Rabbi Yosei maintains that once they have finished their meal, they bring out two cups; over the first cup one recites the Grace after Meals, and over the second cup he recites the sanctification of the day. The Gemara asks: Why do they need two cups? And let them say both of them, Grace after Meals and kiddush, over one cup.

Rav Huna said that Rav Sheshet said: One does not recite two sanctifications, i.e., for two mitzvot such as Grace after Meals and kiddush, over one cup. What is the reason for this halakha? Rav Naḥman bar Yitzḥak said: Because one does not perform mitzvot in bundles. If someone performs multiple mitzvot all in one go, he gives the impression that they are a burdensome obligation that he wants to complete as fast as possible.

And does one not perform multiple mitzvot together? But wasn’t it taught in a baraita: One who enters his home at the conclusion of Shabbat recites the blessing over the wine, and then over the light, and then over the spices, and thereafter he recites havdala over the cup of wine. And if he has only one cup of wine, he leaves it for after he eats his food, and uses it for Grace after Meals, and arranges all of the other blessings together thereafter. This baraita indicates that one may use the same cup both for Grace after Meals and havdala. The Gemara answers: We cannot prove anything from here, as a case where one does not have an additional cup is different. One who has two cups of wine is required to recite Grace after Meals over one of the cups and havdala over the other one.

The Gemara continues its line of questioning: But there is the case of a Festival that occurs after Shabbat, when presumably one has enough wine. And nevertheless, Rav said that the proper order of the blessings is according to the Hebrew acronym yod, kuf, nun, heh: The blessing over the wine [yayin], kiddush, the blessing over the candle [ner], and havdala. This ruling shows that one recites kiddush and havdala over the same cup of wine.

They say in answer to this question: From the fact that Rav did not say that one recites the blessing for time, Who has given us life [sheheḥiyanu], sustained us, and brought us to this time, this proves by inference that we are dealing with the seventh day of Passover, which is the only Festival day on which one does not recite the blessing for time. If so, it is possible that whatever wine this person had, he has already consumed over the course of the Festival, and he does not have enough wine left for two separate cups.

The Gemara asks: But there is the case of the first Festival night that occurs after Shabbat, when one has wine, and nevertheless Abaye said that the order of the blessings in this instance follows the Hebrew acronym yod, kuf, zayin, nun, heh: The blessing over wine [yayin]; kiddush; the blessing for time [zeman]; the blessing over the candle [ner]; and havdala. And Rava said that the order of the blessings is in accordance with the acronym yod, kuf, nun, heh, zayin: Wine [yayin]; kiddush; candle [ner]; havdala; and the blessing for time [zeman]. Although Abaye and Rava dispute the correct order of the blessings, they agree that one recites multiple blessings over a single cup of wine.

Rather, the Gemara rejects the previous explanation in favor of the following: Havdala and kiddush are one matter, as they both mark and draw attention to the sanctity of certain days. By contrast, Grace after Meals and kiddush are two entirely different matters. Therefore, one who recites both of them over the same cup of wine is combining two unrelated mitzvot, apparently so that he can be done with them as quickly as possible. Consequently, this practice is prohibited.

After raising the issue of the proper order of the blessings for kiddush on a Festival that occurs right after Shabbat, the Gemara addresses the matter itself. With regard to a Festival that occurs after Shabbat, Rav said that the proper order of the blessings follows the acronym yod, kuf, nun, heh: Wine [yayin], kiddush, candle [ner], and havdala; and Shmuel said the proper order is yod, nun, heh, kuf: Wine [yayin], candle [ner], havdala, and kiddush.