Hobbledehoy \HOB-uhl-dee-hoy\ , noun;
1. An awkward, gawky young fellow
According to Etymonline.com:
The definition, "clumsy or awkward youth," is attributed from at least 1540. The first element, hob, indicates a sense of "clown, prankster" (like hobgoblin). The second element probably comes from Middle French de haye, which is literally "of the hedge," but it really means "worthless, untamed, wild."
So a 'worthless, untamed, wild clown or prankster' is a dorky teenager?
According to the Oxford English Dictionary:
1. A youth at the age between boyhood and manhood, a stripling; [especially] a clumsy or awkward youth
2. Locally applied by children to a large clumsy top
The etymology offered by the OED is somewhat cumbersome, so I didn't copy it above. It's main idea is that this is a colloquial word and the origin is debatable. The 1540 attribution is mentioned, but so are a few from the 1700's and words such as hoberdidance, hobbididance, and hobidy-booby are listed as possible relatives. It suggest that the word is now frequently associated with hobble, therefore making reference to an awkward of clumsy gait.
To me this word obviously indicates awkwardness of some form - hobble, wobble, bobble; these words all indicated something unsteady. It's the association with a teenager (or a male teenager specifically) that's not outwardly apparent. I suppose teenagers are sort of the epitome of awkwardness, but I digress...
Looking around on the internet, is looks like this word is listed in a bunch of online dictionaries and not much else. It is the name of a montessori school in California, someone's blog (of course), and (like frabjous) an online yarn store. Apparently yarn people like to reach into the random, old-fashioned parts of dictionaries for their store names.
*Today's word and the first definition were both taken from Dictionary.com's 'Word of the Day' for Saturday, September 25