When the ninth of Av falls on Shabbat, such that the fast of Tisha B’Av is observed after Shabbat through Sunday, it is customary to delay the recitation of havdala until the conclusion of the fast Sunday night. Since havdala requires a cup of wine, and one obviously cannot drink after Shabbat due to the fast, havdala is delayed until Sunday night. Havdala is recited before breaking the fast, because irrespective of Tisha B’Av, Halakha forbids eating and drinking after Shabbat until the recitation of havdala. For the same reason, if a person is ill and thus exempt from fasting, he must recite havdala before eating on Tisha B’Av.
An interesting question arises in the case of a woman who is ill and must eat on Tisha B’Av. Regarding havdala generally, the Rama (O.C. 296:8) rules that women should not recite havdala, and should instead listen to a man recite havdala, due to the debate among the halakhic authorities as to whether women are included in the havdala obligation. The Bach and Magen Avraham, as cited by the Mishna Berura (296:35), dispute the Rama’s ruling, though the Mishna Berura interprets the Magen Avraham’s comments as referring specifically to a case where a woman is not able to hear a man’s recitation of havdala. In such a case, she should recite the berakha, but in general, it is preferable for a woman not to recite havdala for herself. The question then becomes, in the situation of a wife who is unable to fast on Tisha B’Av which is delayed until Sunday, should she recite havdala before eating? Or, should her husband – who is fasting – recite havdala for her, and she would then drink the wine?
At first glance, the latter option would seem preferable. After all, as mentioned, the Rama rules that a woman should not recite havdala for herself, and the Shulchan Arukh elsewhere (271:14) rules that the person who recites kiddush does not have to drink any wine, and can instead give it to one of the people at the table to drink. This ruling is generally assumed to apply to havdala, as well. Therefore, the preferred solution would seem to be for the husband to recite havdala on Tisha B’Av and then give the cup to his wife to drink.
One might, however, challenge this conclusion in light of the ruling of the Shulchan Arukh Ha-Rav (285:1) that if the one who recites kiddush or havdala prefers not to drink the wine, it must be drunk by somebody who fulfilled his kiddush or havdala requirement through his recitation. This means that the cup cannot be drunk by anybody who happens to be present, but specifically by somebody who had listened to the recitation for the purpose of fulfilling the mitzva. By the same token, it may not be given to a young child who has not yet reached the age of chinukh (training in mitzva observance), as he has no mitzva to fulfill, and thus his drinking the wine is of no halakhic significance. As such, one might argue that in the case of a wife who is not fasting on Tisha B’Av, the husband should not recite havdala on her behalf, since he cannot drink the wine, and it is uncertain whether she bears an obligation to hear havdala. According to the view among the Rishonim that women are exempt from the havdala obligation (the position of Tosefot, Berakhot 20b), the husband’s havdala in this case would constitute a berakha le-vatala (blessing recited in vain), as nobody included in the havdala obligation drinks the wine. In light of this concern, one might contend that it is preferable for the woman to recite havdala by herself in such a case, rather than for her to hear it recited by a man and then drink the wine.
It should be noted that even according to this argument, a preferable solution would be to give the wine to a child who has reached the age of chinukh but is not yet old enough to fast (such as a child around the age of seven or eight). Even the Shulchan Arukh Ha-Rav concedes that the havdala wine may be drunk by a minor who has reached the age of chinukh and fulfills his chinukh obligation by hearing the recitation of havdala. This, then, would be the preferred solution in such a case. If, however, no such child is present, then it would seem, according to the Shulchan Arukh Ha-Rav, that the woman should recite havdala by herself.
Rav Asher Weiss, however, rejects this conclusion, as he disagrees with the Shulchan Arukh Ha-Rav’s position. He cites several sources indicating that the person who drinks the wine does not have to be somebody who fulfilled the kiddush or havdala obligation by listening to the recitation, but rather somebody who had heard the berakha over the wine which he or she now drinks. (Specifically, Rav Weiss cites the commentaries of the Rashba and Ritva to Masekhet Eiruvin, 40.) Therefore, returning to our case, even if the wife is exempt from the obligation of havdala, the husband’s recitation suffices to fulfill his havdala obligation, since his wife hears the berakha of “borei peri ha-gefen” over the wine and then drinks. Rav Weiss thus rules that the preferred solution is for the husband to recite havdala for his wife, and then she drinks the wine, unless there is a child present who has reached the age of chinukh but is not fasting, in which case that child should drink. This is preferable to the wife reciting havdala for herself, Rav Weiss asserts, due to the Rama’s ruling mentioned earlier that when possible, women should hear havdala recited by a man rather than recite it themselves.