Don’t Cry Over Spilled Wine

There is a widespread custom mentioned by the Rema (296:1) to spill some wine by Havdalah as a good omen for blessing. However, this custom has many poskim seeing red. Instead of relying on what you may have heard through the grapevine, let us examine the source.
The Gemara says in Eiruvin (65a), Rebbe Chanin bar Papa said: Whoever does not have wine spilled in his house like water is not included in the category of those blessed. As the verse states ‘U’verach es lachmecha v’es meimecha,’ and He will bless your bread and your waters. Rebbe Chanin reasons that just as the bread referred to in the verse can be purchased with maaser sheni funds, similarly the water mentioned in the verse must also be able to be purchased with maaser sheni funds. Since one may not buy water with maaser sheni funds, perforce the water in the verse must refer to something else, namely wine. Why does the Torah refer to wine as water? To teach us this lesson: If the wine in your house is spilled like water you are in the category of blessed.