From http://www.word-detective.com/111097.html#goody Dear Word Detective: What's the origin of the phrase "goody two shoes"? What do two shoes have to do with anything? -- Stephen Jonke, via the Internet. With my luck, of course, one of you will come back and report that the other is too much of a "Goody Two Shoes" to bear and that will be the end of my matchmaking career. "Goody Two Shoes" is a very old slang phrase meaning a good or virtuous person. Today it's often applied to one who hypocritically makes a great show of goodness while actually being somewhat less than virtuous. The original "Goody Two Shoes" wasn't a hypocrite, although she definitely sounds a bit unbearable to modern ears. She made her debut in a children's story called "The History of Little Goody Two-Shoes," published by John Newbery in 1766. Goody was a poor child who only had one shoe. One day she somehow obtained a complete pair of shoes, whereupon she ran through the streets of her neighborhood, accosting passersby at random and announcing "Two shoes! Two shoes!" The author of this fable, incidentally, is said to have been the famed English playwright Oliver Goldsmith. While today we would probably regard Goody as a hopeless wuss and routinely use "Goody Two Shoes" to mean someone who is suspiciously upright, it's comforting to know that it took us almost 200 years to arrive at that conclusion, and that the first negative, cynical use of "Goody Two Shoes" in print dates back only to 1934.