Pesachim 100 - 106
Havdalah With a Difference
When a Yom Tov festival begins motzei Shabbos (Saturday night) the usual havdalah over wine which ushers out the holy day undergoes an addition and a subtraction.
The addition is the kiddush which declares the holiness of the incoming Yom Tov. There is a difference of opinion among the Sages as to which comes first - kiddush or havdalah. We follow the opinion that kiddush comes first. Two reasons for this are offered by the commentaries.
One reason is that it is more important to declare the holiness (kiddush) of the Yom Tov than to stress the distinction (havdalah) between Shabbos and all other days. Kiddush therefore deserves precedence.
Another reason for putting havdalah second is that putting it first would create the impression that one is eager to be free of the burden of Shabbos and therefore ushers it out at his earliest opportunity.
The subtraction is in regard to the blessing we usually make on besamim (spices or fragrant substances) in our havdalah. Two reasons are offered by the commentaries for deleting this blessing on the eve of a Yom Tov.
One reason is that there is no need for the besamim. The reason we sniff them at the conclusion of a regular Shabbos is to provide comfort for our spiritual essence traumatized by the departure of the neshama yesera (extra dimension of soul) which has been part of us during this soulful holy day. Since we are endowed with a neshama yesera on Yom Tov as well, we suffer no such trauma, and have no need for the comfort of besamim.
Tosefos, however, finds this explanation problematic since it raises the question as to why we do not sniff besamim in the havdalah we make at the conclusion of Yom Tov to comfort us for the loss of our Yom Tov neshama yesera. The alternative explanation offered is that the joy of the Yom Tov and the abundance of delicious food and drink serve the same comforting purpose as besamim and therefore render them redundant.
The Great Kiddush
Upon his arrival in an unfamiliar community, Rabbi Ashi was honored with saying kiddush on wine Shabbos morning on behalf of the congregation.
"Please say kiddusha rabba for us" they requested.
"Kiddusha rabba?" Rabbi Ashi silently pondered. He had never heard that phrase before and he began to wonder what sort of a kiddush was traditionally said in this community. Then he hit on a foolproof plan.
Every kiddush begins with the blessing on wine - "borei pri hagefen." He therefore said that blessing and paused. If no one in the congregation would drink from the cup of wine before him, he would assume that the communal tradition was to say the longer kiddush said on Shabbos eve, and he would continue with its text. When he observed one of the older congregants bending down to partake of his wine, he knew that their tradition was no different from his, and that the kiddush consisted of no more than that one blessing.
But why is this kiddush, which consists of only a single blessing (the passages from Torah and Prophets traditionally recited before the blessing are customary but are not an essential part of the kiddush), called by the paradoxical name of kiddusha rabba - the "great kiddush"?
The Torah commands us to "remember the Shabbos day to sanctify it," which obligates us to verbally declare its holiness. Our Sages directed us to fulfill this command by making this declaration in the kiddush we say at the onset of the holy day, and therefore designed a special text for it which concludes with the praise of Hashem as the "One Who sanctifies the Shabbos." Since the Shabbos meal eaten during the day gives more honor to the holy day than the one at night, our Sages commanded us to make a token kiddush before it as well. But in order to distinguish this kiddush of rabbinic origin from the Torah-mandated one at night, they limited its text to the single blessing on wine.
Rashbam (Rabbi Shmuel ben Meir, grandson of Rashi) explains that this kiddush of a single blessing is accorded this grandiose title because it is the universal opening for every Shabbos and Festival kiddush.
Rabbeinu Nissim (RaN) takes an almost opposite approach by suggesting that this title is a euphemism to cover up the brevity of the kiddush, in the same way that we euphemistically refer to a blind person as "one with much light."