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Hobbledehoy is an old Scots word for an awkward rustic adolescent boy or teenager. A hobbledehoy is naïve, gawky, and shy around women. He is neither a boy nor a man, and so is also called a halflin. The root word hob is also used to describe the little men of fairy tales, like hobs, hobgoblins, and hobyahs.

The Hobbit (in a book by Tolkien) is a 3 foot tall man, half the height of a 6 foot man, and therefore a halfling. In Disney's The Legend of Sleepy Hollow, Ichabod Crane, a tall gawky school master, is described as a hobbledehoy in a song, referring to his awkwardness.