A number of years ago I worked at a company where the chemistry among the people was so wonderful.  I was really fond of the people I worked with.

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Nowadays that means I really liked them.  I have a warm affection for them still.

However 600 or 700 years ago using “fond” when talking bout someone else had quite a different meaning.

Back then it would have meant that they were silly, or even more strongly, that they were blithering idiots.

I look back at the roots of this word and things seem a little misty to me.  On the one hand sources such as Anatoly Liberman’s Word Origins, and etymonline tell me that the earlier foolish meanings of “fond” may be related to the word “fun.”  The Oxford English Dictionary confirms this but and adds that an even earlier meaning of “fond” seemed to be something that was bland and had lost flavor.

I was having trouble making sense of these roots, but maybe an early citation dated 1388 can help out.

“he is said fonned salt, not profitable to any thing”

Which means that somebody is being called a bland spice.  I’m sure you’ve known somebody who was part of your group but was pretty silly and really didn’t add much, or worse was an annoying idiot.  I can see how “fonned salt” meaning “flavorless spice” might have morphed into a meaning of foolish.

The rest of the trajectory of this word is pretty simple.  Already when that quote was made, people were using “fond” to mean “foolish” and as time went on the meaning edged toward the softer meaning, away from an absolute cretin.

Toward Shakespeare’s time “fond” was taking on the tone of “foolishly naive.”  It’s easy to see how one can be sympathetic with naiveté, and so “fond” began to apply to the feelings of that sympathy and affection.

The word “fondle” grew out of “fond” within the last 400 years.  At first it was to treat something fondly and about 200 years ago started to be more specific, in meaning “to caress.”