an awkward, ungainly youth.

1530–40; variant of hoberdyhoy, alliterative compound, equivalent to hoberd (variant of Roberd Robert) + -y2 + -hoy for boy (b > h for alliteration; see hob2)

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World English Dictionary
hobbledehoy (ˌhɒbəldɪˈhɔɪ)
archaic, dialect or a clumsy or bad-mannered youth
[C16: from earlier hobbard de hoy, of uncertain origin]

Collins English Dictionary - Complete & Unabridged 10th Edition
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Word Origin & History

"clumsy or awkward youth," 1540, first element is probably hob in its sense of "clown, prankster" (see hobgoblin), the second element seems to be M.Fr. de haye "worthless, untamed, wild," lit. "of the hedge."
Online Etymology Dictionary, © 2010 Douglas Harper
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Example sentences
The hobbledehoy- hood of humanity was long and trying.
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