It is unknown exactly how and where the word hobbledehoy came from, although we do know that it was first used in the 16th century. The noun's playful cadence was used to describe an awkward, youthful person.

Although the origin of the word remains unknown, its use dates back to the middle of the 16th century. Suspicion has focused on French or Anglo-French origins, but no appropriate word has been found there. First element is probably hob in its sense of “clown, prankster” (similar to hobgoblin).

From Scots. Compare dialectal English hobbledygee (“(with a) limping movement”); also French hobereau (“country squire”), English hobby, and Old French hoi (“today”); the original sense may have been "an upstart of today".

[Origin unknown.] from Wiktionary, Creative Commons Attribution/Share-Alike License From Scots. Compare English dialect hobbledygee with a limping movement; also French hobereau, a country squire, English hobby, and Old French hoi today; perhaps the original sense was "an upstart of today".