Chevron and asked for their help. While some say one should only ask Hashem to help us in the merit of the tzaddikim (Mishna Berura 581:27) or use a burial place as a holy setting (Derashot Haran 8), others allow asking the deceased to beseech Hashem on behalf of those who visit and/or love them (see Gesher Hachayim I, 29:9; Pri Megadim, EA 581:16). Many good Jews have done so at kivrei tzaddikim and their relatives’ graves over the centuries. (One must be VERY CAREFUL NOT to daven TO the tzaddikim.) One who asks the deceased to pray need not believe that the deceased hear or how. One can "speak" to Avraham Avinu in English or to "Mama Rochel" in Yiddish. It is possible (we do not know) that contemplation and/or set tefillot have the same results. (When we enunciate during tefilla, it is not because we believe that Hashem needs that to "hear us.") It is important that the experience be healthy for the visitor and respectful to Hashem, who decides everything.
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Ha'azinu PURSUIT is PERFECTION
p. Ha'azinu, Shabbat Shuva
Rav Kook deals with the question of the seemingly hopeless nature of Tshuva. For G-d Himself knows that He created us with free will, which inevitably means we will sometimes make mistakes and choose wrong. This can easily be frustrating, freezing us into inaction and ye'ush (loss of hope). If one sins even once, does he chalila have no choice but suicide?! Moreover, our Godly conscience demands justice, righteousness and perfection, but we all know this is impossible, so what's the solution? Rav Kook's innovative thinking, strongly based on chazal (our sages), offers an inciteful and important aspect to this topic, especially this time of year!
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