In a recent re:Play blog post titled “Can a Dictionary be a Toy?”, I wrote about how a pick-up Scrabble game drove me to a word ramble through the pages of an old dictionary for fusty words that begin with the antique prefix “be.”

If you’re a bit of a word fanatic like me, you know that the trouble with looking up words is like the trouble with eating barbeque potato chips—it’s hard to stop with just one. And the other trouble is that this kind of play is contagious. A wry philosopher friend of mine, Carolyn Korsmeyer, caught the bug from my blog and called me to discuss another befuddling trick of the language, the auto-antonym.

“What’s up with the word ’sanction’?” she wanted to know. It can mean either endorse or penalize. And even stranger, what about the word “cleave,” the root that gives us “cleaver,” an implement for separating, and “cleft” as in “already separated.” And for the opposite sense, she quoted “a man… shall cleave to his wife: and they twain shall be one flesh.”

It turns out that words like this are not so antique or rare. An “apology” can be a plea for forgiveness or an aggressive defense. “Clip” can mean fasten to or cut off of. “Custom” can mean a special design or an established way of doing things. “Downhill” can mean that things are declining—going downhill, or the opposite, sliding along and getting easier, as in “it’s all downhill from here!” “Outstanding” can mean either exceptional—outstanding!—or overdue. “Overlook” can mean a panoramic view or to fail to take notice. “Vault” is a locked safe or the soaring sky. If you fight with someone, that can mean you’re against them or alongside them, holding fast.

Once upon a time, I would “bolt” from the room when the babysitter, a sweet elderly neighbor, switched on the Lawrence Welk Show for me and my little brother. (“A one, anda two, anda three….”) But you use a “bolt” to hold one part fast to another. And in fact that brings up “fast,” again. You can hold fast, steadfastly that is, or you can split fast, lickety-split, as I did whenever Joe Feeney, Welk’s ever-present Irish tenor, began to threaten to sing “Danny Boy.”

Now technically, Professor Korsmeyer explained, the auto-antonym is a “homograph,” a word of identical spelling that is itself surprisingly also an antonym—a word of opposite meaning. And that’s why playing with these words is both funny ha-ha, and funny curious. Of course curiosity, in the sense of wonderment not peculiarity, drives play onward.

If this seems a trifling point, consider the word “inflammable.” Maddeningly, inflammable can mean either non-combustible or flammable. To confuse a fire accelerant with the fireproof could be very unfortunate indeed if you were to be holding a lit match or a flaming taper nearby.

Likewise, the taper, which at all costs is not to be confused with a tapir, an auto-antonym in the aural realm, and a snorting pig-like animal of the forest realm with a prehensile snout and sharp teeth. Potential for confusion like this also must have prompted the invention of the words “on-loading” and “off-loading,” so as not to confuse instructions to load or unload, and so avert a donnybrook at the polyglot dockside over a chance pun, a homophone that I’ll call an “aural auto-antonym.”

The question of what’s up with these funny words and why we have them turns out to be several answers.

Sometimes the words have different roots; cleave is one of these, and it’s only coincidence that they sound alike now. English, after all, has been an exceptionally adaptive, welcoming language over the centuries. Or the meaning switches when the verb becomes a noun, as in the instance of “bolt,” above, or “overlook,” or “dust.” Or the psychology of words can migrate; awful once meant “full of awe” and “artificial,” now dismissive, was once a compliment meaning “cleverly designed.” “Begging the question” used to mean building the conclusion into the assumption, a formal logical mistake that I first learned about in a freshman philosophy class where we were encouraged to play with ideas. Now it most often seems to mean a question that urgently deserves an answer, like the one my philosopher friend asked, playfully.

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