This is just too, too delicious. Just a simple exchange between a gadol b'yisrael and his grandson -- also a talmid chacham of no small measure.
There are now (as of this writing) four volumes of מסורת משה -- halachic questions and discussions between R' Moshe Feinstein, ztz''l, and a grandson, R' Mordechai Tendler. Each night, the introduction explains, R' Tendler would record discussions/questions/interesting exchanges he had had that day with his zeidy. There are, apparently, many years worth of notebooks. They were originally intended as simply notes for himself. At some point, though, several of the other grandsons/grandsons-in-law wanted to arrange and edit those notes into a sefer. They consulted with R' Dovid Feinstein, ztz''l and he told them that he thought it would be a wonderful idea -- on one condition: They needed to have R' Shmuel Fuerst, shilta, review everything before it was published. R' Fuerst agreed and makes sure that all the entries are relevant to practical halacha and not narrow ruling based on some extenuating circumstances.
I spoke to R' Fuerst, shlita, when I saw his haskama and asked if it was fair for me to assume that anything I saw/read/learned in מסורת משה would have the same weight as calling the rabbi. R' Fuerst answered in the affirmative. I now, therefore, feel under no small obligation to learn the relevant מסורת משה entries before calling the rabbi.
So here is the story, which you can find in volume III of מסורת משה, siman 117, page 57. R' Tendler asked his zeidy as follows: Suppose someone is sitting down to eat a small amount of cake/cookie, in fact he plans to eat less than the שיעור/measure that would obligate him in a ברכה אחרונה. Is there any reason that one should not do that, but instead should be careful to eat enough cake/cookie so that he would, in fact, be obligated in making a ברכה אחרונה? R' Moshe answered that there most certainly were compelling reasons to eat a large enough שיעור to require a ברכה אחרונה. First, there is the opinion of the Maharsha that you need a שיעור even for the ברכה ראשונה. Moreover, the actual שיעור of a כזית (k'zayis, literally "like (the size of) an olive", but Google translates as "a tiny amount") is actually quite small. We are stringent to eat a much larger שיעור to cover our bases, but it is very difficult to actually eat so little that a ברכה אחרונה is certainly not required. So, yes, concluded R' Moshe -- when ever eating a snack of cake/cookies, one should strive to eat enough to certainly require a ברכה אחרונה.
R' Tendler thanked his zeidy, and then explained himself, "But I was asking from the mussar point of view; that is, should a person look at the eating as an opportunity to make a bracha and therefore eat an appropriate שיעור?
R' Moshe answered -- and I quote from the sefer -- שמא גם זה ענין/maybe that's also a good point.
Why do I like this story so much? First, this really reinforces that one needs to have a broad knowledge of halacha just to fulfill his obligation. Mussar is crucial, but many of us have a long way to go to simply fulfill our obligations before we even get to the point asking for extra credit. However, what really touched me about this story was that it just feels so real, so human; a zeidy with his grandson.
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