One of the things I learned when I started learning was that there are three basic categories of questions that people ask in learning. There are regular/yeshivish types of questions; basically, the question that the statement was obviously meant to provoke. For example, the first mishna in Shabbos says there are two ways of leaving a domain which are are actually four. Clearly, one is meant to ask what is the criteria by which the four are grouped into only two? Then there are פלפול/tiny detail/"Brisker chakira" kinds of questions. These can be questions on choice of particular words, grammar, or tense/person. On that same mishna, some of the cases of leaving are actually entering; that's more of a פלפול question. Finally, there are "bala batisha" questions... the kind of thing that are quite obviously off point. Again from this same mishna, the cases are about a homeowner giving/taking to/from a poor person on the street. Those can be interesting (Tosafos right there addresses that question), other time they are "something to think about when you have nothing better to think about"; your mileage may vary.
There is medrash that I have seen discussed a few times -- and is ipso facto famous -- brought by the G"ra in his commentary on משלי/Proverbs 22:9. (You can look it up, if you like; it is outside the scope of this TftD.) The medrash goes that the angels were complaining to HaShem: Your Torah says not to accept a bribe nor to show favoritism, yet You show extreme favoritism to the Jews! HaShem responds, "What can I do? They are stringent to say grace after meals even if they only ate a small amount bread; the equivalent volume of an olive or an egg!" (The Torah requires one to say grace after having eaten a volume of bread equivalent to the size of a large egg.)
It seems to me that the obvious/yeshivish question is: How is that an answer? The Creator seems to be admitting He is taking a bribe! The G"ra did not ask that question. I did, though, and it seemed strange to me that the G"ra did not. Instead, the G"ra asked one פלפול question: Why put olive size before egg size? After all, an olive is about half the size of an egg, so that would seem to be the bigger stringency/surprise. (Surprising thoughts are generally ordered from less to more surprising.) Then the G"ra asks a bala batishe question: I wonder why the medrash chose that particular stringency? We Jews keep oodles of stringencies!
The G"ra gives an answer that addresses his two questions and obviates mine. Says the G"ra, the reason the medrash mentions olive volume before egg is not a matter of being stringent in when we will obligate ourselves in grace. We are obligated by the Torah to say grace after eating an egg volume's worth and by Chazal when eating an olive's volume worth. That is not the question on the table (obvious pun clearly intended). Instead, the medrash is referring to a discussion about the actual amount of food that needs to be eaten to be obligated at a Torah level to say grace. The difference is an olive volume. The question is not whether to nor to say grace, but how do we say grace in the best possible way?
Why is the larger measure then measured? Suppose, says HaShem to the angels, my Jews are just not able to eat the volume required to obligate themselves at the highest level according to all opinions? In that case, they will look to combine with other Jews and even give them enough to eat (the size of an egg) so they can have a group of three or more saying grace together. That is, they will create a זימון. In other words, the Jews use whatever resources they have to find opportunities to do mitzvos.
This is not a bribe; this is a relationship of love. The angels are asking HaShem why he gives special treatment to one group of his servants. HaShem answers, because they aren't servants; they are my children. The reward for both of us is spending more quality time together. I gave them 613 mitzvos and they say, "Wow! 613 different ways to spend time with our beloved Creator!? That's amazing! He must love us as much as we love Him!"
The title for this TftD... "quid pro quo" simply means "you give me something, I'll reciprocate and give you something of equal value". The מִדָה כְּנֶגֶד מִדָה by which we are treated by the Creator has nothing to do with balancing what each side gets. מִדָה כְּנֶגֶד מִדָה means both sides want to figure out how to maximize the giving.
There is medrash that I have seen discussed a few times -- and is ipso facto famous -- brought by the G"ra in his commentary on משלי/Proverbs 22:9. (You can look it up, if you like; it is outside the scope of this TftD.) The medrash goes that the angels were complaining to HaShem: Your Torah says not to accept a bribe nor to show favoritism, yet You show extreme favoritism to the Jews! HaShem responds, "What can I do? They are stringent to say grace after meals even if they only ate a small amount bread; the equivalent volume of an olive or an egg!" (The Torah requires one to say grace after having eaten a volume of bread equivalent to the size of a large egg.)
It seems to me that the obvious/yeshivish question is: How is that an answer? The Creator seems to be admitting He is taking a bribe! The G"ra did not ask that question. I did, though, and it seemed strange to me that the G"ra did not. Instead, the G"ra asked one פלפול question: Why put olive size before egg size? After all, an olive is about half the size of an egg, so that would seem to be the bigger stringency/surprise. (Surprising thoughts are generally ordered from less to more surprising.) Then the G"ra asks a bala batishe question: I wonder why the medrash chose that particular stringency? We Jews keep oodles of stringencies!
The G"ra gives an answer that addresses his two questions and obviates mine. Says the G"ra, the reason the medrash mentions olive volume before egg is not a matter of being stringent in when we will obligate ourselves in grace. We are obligated by the Torah to say grace after eating an egg volume's worth and by Chazal when eating an olive's volume worth. That is not the question on the table (obvious pun clearly intended). Instead, the medrash is referring to a discussion about the actual amount of food that needs to be eaten to be obligated at a Torah level to say grace. The difference is an olive volume. The question is not whether to nor to say grace, but how do we say grace in the best possible way?
Why is the larger measure then measured? Suppose, says HaShem to the angels, my Jews are just not able to eat the volume required to obligate themselves at the highest level according to all opinions? In that case, they will look to combine with other Jews and even give them enough to eat (the size of an egg) so they can have a group of three or more saying grace together. That is, they will create a זימון. In other words, the Jews use whatever resources they have to find opportunities to do mitzvos.
This is not a bribe; this is a relationship of love. The angels are asking HaShem why he gives special treatment to one group of his servants. HaShem answers, because they aren't servants; they are my children. The reward for both of us is spending more quality time together. I gave them 613 mitzvos and they say, "Wow! 613 different ways to spend time with our beloved Creator!? That's amazing! He must love us as much as we love Him!"
The title for this TftD... "quid pro quo" simply means "you give me something, I'll reciprocate and give you something of equal value". The מִדָה כְּנֶגֶד מִדָה by which we are treated by the Creator has nothing to do with balancing what each side gets. מִדָה כְּנֶגֶד מִדָה means both sides want to figure out how to maximize the giving.
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