Breaking Of The Glass

Our rabbis taught in a midrash, “When ‘will our mouths be filled with laughter’? When the nations (i.e., the Gentiles) say, ‘The Lord has done great things for them.’ Another verse completes this thought, “They will rejoice with trembling.” They said, “In a place of rejoicing there will be trembling.” The explanation is that even in a place where there is rejoicing and joy from doing a mitzvah, there it is necessary that there be some trembling, too, to remember how the world is subject to the evil inclination and is shaken by it, so that it should not be shaken by our joy. Therefore it is a custom in a few Jewish communities at life cycle celebrations and meals celebrating a mitzvah to break there a vessel of glass or “flagons of grapes” to sadden those rejoicing, so that the simhah be mixed a little bit with trembling.

To summarize: The more a person or a people ascends spiritually the greater the challenge to Satan. Satan will "work overtime" to try and entrap people who are on a spiritual high and to drag them down. People who are about to see their life's wish fulfilled by entering marriage, consecrating a house, or by harvesting the first harvest of their vineyards, are therefore at risk because they have reached a situation close to fulfilment of a major aspiration-similar to that of the Jewish people prior to their entry into the Holy Land. The Rekanati also explains the custom of breaking a glass during the wedding ceremony as a "bribe" to the Divine attribute of Justice, much as the proverb about "giving the devil his due."

(1) On the topic of simchah.

(2) An analogy: Sometimes, when people are happy and dance, they grab someone standing outside [the circle] who is depressed and gloomy. Against his will they bring him into the circle of dancers; against his will, they force him to be happy along with them.

(3) It is the same with happiness. When a person is happy, gloom and suffering stand aside.

(4) Yet greater still is to gather courage to actually pursue gloom, and to introduce it into the joy, such that the gloom itself turns into joy. A person should transform gloom and all suffering into joy. It is like a person who comes to a celebration. The abundant joy and happiness then, transforms all his worries, depression and gloom into joy. We find that he has grabbed the gloom and introduced it, against its will, into the joy, as in the aforementioned analogy.

(5) This is the concept of “They will attain gladness and joy, as sadness and sighing flee” (Isaiah 35:10). The sadness and sighing flee and run from joy. For at a time of joy, it is the nature of sadness and sighing to stand aside. Yet one actually has to pursue them, and to catch-up with and reach them, in order to specifically introduce them into the joy.

(6) This is the meaning of “They will attain gladness and joy…” Gladness and joy will catch-up with and seize the sadness and sighing as they flee and run from joy, in order to introduce them, against their will, into the joy.

(7) For there are types of sadness and sighing that are [from] the Other Side. They do not want to be a vehicle for holiness, and so they flee from joy. Consequently, one needs to force them into the holiness, i.e., the joy, against their will.