Counting Our Blessings

For the week ending 2 September 2023 / 16 Elul 5783

Havdalah Introduction (part 5): Farewell, My Beloved

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“Hashem, my G-d, will illuminate my darkness”

(King David, Tehillim 18:29)

Havdalah continues with the blessing over the cup of wine: “Blessed are you, Hashem, our G-d, King of the universe, Who creates the fruit of the vine.”

In an earlier essay titled “Kiddush – Part 3” have already explored the blessing over the wine Here we will focus on a beautiful custom that most people have when making Havdalah. When the wine is poured into the cup, there is a tradition to pour in so much wine that it spills over the top and collects in a small puddle underneath the cup.

What is the origin of this custom? In Tehillim 23:5, King David describes his cup as “kosi revayah – my cup is overflowing.” The commentaries explain that Hashem’s blessings are immeasurable, and His goodness overflows on to all those who deserve it. The “cup” is the vessel that holds Hashem’s blessings and symbolizes our lives. When we live as Hashem wants, we become the recipients of His bounty. So much so that His goodness pours over us and His blessings continue to pour out from our own immediate lives into the lives of all those nearest to us as well.

Rabbi Yitzchak Ber Weiss (Siach Yitzchak), points out that the gematria (numerical value) of the word for cup in Hebrew is 86, which is exactly the same gematria as the Name of Hashem denoting strict justice – Elo-him. Rabbi Weiss explains that a cup holds a clearly defined amount of liquid. In the same way, Hashem’s attribute of justice is also meticulously precise. Where there is pure justice, there is no place for mercy. There is no room for anything other than the inflexible and uncompromising truth. When, however, Hashem’s mercy overcomes His attribute of justice, the blessings begin to flow, gaining strength until they pour forth an abundance of goodness.

As we enter the new week, we fill our cup to overflowing. We watch the wine run over the edge of our “Kos Shel Bracha – our cup of blessing.” And we know that all of the blessings that we received over Shabbat will accompany us throughout the coming week as well.

The cup spilling over with wine teaches us that there is always room for more when it comes to spiritual matters. We experience an immeasurably gratifying feeling when we successfully continue to move beyond our spiritual limitations. My Rebbe once taught that our Sages refer to a heaping measure of spices, as used in the Temple, as socheket (see, for example, Tractate Kritut 6b). The word socheket is rooted in the Hebrew word for laughter, sechok. My Rebbe explained that when we overcome our own limitations and successfully demolish the “walls'' that restrict our ability to connect to Hashem, we become the recipients of an overflowing measure of blessing. It is the source of tremendous joy, and a reason to be filled with laughter. This is what our Sages refer to as “middah socheket, a laughing measure.” When we go beyond our physical limitations, we are just like the spoon overflowing with spices.

Therefore, as we face the new week, we are invigorated and excited. We watch as our cup of wine runs over and pours the extraordinary blessings of Shabbat into our week, enhancing and enriching our relationship with Hashem at all times.

To be continued…

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