The Four Cups are a familiar and central Passover Seder observance (which college students need little prodding for). Here’s ten things to know about the Pesach Seder’s Four Cups, in no particular order.
(I see Chabad.org’s extensive Passover website has 12 Facts to Know About the Four Cups – some of what we have below is overlap, but some items are unique to our page here):
(1) The Four Cups at the Seder are rabbinic in origin. They remind us of the Four Expressions of Redemption in the Exodus 6:6-7 (ok, yeh, 6-7), each of which express a different stage or dimension in the redemptive process: “I will take you out”, “I will save you”, “I will redeem you”, and “I will take you to me!” – similar, almost synonyms, but not quite. Each has its own message/goal.
(2) The Four Cups are milestone moments in the Seder journey/evening. The first cup is Kiddush, which sanctifies the holiday and opens to the Seder. Kiddush is Step #1. We drink the Second Cup at the end of Maggid – the long storytelling portion. The Third Cup is for Bentsching/Birkat HaMazon at the end of the “Shulchan Orech” meal – and after the Afikoman Matzah, too. The Fourth Cup is at the end of the Seder.
(3) The Rabbinic Requirement is approx 3 ounces per time. Usually when you hear or think of a cup to drink, you’re thinking 7 or 8 ounces. But not the Four Cups at the Seder. The requirements is 3 ounces. Some customs say to drink the full cup or most of it (regardless of size), so you can just use smaller 4 or 5 ounce cups.
(4) Recline to Left each time. To get the full experience and rabbinic requirement, lean slightly to the left as you drink each of the four cups. This reclining used to be a sign of luxury and freedom. See this post on why we feel his recline is still quite relevant even with modern-day upright dining.
(5) Wine Alternates: Ideally one should drink wine for the Four Cups, the Mishna says we do see even at great cost or even if it afflicts us. Low alcohol wines are fine, too. Grape-Juice is considered a Kosher alternate, but some rabbinic authorities recommend mixing some wine in for a mitzvah like this. For addicts and others for whom this is a very significant risk – one should go grape-juice, or even other non-grape alternates may be an option, speak to your rabbi in such circumstances.
(6) Wine is a Rich Drink. Of the Seder items, Matzah is called poor-man’s bread, but wine is considered a rich drink. Matzah is a plain bread of faith, while wine is a sophisticated complex drink. The Passover Seder seeks both approaches, encourages us to engage on both levels: faith and intellect, simplicity and sophistication…
(7) Source Text Placement. It’s interesting to note that the source of the Four Cups in the Mishna Pesachim is part of a statement that even the extremely poor are required to recline and drink the four cups on the Seder night. Perhaps this Mishna placement is teaching us that the Four Cups are a form of “punching above our weight” for all of us, not only for the extreme financial poor. We’re toasting ourselves and our loves ones, we’re drinking to our spiritual health and growth, we’re hoping and yearning for more!
(8) Cup of Blessing. Jewish Law calls such cups of wine/grape-juice associated with a mitzvah as “Kos Shel Bracha” or cup of blessing. There are laws governing such cups, including that you can’t make a new blessing over already drank from wine. You need to add (even a bit) to make it a new cup of blessing. And ideally such a cup should be full, (even overflowing a bit – to fulfill “our cup runneth over with blessing!”) not filled halfway.
(9) About the Blessing. Usually several cups drank in the same meal are all covered by the first blessing. But not at the Seder. Each cup gets its own blessing (some Sephardic custom differs). Indeed, each cup has its own Seder section and significance, they are part of a set, but each its own cup.
(10) Each Their Own Cup: Not only is each cup unique, but each person drinking it, too. Usually at Shabbat or holiday Kiddush, the leader makes Kiddush and each person just takes a sip. But this night is different! Each person needs their own cup!