Bundles of Mitzvot TB Pesakhim 102

The rabbis come out against bundling mitzvot together on today’s daf TB Pesakhim 102. “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 Nahman bar Yitzhak said: Because one does not perform mitzvot in bundles. (אֵין עוֹשִׂין מִצְוֹת חֲבִילוֹת חֲבִילוֹת)” (Sefaria.org translation)

Rashbam explains the reason as one’s relationship to observing the commandments. 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. Tosefot (Moed Katan 8b) gives a different reason why we don’t bundle the mitzvot together while explaining why people are forbidden to marry during the intermediate days of the holiday, hol hamoed. The rabbis did not believe one could multitask successfully and have the appropriate kavanah, intention, for each mitzvah. 

The Gemara teaches we may bundle the mitzvot out of necessity like saying Grace after meals and havdalah over one cup of wine when we only have enough wine for one cup or or when  they are one matter. For example,in the case of making kiddush and havdalah when the holiday begins at the conclusion of Shabbat, they are only one matter. Both mark and draw attention to the sanctity of certain days. 

Tosefot (שאין אומרים שתי קדושות על כוס אחד ד"ה) give an example of the need for two cups of wine because we don’t bundle mitzvot together. At one time Jewish history engagement was separated by marriage by one year and each was consecrated over a cup of wine. Sometime later these two ceremonies coalesced underneath one huppah, marriage canopy. Nevertheless, they remain two separate ceremonies with two different cups of wine even to this very day. The marriage contract, ketubah, is read in between to provide a separation of the two cups  of wine to distinguish between engagement and marriage and the need for the two cups of wine. The same is true when it comes to Grace after meals and the seven wedding blessings. We need two cups of wine because there are two separate  matters.