hobbledehoy

A Hobble-de-hoy is which one of these:
1. 17th century cabinetmaker's tool used for drilling peg holes in hard woods.
2. A young shepherd.
3. An affectionate greeting between crippled sailors.
4. Nonsense, confusion. Also a stew of vegetables, meat, and broth; hotchpotch.
5. An awkward, callow youth.
6. A wooden toy of colonial times; currently still made in remote mountain communities.
7. A mariner's cry when a whale becomes entangled in a harpoon line.
8. Trade name for a breakfast cereal made from a species of seaweed.

You will not find a better description of the type than in Anthony Trollope’s The Small House at Allington:

“Such young men are often awkward, ungainly, and not yet formed in their gait; they straggle with their limbs, and are shy; words do not come to them with ease, when words are required, among any but their accustomed associates. Social meetings are periods of penance to them, and any appearance in public will unnerve them. They go much about alone, and blush when women speak to them.

In truth, they are not as yet men, whatever the number may be of their years; and, as they are no longer boys, the world has found for them the ungraceful name of hobbledehoy”.

But where the world found it is far from clear. The word seems to have been around at least since the sixteenth century, but was long distinguished by seeming never to be written the same way twice. It may well be related to Hoberdidance or Hobbididance, which was the name of a malevolent sprite associated with the Morris dance (and whose name is from Hob, an old name for the Devil; nothing to do with hobbits). It may also be linked to hobidy-booby, an old English dialect word for a scarecrow. The modern spelling seems to be the result of popular etymology, which has changed a puzzling word into something that looks as though it might make more sense.

Today they are known as geeks :~))

Hobble-de-hoy! is a published version of an old parlor game, Dictionary.  The book contains complete instructions, a word list of 1001 words, and, in the back of the book, definitions from the Oxford English Dictionary for the 1001 words.
The book can be opened from either end - flip it over, and it appears to be right-side up from either side. One side brings you to the word list, the other to the definition list. Each word and definition are numbered so you can match them up easily.
The word list is a very interesting selection of some of the more obscure words in the Oxford English Dictionary.  In this book, you won't recognize at least 98% of the words! The title of the game is one such word, meaning an awkward, callow youth.