It was not always that way. The original Old English meaning of the word was "happy and blessed." That developed into someone for whom one has sympathy, and so weak in some way. Eventually it took on the current negative meaning. My purpose is to retrieve the original sense of the word.
Some of the saints have also warned against silliness as sinful: frivolous, superficial and distracting from what is good and holy. I do not follow that school of spirituality as I favor the approach of St. Philip Neri, the silliest saint of all, who embodied silly as joy, fun, lightness, affection, freedom.
Silly, for me, is a type of joy, delight, lightness and freedom. It is random, creative, serendipitous, spontaneous. It is freedom from worry, heaviness, obligation, expectation, pressure. It is blissfully void of moralism, perfectionism, indignation, self-righteousness as well as shame, guilt, anxiety.
It is affectionate, at its best.It is shared delight and so is inherently kind and generous.
Silly is a form of humour or comedy. Jim Carey, Robin Williams, Jerry Lewis...all silly! There is an intellectual dimension to silly: the incongruous, the contrarian, the absurd. There is a kind of brilliance to the silliness of a really good comedian.
On the other hand, we must acknowledge an ambiguity to silly: there is a dark side. It is not for nothing that it is disparaged in normal discourse. Silliness in the presence of suffering, sin, evil or tragedy is cruelty. Silliness when insensitive is rude and uncharitable. Silliness as habitual can be compulsive, addictive. In this ambiguity silliness resembles teasing which involves an aggressive and an affectionate dimension: when the former predominates it moves towards abuse, when the later is stronger it is wholesome fun.
As with all things, silly must be guided by sensitivity, prudence, love. Under those conditions, silly is childlike, innocent, liberating...a taste of the Kingdom of God here on earth.
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