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Posted by Smokey Stover on March 06, 2010 at 21:07

In Reply to: Caddy-corner posted by Mark Perry on March 06, 2010 at 09:21:

: The term caddy-corner refers to something that is not across the street but is diagonally across the street from something. What is the origin of this phrase?

This expression has been spelled many ways, but caddy-corner is a new one. The spelling to use in looking it up in the Oxford English Dictionary is "cater-cornered." It comes from "cater" (pronounced katter), which comes ultimately from French quatre (four), and is used both as a single word and as a prefix. It appears thus as early as 1577 (OED):

"To place or set rhomboidally; to cut, move, go, etc., diagonally. Hence {sm}catering, {sm}catered, ppl. a.
1577 B. GOOGE Heresbach's Husb. 69b, The trees are set checkerwise and so catred [partim in quincuncem directis], as looke which way ye will, they lye level."

As a prefix is has been used in caterways (OED 1874), in caterwise (OED 1875). To "cut cater" was used to mean "cut on the crose," that is, on the bias (OED 1881).

Cater-cornered is often heard as catty-corne, kitty-corner, katty-corners and like variants, always meaning diagonally, or diagonal.

We very commonly think of the word when it means diagonally across the street, but it has also been used to mean diagonally to the street itself (OED 1878). It can be applied to a great variety of situations in which something is placed diagonally to something else. Among the most interesting of the citations of this word given by the OED is the first:

1838 J. C. NEAL Charcoal Sk. 196 One of that class..who, when compelled to share their bed with another, lie in that engrossing posture called 'catty-cornered'.