The following is a brief summary of some of the thoughts said over by R' Frand on the parsha this evening. I have attempted to reproduce these vorts to the best of my ability. Any perceived inconsistency is the result of my efforts to transcribe the shiur and should not be attributed to R' Frand.
R' Frand introduced his vort on the parsha tonight by saying that it may sound like a halachic shiur, but it has a hashkafah/parsha component. Iy'h this will become apparent below.
R' Frand quoted the Rama on Shulchan Orech 296 who states that a person making havdalah should pour out some of the wine on the floor before making the boreh pri hagafen. Why? So that the cup will not be a tainted cup (kos pagum). He continues that any house where they don't pour water like wine will not have a sign of blessing. It concludes that the wine is poured out at this point so that it will be a good sign for the week.
R' Frand polled the audience as to whether anyone pours wine on the floor. There were no positive responses from the audience.
R' Frand followed with a reference to the Taz who says that he does not understand the Rama. What does pouring on the floor have to do with kos pagum? And how can something that we make a blessing on be poured on the floor? Isn't it wasting in violation of ba'al tashchis?
The Taz countered that the minhag is that wine is poured into the cup and the cup is overfilled and a bit spills out on the plate under the cup. (R' Frand said that he did not need to poll the audience, as he is sure that everyone does this minhag).
The Taz continues that the the language of the Rama is retroactive - (b'dieved) if something negative happens, like wine spilling, and the father/master of the house does not get upset, it is a sign of blessing for the house. A person generally will get mad if an expensive bottle of wine spills or something breaks. If this occurs and there is no anger, it is a sign of beracha for the house.
The Taz tied the thought into a gemara in Sotah (3b), where R' Chisda says that anger in the house is like worms for sesame seeds. Much like the worms destroy the seeds, anger destroys the house and causes poverty. If the act is accepted as unfortunate, but no anger occurs, it is a sign of blessing for the house.
R' Frand quoted the sefer B'Zos Yavo Aharon who explains that if there is anger on a loss, it is a sign that the person lacks faith in Hashem. If the person believes in Hashem, then he knows that it is all from Hashem and meant to be this way.
R' Frand closed the vort by saying that we see this concept in the Aseres Hadibros. The first of the commandments is to recognize and know Hashem. The last commandment is not to be jealous of a neighbor. It is easier to accept on one's self that Hashem took the Jews out of Egypt. But if you want to see faith in practice, one must look at how the person deals with adversity. If the person knows and accepts that it all comes from Hashem, he will not be jealous that someone else has a nicer...(you can fill in the blank).
This is the message of the wine spilling over that it is b'dieved - if a person sees that something does not go his way and does not cry over spilled milk, it will be a sign of beracha for him for the week.
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