Inspired by the upcoming holiday of Pesach, where many minhagim seem to have each person drink from his own cup, I was wondering about the custom of drinking wine from the cup upon which kiddush is made on Shabbos (often not directly from the cup, but the same wine that has already been "blessed"). Is there any real reason to do this? We are blessing Hashem, not the wine, correct? (edit: is there possibly a problem vis-a-vis A"Z in treating the wine as blessed?) Why not have individual cups of wine pre-poured at every place, and the leader be motzei everyone? And if so, can the same go for challah?
There are two blessings in Kiddush. There is the bracha over the wine, and the kiddush zman. Is there a distinction between the two such that you can be yotzei the kiddush from the person making it on their cup, but be yotzei the "Borei Pri Hagafen" on your own cup?
Is it necessary to drink from that cup, or just any cup if you had in mind? Also, is there a source for those that pour some wine in everyone's cup before kiddush, and everyone drinks their own little bit after kiddush?
The cup that was used for the mitzvah has a special blessing attached to it. In particular, the Gemara (Berachos 51b) states that with the cup of wine used for the Grace After Meals, it's especially important to give some to the lady of the house. (And it goes on to tell about how Yalta, the wife of the prominent Amora Rav Nachman, was extremely insulted when a guest who had recited Grace declined to do so.)
Aside from this, there is a halachic issue involved. While it is true that the listeners fulfill their obligation by just hearing kiddush, the best way to perform the mitzvah is for them to drink some of the kiddush wine (either directly from the cup, or by having the one who recited kiddush pour some for them). This is noted by Rashbam and Tosafos to Pesachim 100b (s.v. yedei kiddush), and codified in Shulchan Aruch, Orach Chaim 271:14.
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