“You like potato and I like [potahto], you like tomato and I like [tomahto] … ”
— “Let’s Call the Whole Thing Off,” George Gershwin and Ira Gershwin, 1937
I prefer caddy-corner. Chances are good that you do not. But let’s not call this whole thing off, hmmm? We might find ourselves quite alone: Google Search suggests at least eight ways of saying this synonym for diagonal and 20 ways of writing it. There’s caddy, catty (pronounced with the same flapped t, but spelled differently), kitty, cata, and cater, any of which can precede either corner or cornered. Hyphens are haphazard and optional. The six most common variants, each with more than 100,000 Google hits, are, in descending order, kitty-corner, caddy-corner, catercorner, kitty-cornered, catty-corner, and catty-cornered.
I did a bit of detective work (an embarrassingly small bit, actually, because the folks at the Oxford English Dictionary had already done everything) and found that by 1519, the French noun quartre had entered the English language as the noun cater, meaning a “four” in dice or cards. (We know this thanks to a certain W. Horman’s unimpeachable, if not overly astute, observation that “Cater is a very good caste.”) But by 1553, cater had moved beyond gambling circles, and by 1577 it had achieved verbhood! It took on the meaning “to place, cut, or move diagonally” as in, “The trees are set checkerwise, and so catered, as looke which way we wyl, they lye leuel.” Cater subsequently succumbed to adverb-dome (as in, “to cut cater”) and joined the adjective cornered to create catercornered.
How this eventually spun itself into 20-odd variants is anyone’s guess. I suspect it may have to do with the “four” sense of cater becoming obsolete: now, cater generally means “serve or provide,” and so catercornered makes no more sense than any of its sound-and-spell-alikes. The word is also used relatively infrequently. People tend to be far more tolerant of variable spellings (and probably pronunciations) for words that appear infrequently than for words that are encountered more often. For instance, in tasks where participants must decide whether or not strings of letters make real English words, psychologists have found that people are less likely to reject misspellings of low frequency words than misspellings of high-frequency words. Really, how could it be otherwise? Teh is obviously a typo, but we’re less certain about opossum versus oppossum—or is it just possum? (The usage experts are adamant—of course they are!—that unless one is “playing possum” it is always opossum.)
In my dialect, incidentally, caddy-corner is used like next: You can be caddy-corner to someone, but not caddy-corner from or directly caddy-corner someone. Despite the additional morpheme –ed, those folks I’ve spoken with who use a -cornered variant have similar intuitions. What about you? And how well do you really know your loved ones? Dig a bit and you might find that some of your best friends, God help you, say kitty-corner.