In one of his columns, Nathan Bierma alerted me to the original meaning of silly, which was quite different from the meaning today. According to the OED, from about 1550 to 1675, silly was used to mean "deserving of pity, compassion or sympathy" or "helpless or defenseless, especially of women and children" or even "weakly, feeble, sickly and ailing." I wonder how and why it evolved to today's meaning. Any ideas? To me, deserving of pity or compassion is quite different from being foolish, which is today's meaning of silly.

It's usually called semantic drift (it's one kind of semantic change). English silly is a classic example. It's change is even wider than you ask about. Silly originally meant 'happy, blissful, lucky; blessed' (still its meaning in the cognate German selig and also cognate with Yiddish zelig used as a name), then 'innocent', then 'worthy of pity', ad finally something like 'foolish'. The earlier meanings of silly are listed by the OED under a different entry seely. It's always hard to say why a word's meaning changes, but there's examples aplenty of it happening. The change between blessed and foolish may have come about with changing attitudes towards saints (holy fools) accompanying the change in brands of Christianity in England in the 16th century. It may be that foolish has changed its meaning over the years. This ties in with a theory about the so-called medieval ship of fools which were mainly filled with undesirables, such as beggars and the mentally ill. (And what are we to make of Mr T's sigature catchphrase? "I pity the fool.")

Yes, I checked the online OED and found seely. What's even more interesting is that its original meaning was "observant of new season, punctual" (from c1200). Then in c1250 it changed to "happy, blissful; fortunate, lucky, well-omened, auspicious."

I guess I am happy when I am punctual.

Interesting, but when I read your post, Kalleh, I misread "deserving of pity" to be "deserving of putty", and I thought, "Well that makes sense, since window sills often require putty." Needless to say, I caught my mistake, but it got me to wondering.

Are sill and silly at all related?

It would be silly even to mention the panes endured by users of Windows.

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Are sill and silly at all related?

From the Online Etymology Dictionary:

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O.E. syll "beam, large timber serving as a foundation of a wall," ... Meaning "lower horizontal part of a window opening" is recorded from 1428.