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Answer: The gemara (Pesachim 107a) prescribes wine to make Kiddush upon, and this generally applies across the board, for the two Kiddushes of the day, as well as Havdala. (We will not discuss other ceremonial occasions (e.g., brit mila, cup for bentching).) However, we see in a story in the gemara that in a case in which shechar (date liquor) is chamar medina (we will translate it as the major replacement for wine as a central drink), it may be used for Havdala. The gemara then continues to bring the opinion of Rav Huna that shechar should not be used for Kiddush. The Rosh (Pesachim 10:17) views the matter as a machloket Rishonim if the gemara posits that even chamar medina is invalid for Kiddush or whether we could be lenient as we are regarding Havdala.
The Shulchan Aruch (OC 272:9) cites different opinions on whether one can use shechar for Kiddush, but he and the Rama prefer the opinion (attributed to the Rosh) that at night one should not use other drinks as a substitute for wine, but should rather should use challa for Kiddush, whereas in the daytime, shechar is preferable to bread. The Rosh explains the distinction as follows. Bread is the main part of the meal, and Kiddush is closely dependent on the meal, which makes challa the best alternative to wine. However, in the daytime, the essential Kiddush is just the beracha with which one starts the meal (the p’sukim recited are just a preference – Mishna Berura 289:2), whereas at night there is a whole separate beracha of Kiddush. If, then, making Kiddush on challa would consist of saying Hamotzi, it would be the same as if he had a meal without Kiddush.
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One of the problems with chamar medina is that determining what counts as such is very elusive. The simplest reading of the gemara and the opinion of most Rishonim (see Beit Yosef, OC 272) is that it only applies when there is a lack of available wine. The Rambam (Shabbat 29:17) is somewhat more expansive about what is chamar medina (the main drink drunk as wine in that place), although on the other hand he rules that chamar medina may be used only for Havdala and not for Kiddush, apparently even during the day. The Taz (OC 272:6) posits that when wine is expensive (presumably, expensive is relative to the abilities of society and perhaps the person), it is permitted to make Kiddush on chamar medina.
There are few drinks in contemporary society (which likely differ from place to place) that are considered chamar medina according to a consensus of poskim. Whiskey (there is much discussion about how much one must drink) and beer have been on the "short list" for generations (see Shemirat Shabbat K’hilchata 53:9-10), and some have added natural fruit juices and coffee, with milk and soft drinks/soda being "lower on the totem pole" (see ibid.).
In our generation, with a wide variety of wine/grape juice available at cheap prices, the pendulum has rightly turned toward making Kiddush only on them. The best reasons to still use other drinks are when one ran out of them, dislikes them, or has a physical sensitivity to them. Another case is if one is very attached to a family minhag to use a different drink that is indeed still a notable, important drink.
Chemdat Yamim Moreshet Shaul: The Goal of an Agricultural Yeshiva – part I
Based on Siach Shaul, Pirkei Machshava V’Hadracha p. 263 (address at the laying of the cornerstone of the Yeshiva Chakla’it in Kfar Haroeh)
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