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Answer: The Rambam (Shabbat 29:1; Sefer Hamitzvot, Aseh 155) is clear on the matter, as he views Kiddush and Havdala as equivalent "bookends": "It is a positive mitzva from the Torah to sanctify Shabbat with words, as it says, "Remember the day of Shabbat to sanctify it" (Shemot 20:7); in other words, remember it as a remembrance of praise and sanctification. One needs to remember it as it enters and as it leaves: as it enters with Kiddush, and as it leaves with Havdala."
Yet, there are notable distinctions between Kiddush and Havdala. Kiddush is done on Shabbat; Havdala is done after Shabbat. Kiddush focuses on Shabbat alone; Havdala distinguishes between Shabbat and chol. Indeed, one gemara (Sh’vuot 18b) seems to put the focus of Havdala on the distinction between Shabbat and chol, rather than viewing it is an appropriate time to praise Shabbat. It cites the pasuk, "To distinguish between the sacred and the mundane" (Vayikra 10:10) as the source for Havdala. One can also argue that Havdala is a way to usher in the weekday, as Shabbat continues (on some level) until Havdala ends it (see Tosafot, Berachot 27b).
Perhaps, whether Havdala relates more to Shabbat or to chol is the basis of a practical question, which Rishonim dispute (both opinions are cited in the Shulchan Aruch/Rama, Orach Chayim 296:8) – are women obligated in Havdala? Women are obligated in Kiddush of Shabbat. Even though it is a time-based mitzva, the positive (zachor) and negative (shamor) mitzvot of Shabbat are linked so that whoever is commanded to refrain from melacha is obligated in Kiddush (Berachot 20b). If Havdala is part of zachor, as the Rambam indicates, women can be obligated from the Torah in Havdala, or even if Havdala is of Rabbinic origin, Chazal could have modeled it after Kiddush (Maggid Mishneh, Shabbat 29:1). The Orchot Chayim (Havdala 18) says that women are exempt from Havdala because it is not linked to the negative element of Shabbat, as the Rabbis only artificially connected it to that pasuk. The Pri Megadim (MZ 296:7) adds on to the Orchot Chayim’s argument that Havdala is done on chol, and therefore it is missing the Shabbat linkage.
One could read into this approach that women are exempt from Havdala because it is a mitzva of chol. The mitzva could be to allow melacha on chol, as it is prohibited to do melacha (all or some – see opinions in Shulchan Aruch, OC 299:10) before a declaration of Havdala (even without wine). However, that seems overstated. The Orchot Chayim probably just means that the chiddush that women are obligated in Kiddush despite it being time-based does not extend to Havdala because Havdala is not as connected to "zachor-shamor" as Kiddush is. All seem to agree that the main point is to stress, as chol begins, how special Shabbat is. Why then is melacha forbidden? One possibility is that until Havdala, it is still, on some level, Shabbat (Mishna Berura 299:33). Another possibility is that one is not allowed to go about normal life before he has fulfilled the mitzva of parting from Shabbat (see Aruch Hashulchan, Tzitz Eliezer XI:34).
Another telling point is the gemara (Berachot 27b) that seems to say (so rules the Shulchan Aruch, OC 293:3; the Mishna Berura 293:9 says not to do this in practice) that Havdala can be made on Shabbat (from plag hamincha). Rav Moshe Feinstein (Igrot Moshe, OC VI:49) says that this is because the Rambam is right that Havdala is a mitzva of Shabbat, even if we usually do it after Shabbat is over. This proof seems refutable (in addition to the fact that early Havdala is only for unusual circumstances) as follows. We find elsewhere that mitzvot that relate to the night can be done (at least according to some opinions) from plag hamincha. Therefore, a declaration of ushering in chol can begin then, even if melacha will certainly be forbidden until nightfall.
Unquestionably, though, the Rambam’s approach, that it is a mitzva of Shabbat, is the most straightforward and accepted one.
Bemare Habazak - Rabbis Questions (654)
Rabbi Daniel Mann
293 - Chazan Starting with Chazarat Hashatz
294 - To What Does Havdala Relate?
295 - How to Tell When Your Tefillin Need Adjustment
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Bemare Habazak - Rabbis Questions Ask the Rabbi: Forgot to Remove Tefillin Before Musaf of Rosh Chodesh
Rabbis in Midrash
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