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Havdalah is the ritual using wine, multi-wick candle, and spices to mark the end of the Shabbat (and holidays) from the beginning of the rest of the week. It acknowledges the distinction between the holy and normative or the sacred and profane in time.
Havdalah consists of four benedictions: over wine, spices, light, and the distinction between the sacred and the profane, between light and darkness, between Yisrael and the nations, between the seventh day and the six workdays.
In Talmudic literature, great importance is attached to the Havdalah: future salvation as well as material blessings are promised to those who recite the Havdalah over the wine cup:
"He who resides in Yisrael, he who teaches his children Torah, and he who recites the Havdalah at the conclusion of the Shabbat will enter the Olam Habah (World to Come)" (Berachot 33a).
Baruch atah Hashem Elo-heinu Melech ha-olam bore' peri ha-gafen
Blessed are You, Hashem, our G-d, King of the universe, Who creates the fruit of the vine.
Baruch atah Hashem Elo-heinu Melech ha-olam bore' minei vesamim
Blessed are You, Hashem, our G-d, King of the universe, Who creates species of fragrance.
Baruch atah Hashem Elo-heinu Melech ha-olam bore' m'orei ha-esh
Blessed are You, Hashem, our G-d, King of the universe, Who creates the illuminations of the fire.
Baruch atah Hashem Elo-heinu Melech ha-olam ha-mavdil bein kodesh lechol] bein or lechoshech bein Yisrael la-amim bein yom hashevi'i lesheshet yemei ha-ma'aseh Baruch atah Hashem ha-mavdil bein kodesh lechol
Blessed are You, Hashem our G-d, King of the universe, Who separates between holy and secular], between light and darkness, between Yisrael and the nations, between the seventh day and the six days of labor. Blessed are You, Hashem, Who separates between holy and secular.
The mnemonic device YaBNeH [Yayin-wine, Besamim-spices, Neir-light, Havdalah-separation/distinction) has been given for remembering the order for Havdalah of Shabbat to weekday (Berachot 52a; also OH, 296:1). Between Shabbat and festival the mnemonic device is YaKNeHaZ (Yayin, Kiddush, Neir, Havdalah, and Zeman) and for Yom Kippur to weekday it is YeNaH (Yayin, Neir, and Havdalah) (Sefer Hamanhig, par. 76).
Each benediction, pronounced with a symbolic act, has specific significance:
Yayin: Wine is used as a symbol of joy and celebration. The Talmud comments, "A person in whose house wine is not poured like water has not attained the state of blessedness." (Eruv 65a) It is customary to pour the wine into a cup so that it overflows, to depict Divine blessing... symbolic of the overflowing blessing expected in the coming week. The wine is also used to douse the Havdalah candle, to indicate that the candle was lit to comply with the spedific precept of Havdalah. The custom of dipping the finger in the wine of the Havdalah and passing it over the eyes alludes to Tehillim 19:9, where G-d's commands are described as "enlightening the eyes." These usages are not applicable whenever the Havdalah is recited as part of the Kiddush for festivals. In addition to the Havdalah over wine, there is another Havdalah inserted in the fourth benediction of the Shemoneh Esreh. In the Sefardic tradition it is customary to put a drop of wine behind the ears, in back of the neck, or over the eyes, and in the pockets as a sign of good fortune for the coming week. (TSLC, pp. 228, 239)
Basamim. According to Maimonides [Rambam], the symbolic use of fragrant spices is to cheer the soul which is saddened at the departure of the Shabbat. We inhale the aroma of the spices because during the Shabbat man is given a neshama yeteirah ("an additional soul"). (Ta'an. 27b; Bez. 16a) At the end of the Shabbat the neshama yeteirah, which is about to leave, grieves, and the smelling of the spices offers comfort to make up for the loss. When a festival follows immediately after the Shabbat the spices are omitted, because the soul then rejoices with the incoming festival. At the conclusion of any festival, spices are not used because the neshama yeteyrah comes on the Shabbat only. Ashkenazim use a combination of cloves and bay leaves for besamim, as well as other pickling spices. In the Syrian synagogue they may use rosewater. In Moroccan communities a myrtle-branch (hadas), rosewater, or various spices are used. Spices or lemon, and, during the summer months, myrtle twigs or mint are often used in Judeo-Spanish communities. (TSLC, pp. 228, 238, 245) According to the Zohar one should use a myrtle twig when making the blessing for besamim. (Cf. Otz Hat, vol. 2, Seder Havdalah) A sign for this practice is the two adjacent phrases in the verse in Sefer Yeshayahu: "Every one that keeps the Shabbat and does not profane it" (Yeshayahu 56:6) and "Instead of the nettle shall the myrtle tree come up" (Yeshayahu 55:13). Thus the blessing for besamim varies in the Sefardic rite: if it comes from a tree, then the formula for the blessing is "Who creates the spice trees"; if it is a type of herb, then one says, "Who creates the herbs of spice"; and if it is neither from trees or herbs, or when in doubt, the formula is "Who creates diverse spices."
Ha-Esh [Neir]. A twisted candle of several wicks is used , because the phrase m'orei ha-esh (the illuminations of the fire) is in the plural. Also, the plural form used when making the blessing over light refers to the different colors contained in the flame: red, white, bluish green. (Ber. 52b; also MB, 298:2) The blessing of light is to commemorate Adam's awareness of being able to kindle a light. He was born on the sixth day of Creation and darkness never descended on earth until the following night. When he saw the sun go down for the first time on Saturday night, he was terrified. G-d gave him the intelligence to take two stones and strike them together. In this manner did man first discover fire. When Adam saw the flame, he exclaimed with gratitude, "Blessed be He, the Creator of light!" (Kol Bo; also Pes. 54a and Bereishit Rabbah 11:2) According to a Talmudic legend, fire was one of the things G-d had left uncreated when Shabbat set in; but after the close of the Shabbat, G-d endowed man with divine wisdom. "Man then took two stones, and by rubbing them together produced fire..." (Pesachim 53b). While pronouncing the benediction over the light it is customary to gaze at the fingernails or palms of the hand. Looking at the nails, in their unceasing growth, is a symbol of the prosperity which, is hoped, the week will bring. (Kol Bo; also Tur in the name of Hai Gaon) The palms of the hand are looked at because the lines of the hand signify something by which to be blessed. (MB, 298:8) Also, the reflection of the light on the fingernails causes the shadow to appear on the palm of the hand, thus indicating the distinction "between light and darkness."
Customarily, Havdalah should be said while sitting, however, the practice is to stand (Otz Hat, vol. 2, p. 868; cf. Baer, Sidd Avod Yis. p. 311) as one accompanies the departure of the Shabbat, that is, to be compared to escorting a king when he departs. (MB, 296:27)
Women are obligated in Havdalah as they are obligated in Kiddush. (MB, 296:34) Rabbi Isaiah Horowitz, known as the Sheloh from the initials of his chief work Sheni Luchot ha-Brit (The Two Tablets of the Covenant) (1), says that women do not drink of the wine of the Havdalah, in allusion to the guilt incurred by Chavah when she gave some of the forbidden fruit to Adam, which is said to have been the juice of grapes.
When making Kiddush in the synagogue on Friday night, it is customary to do so before Aleinu, whereas on Saturday night Havdalah is made after Aleinu. The reason for this procedure is that we are hasty to usher in the Shabbat with Kiddush, but making Havdalah after Aleinu prolongs the Shabbat. (Sefer Matamim - Warsaw, 1889, Sabbath, par. 184)
The concept of Havdalah is ordained by the Torah as part of the general mitzvah to "Remember the Shabbat," the implication being that its differentiation from other days must be verbalized (Rambam - Hilchot Shabbat 29:1).
With the departure of the holy Shabbat and the onset of the work week, it is essential to be conscious of the differences between sanctity and secularity. In explaining why the first mention of the separation is made in the Shemoneh Esreh blessing for wisdom, the Sages explain: "If there is no wisdom, how can one differentiate?" Clearly, then, to distinguish is a function of intelligent reasoning. It is incumbent, therefore upon each Jew to be conscious of the sharp difference between the holiness he has just been experiencing and the sharply lower level of spirituality by which he is about to descend.
Havdalah is traditionally when three stars are visible in the sky, appoximately 20 minutes after nightfall.
Because they loath to lose their extra soul (neshama yeteirah), many Chasidim put off the Havdalah ceremony as long as possible, sometimes until long past midnight. [There are even instances of those who extended the Shabbat until Wednesday, when they began preparing for the coming Shabbat!] Some interpret this 'second soul' as identified with the Shabbat Queen, the Shechinah, who is welcomed every Shabbat. Technically speaking, the arrival of the end of the Shabbat is defined by the ability to recognize three stars, as stated in Mishnah Brachot 1:1. It is at this precise time that a Mitnaged would say Havdalah, but many Chasidim ignored the stars and continued to study Torah for several more hours, unwilling to let go of the spirit of the Shabbat that they so loved.
(1) The Sheloh, or Sheni Luchot ha-Brit, has been described as a profoundly ethical but unsystematic work of Kabbalistic tendencies on Jewish laws and customs. Rabbi Isaiah Horowitz was born in Prague and died in Eretz Yisra'el (1565-1630). He served as rabbi in various communities in Poland, Germany, and Bohemia.
Siddur - Nusach Ashkenazi, p. 618-621
Gabriel's Place - Jewish Mystical Tales, The Three Stars, p. 227, Howard Schwartz
Encyclopedia of Jewish Prayer - Havdalah, p. 169-171, Macy Nulman
Encyclopedia of Jewish Concepts - Havdalah, p. 153-154, Philip Birnbaum