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There is an interesting principle and ruling established by the Smak, the Tur, and the Rama:

One who davens and did not focus on his prayer, if he knows that he can pray again and focus, he should repeat the prayer, and if not, he should not repeat the prayer (Sefer Hamitzvos Katan***, Mitzvah #11).

This last opinion is expanded upon by the Tur and, in turn, by the Rama (Orach Chayim 101), who rule that should someone fail to have kavanah during the beracha of Avos, he should not repeat his prayer, because of the likelihood that he will not have kavanah the second time around, either.

That was way back when. But we still practice based on this today.

Why do we still assume, despite the enormous amount of Jewish education and the new heights of "frumness" that exists in many Jewish communities, that a person praying will not ever have proper kavanah and so does not repeat the shemonah esrei when their mind wanders?

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Also in the times of the Tur, I bet they couldn't stop checking their iphones... –  Ariel K Jan 10 '12 at 14:24
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Yalkut Yosef vol. 2 pg. 392

אבל אין המנהג בזה כדברי מרן, שסומכים על דברי הטור והרמ''א, שבזמן הזה אין לחזור להתפלל בשביל חסרון כוונה, שהרי אף אם יחזור קרוב הדבר שלא יכוין.

He writes even if you didn't have Kawana on the first Beracha you shouldn't repeat the Amida.

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This just reinforces my question. –  avi Feb 1 '12 at 8:02
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Nowadays, I do think the general rule mentioned in the question still applies. Especially in America, we learn tefillah by rote, because we memorize all the words of tefillah before we speak Hebrew fluently. We therefore have years of practice with lack of havana, and so certainly no kavana. And the length of all of davening decreases the likelihood of true attention to any one part.

Later, hopefully, we know enough Hebrew to understand the words, but given the years of practice, sustained attention requires deliberation and intense focus.

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You really think a person can't read the english and read the hebrew and have kavana? That's what people are paying thousands of dollars for school for? –  avi Jan 10 '12 at 14:19
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A five through seven-year old cannot, and does not. We learn to chant it, not to understand it. Then, when we do have the skills, we don't go back to reevaluate and relearn it with deliberation. My father ran a tefillah teaching group a while back, for college students. He asked, when we say שׁוֹבֵר אוֹיְבִים וּמַכְנִיעַ זֵדִים, to which zeidahs does this refer? And people answered perhaps Esav, as the zeidah of Amalek; or the zeidah of the reshaim. They had never considered it. And though you are right that someone can read the English with Hebrew, it is breaking a habit. –  josh waxman Jan 10 '12 at 15:08
    
oops, looks like I never responded to this comment. When someone says "bad guys", I don't think anyone would ever think about what the author meant by "bad guys", nor are they supposed to. Each person will have their own known "bad guys" of which to apply the bracha that day. It just seems to me that if we said that one must have kavana during davening, instead of assuming that we didn't, that it would be easy enough for people to have the kavana. I know it's easy enough for me. –  avi Feb 1 '12 at 8:05
    
but they thought that 'Zeidim' meant 'grandfathers', not 'bad guys'. My father also asked (this time even educated people), where we say Kivisi Hashem Kivsa Nafshi, why are we comparing ourselves and our souls to a kivsa, a sheep? Why not a para, for example. And he got (from adult, religious, educated people) suggestions that it is a reference to the Akeida... even though that was an ayil. They were a bit embarrassed when he pointed out that it is spelled קותה, rather than כבשה. –  josh waxman Feb 1 '12 at 15:31
    
Heh, I was about to ask what Kivisi Hashem has to do with Sheep, then I read the end of your statement. But the way the question was worded would stump many people. Doesn't mean they don't have kavana when they pray, it just means they are open to suggestive questions, and assumed that the question was a valid one. –  avi Feb 1 '12 at 16:22
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That's a bit of a generalistic idea that a person will not ever have proper kavanah. There are likely many people who are able to pray with the proper amount of kavanah. For the majority of us, however, anything that can take our concentration away is likely to do so when you're trying hard to focus. As an example, try closing your eyes and not think about anything for one full minute. If you're like most of us, your mind will wind up throwing that off within the first few seconds.

If someone dedicates their life to just studying Torah, and has the proper mindset when they daven, they should be able to daven with the proper kavanah.

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I would agree with you, but the halacha as practiced today does not follow that assumption. However when davening our minds are not blank, they are focused on talking to Hashem. When people were mostly ignorant, this would be a hard thing to do. –  avi Jan 10 '12 at 10:12
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