No one is quite sure about the origin of the phrase "playing hooky." We consulted the top three online word sleuths and found a number of intriguing explanations.
* The Phrase Finder offers a few possible origins, including "to hook it" or "to escape or make off." To "hook something" is also an old slang term for stealing, as in "stealing a day off."
* The Word Detective dates the first printed use of the phrase to 1848 and relates it to the 19th-century phrase "hooky-crooky," which means "dishonest or underhanded." The parent of this phrase is "by hook or by crook," meaning "by any means necessary."
* Word Origins suggests that the phrase comes from hoekje, the Dutch name for hide and seek.
The phrase seems to be waning in popularity with the younger folks these days. Most kids simply refer to skipping school as "cutting." But regardless of what it's called, the time-honored practice of playing hooky seems here to stay.
From Yahoo Answer