Does God answer every prayer, even when I have prayed for things that did not happen?
The blessing ends by calling God Shome'a Tefillah, the One who hears prayer. The old sources that talk about this are careful not to promise more than that.
Abudarham (a Spanish scholar who wrote a commentary on the prayers in the 1300s) says many people say the line as "You hear our prayers." He prefers the wording we say, "You hear prayers and pleas," because we should not put ourselves so high among the righteous that we claim our prayers are heard all the time. He reads the next line the same modest way: if we have not earned much, do not send us back completely empty, and do at least some of what we asked.
The Gemara is just as honest. A teaching in the name of Rabbi Chanina says that anyone who prolongs his prayer does not come back empty, and he proves it from Moshe. Then the Gemara raises a problem. Rabbi Yochanan says that anyone who prolongs his prayer and keeps looking for the result ends up with heartache. Rashi (the main medieval commentator on the Gemara) explains this as a person who expects the length of the prayer to force the request through, and it does not happen. The Gemara answers that these are two different people: one prolongs, and the other prolongs and waits for the payoff.
Then comes the Gemara's most direct line: "If a person sees that he prayed and was not answered, let him pray again." Its proof is the verse "Hope for Hashem, be strong, let your heart take courage, and hope for Hashem."
So here is what these sources say together: do not assume you have earned a yes, do not treat a long prayer like a lever, and if no answer comes, pray again. None of them promises that every request will be granted. Why some prayers get a no is left open.
Abudarham, Weekday Prayers, Amidah,Berakhot 32b,Rashi on Berakhot 32bI say the same words every day. Is that really praying?
The Mishnah raises this itself. Rabbi Eliezer says that if someone makes his prayer keva, fixed, it is not tachanunim, real pleading.
The Gemara asks what fixed means and gives three answers. For one sage, it is a prayer that feels like a heavy load you want to be rid of. For the Rabbis, it is a prayer not said in the language of pleading. For Rabbah and Rav Yosef, it is a prayer you cannot add anything new to.
Rabbi Zeira admits something easy to relate to: he could add something new, but he is afraid he will get mixed up.
This blessing is where the fixed text opens up. The Gemara says a person asks for his own needs in Shome'a Tefillah, and the Rabbis rule that way. Rav adds that you may also add a request at the end of any blessing that fits it. Someone with a sick person at home adds it to Refa'enu, the blessing for healing, and someone who needs a living adds it to Barech Aleinu, the blessing for the year's crops. Rabbi Yehoshua ben Levi goes further: after the Amidah is over, you may keep asking, even at the length of the Yom Kippur confession.
The Shulchan Aruch (the main code of Jewish law) sums it up: in this blessing a person may ask for all his needs, because it includes all the requests.
So Rabbi Eliezer worries about prayer that is only routine, and the Gemara gives you a place for your own words. It does not say how much to add or how often.
Berakhot 28b and 29b,Avodah Zarah 8a,Shulchan Aruch, Orach Chaim 119:1Is it okay to pray for money, or is that too small a thing to ask God?
Under this blessing the siddur prints a paragraph for asking for food and a living. Here is what the old sources do with that kind of request.
The model is a verse in Mishlei. The writer asks God for two things before he dies. One is to keep lies far from him. The other is: "Give me neither poverty nor riches; feed me my allotted bread." Then he gives the reason: "Lest I become full and deny You, saying, Who is Hashem? Or lest I become poor and steal, and profane the name of my God." He is not asking to be rich. He names the danger on both sides.
Rabbi Meir says a person should always teach his son a clean and easy trade, and also ask for mercy from the One who owns wealth and property. His reason is that poverty and wealth do not come from the trade itself. He brings the verse "Mine is the silver, and Mine the gold" (Chaggai 2:8). So the advice is to do both: work, and ask.
The Gemara describes God's day in four blocks of three hours. In the third block, God sits and feeds the whole world, from the horns of wild oxen to the eggs of lice. The food prayer borrows those words. Asking in them starts by naming a job that is already being done.
The Gemara's short prayer for dangerous roads asks for the same thing in a few words: "Their needs are many and their minds are limited. Give each person enough to live on."
In Mishlei and in that short prayer, the request is for enough, not for a lot.
Mishlei 30:7-9,Kiddushin 82b,Avodah Zarah 3b,Berakhot 29b