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The first stage of the Seder is "Kadesh," the recitation of Kiddush. This Kiddush serves two functions: it fulfills the obligation of Kiddush that applies every Shabbat and Yom Tob, and constitutes the first of the four cups of wine that one is required to drink on the night of Pesah.
Since all four cups must be drunk specifically on Pesah, one should not recite Kiddush on Pesah night until Set Ha’kochabim (nightfall). It is not necessary to wait until Set Ha’kochabim as defined by Rabbenu Tam (seventy-two minutes after sundown); one may begin the Seder at Set Ha’kochabim as defined by other opinions, approximately 35-40 minutes after sundown (in New York City). In practice, however, this issue is rarely relevant. By the time one comes home from the synagogue and everyone assembles and prepares to begin the Seder, it is usually Set Ha’kovachim according to Rabbenu Tam’s opinion.
One should preferably use for the Seder red wine that is not Mebushal (meaning, that had not been boiled). Some problems can arise when using wine that is not Mebushal, as it becomes forbidden if it is handled by a gentile. Nevertheless, one should preferably obtain this kind of wine for the Seder, and exercise care to ensure that it remains permissible. Of course, one who cannot obtain wine that is not Mebushal may use Mebushal wine. Likewise, one who will become ill or will not feel well if he drinks four cups of wine may use grape juice for the four cups of wine at the Seder.
It is customary not to pour one’s own cup of wine at the Seder, and to have the person sitting next to him to pour for him, instead.
According to Kabbalah, one must wash the cup – both the interior and exterior – before Kiddush, even if it is clean. Furthermore, one should pour three drops of water into the cup after he pours the wine, before reciting Kiddush.
Each of the four cups of wine must be drunk all at once. It is improper to take a sip, pause, and then sip some more; the entire cup should be drunk all at once, without interruption.
The cup of wine should hold at least 3.3 oz. of wine. If one finds it difficult to drink the entire cup, he must drink at least 1.6 oz.
The four cups of wine must be drunk while reclining ("Heseba"). The authorities debate the issue of whether one who mistakenly drank without reclining must drink another cup of wine. Hacham Ovadia Yosef held that one should drink another cup if he drank without reclining. The Hida (Rav Haim Yosef David Azulai, 1724-1806), however, maintained that one does not have to drink another cup in this case. He notes that the Gemara does not require reclining while drinking all four cups, but rather while drinking two of the four cups. We recline for all four only because we are unsure which of the two cups require reclining. Furthermore, the Re’avya (Rabbi Eliezer Ben Yoel Halevi, Germany, 1140-1225) held that nowadays we are not required to recline at all during the Seder. Hence, since we have two reasons to question the obligation to recline regarding each cup, we may be lenient in a case where one mistakenly drank without reclining. This is indeed the Halacha; one who forgot to recline while drinking one of the four cups need not drink another cup. (This is especially so regarding women, as some authorities held that women are not required to recline at the Seder. Even though we do not follow this view, and we require women to recline, a woman who drank one of the cups of wine without reclining is not required to drink another cup.)
It must be emphasized that this discussion pertains only to the four cups of wine. With regard to Masa, one who ate Masa at the Seder without reclining must eat another Kezayit while reclining.
The one who recites Kiddush at the Seder must have in mind that the others will fulfill their obligation through his recitation, and the others must have this intention, as well. As he recites the Beracha of Sheheheyanu, everyone must have in mind that the Beracha should refer to the occasion of the Yom Tob, and to all the Misvot that apply that night – the four cups of wine, Masa and Marror.
