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    I. Spilling Wine

    Rav Moshe Isserles (Rema, 17th cen, Poland; Shulchan Aruch, Orach Chaim 396:1) records a custom to spill Havdalah wine on the ground. He explains that the basis of this custom is the Gemara (Eruvin 65b) that any house in which wine is not spilled like water does not see blessing. We spill wine during Havdalah in order to start the week on a good note, demonstrating the plenty with which we have been blessed. However, authorities disagree over how and when to spill the wine, if at all, and whether this Talmudic passage serves as an adequate source for the custom.

    Rema says to spill the wine before you finish saying the blessing on the wine. If you spill earlier, the cup becomes deficient (pagum), in some ways as if someone drank from the cup. Similarly, Rav Mordechai Yaffe (17th cen, Poland; Levush, ad loc., no. 1) says to spill the wine only after starting the blessing so that the blessing is not recited on a cup that is pagum. According to both these authorities, you should spill the wine during the blessing.

    Rav David Ha-Levi (17th cen, Poland; Taz, ad loc., no. 1) disagrees with spilling wine. Whether you spill the wine before or during the blessing, the end of the blessing is on a pagum cup and you are showing disrespect to the blessing. Rather, he suggests filling the cup before the blessing until the cup overflows with wine that spills onto the ground. Rav Avraham Gombiner (18th cen., Poland; Magen Avraham, ad loc., no. 3) quotes and objection to this practice because it shows disrespect to the wine. He suggests that we are not concerned when only a little spills out. However, Rav Chaim Yosef David Azulai (Chida, 18th cen., Israel; Machazik Berachah, ad loc., no. 2) says that due to detractors of this practice, those who question its propriety due to the unnecessary spilling of wine, many refrain from this practice.

    II. Sign of Blessing

    Taz questions the very source of this practice. The Gemara (Eruvin 65b) that any house in which wine is not spilled like water does not see blessing. Taz explains that this does not mean that we should intentionally spill wine. Rather, it means that if someone spills wine, we do not get angry over the mistake and instead treat it as if he spilled water. If you remove anger from your home, you will live a life of blessing. Your home will be a place of tranquility, a happy space where everyone can thrive without fear and anxiety. Rav Shmuel Eidels (Maharsha, 17th cen., Poland; commentary to Eruvin, ad loc.) explains likewise.

    While Taz still says to observe this practice by letting a little wine to overflow, Rav Avigdor Nebenzahl (cont., Israel; Sichos Le-Rosh Hashanah, p. 287) sees this as a reason not to spill wine at all before the blessing. Rav Nebenzahl also quotes Rav Menachem Meiri (14th cen., Spain; Beis Ha-Bechirah, Eruvin, ad loc.) who explains the Gemara differently. According to Meiri, the Gemara encourages inviting many guests to your home — Torah scholars and poor people. As you freely share your wine with them, your home will be blessed for this good will.

    III. Second Spill

    Rema (ibid.) writes that we spill the wine a second time after Havdalah and extinguish the Havdalah candle in that spilled wine. Taz (ibid.) objects to this practice. Wine over which a blessing had been recited should not be spilled. However, Magen Avraham (296:4) seems unbothered by this concern. He is, though, concerned with only spilling after drinking from the wine, so as not to interrupt between the blessing on the wine and drinking it.

    Rav Gedaliah Felder 20th cen., Canada; Yesodei Yeshurun, vol. 5, p. 484) suggests that the language of Pirkei De-Rabbi Eliezer (ch. 20, near Radal’s n. 24) implies that you should not spill the wine after drinking from the Havdalah cup. This midrash says that after you drink from the Havdalah cup, it is a mitzvah to pour a little water into it and drink it, in order to show your love for the mitzvah and then to pass what remains in the cup onto your eyes. This is also the practice the Tur (Orach Chaim 299) quotes Rav Amram Ga’on (9th cen., Persia). It seems from here that we should not spill the wine after drinking. Piskei Teshuvos (296:7) quotes Minhagei Chasam Sofer (ch. 6, n. 11) as saying that this was also the practice of Rav Moshe Sofer (19th cen., Hungary).

    In conclusion, some spill the wine during the blessing (Rema, Levush). or allow it to overflow before the blessing (Taz, Magen Avraham). Some do not spill it all at this point (Chida). Some spill the wine after Havdalah (Rema) while others do not (Tur, Chasam Sofer). Everyone should follow their own custom.