"The Hatter opened his eyes very wide on hearing this; but all he SAID was, 'Why is a raven like a writing-desk?'

'Come, we shall have some fun now!' thought Alice. 'I'm glad they've begun asking riddles.' 'I believe I can guess that,' she added aloud.

'Do you mean that you think you can find out the answer to it?' said the March Hare.

'Exactly so,' said Alice.

'Then you should say what you mean,' the March Hare went on."

-- Alice in Wonderland, Chapter VII, by Lewis Carroll.

Alice never did guess the answer; the tea party proved to be too chaotic to focus on the riddle, and the subject quickly changed to other forms of tomfoolery. A bit later in the conversation the Mad Hatter asks Alice if she has found the answer to the riddle, and she admits that she has not. She asks him for the answer, and he admits that he has no idea of the answer himself.

Alice sighed wearily. "I think you might do something better with the time," she said, "than wasting it in asking riddles that have no answers."

Of course, a riddle is designed to have an answer, it's supposed to have an answer, and many of Lewis Carroll's readers believed that even if Alice and the Mad Hatter had no clue what the answer was, surely Mr. Carroll himself would. He was so pestered by readers asking him for the answer that he finally responded in the preface to the 1896 edition of Alice. While he had not originally intended the Hatter's riddle to have an answer, he did admit to having one.

"Enquiries have been so often addressed to me, as to whether any answer to the Hatter's Riddle can be imagined, that I may as well put on record here what seems to me to be a fairly appropriate answer, viz: 'Because it can produce a few notes, tho they are very flat; and it is nevar put with the wrong end in front!' This, however, is merely an afterthought; the Riddle, as originally invented, had no answer at all."

So we finally had an answer. But as it had been admitted that it was only an answer, and not the answer, various wits have spent the following 100+ years in a quixotic search for The One True Answer. In this sort of venture there are no true losers, so I present for you the Raven and Writing Desk Hall of Fame:

Because neither can climb a tree. (Anonymous English children of yore, before 1896)

Because the notes for which they are noted are not noted for being musical notes. (Sam Loyd, 1914)

Because Poe wrote on both. (Sam Loyd, 1914)

Because there is a B in both and an N in neither. (Aldous Huxley, 1928)

Because it slopes with a flap. (Cyril Pearson, undated)

Because they both come with inky quills. (Anonymous)

Because you cannot ride either one of them like a bicycle. (Anonymous, 1930s)

Because they both stand on sticks. (Anonymous)

Because one is a rest for pens, the other is a pest for wrens. (Anonymous)

Because they both have bills. (Anonymous)

Because regardless of your efforts neither is likely to keep you well fed. (jessicaj, 2011)

Because both can be found in parliament. (Uberbanana, 2013)

The list can nevar be complete, and certainly not until you have made your contribution. Please let me know, why is a raven like a writing desk?

Many thanks to The Straight Dope and Martin Gardner's The Annotated Alice, which collected much of this information.

It may be pedantically observed that a raven is like a writing desk in many, many ways probably not intended to be addressed in the sort of extended identity logic applied to solving a riddle.

For example, clearly both are macroscopic physical objects. Both are manifested to us in more-or-less solid form, not liquid or gas, both are composed of of trillions of complex molecules and are decidedly lacking in material purity. Assuming the writing desk to be of wood (as most surely are), both are organic, and so the materials within both have known birth, life, and the inevitability of death. Of any particular raven and any particular writing desk, it may be posited with equal assurance of each that this particular one did not exist a few hundred years ago, and will no longer exist a few hundred years from now; the advance of human technology may ultimately extinguish both. Both have crunchy parts. Both will burn under the proper conditions, instead of melting or evaporating. Attempting sexual intercourse with either likely would yield unpleasant results, and if done in public, incarceration. In all the vastness of our Universe, both are found only in a narrow band of the outer crust of the third planet orbiting one particular small-to-medium-sized star in one particular small-to-medium-sized galaxy. (It may be that similar things do exist on other planets, but we would have to assume that some form of intelligent life has something comparable to our anatomy to be motivated to make something we would identify as a writing desk; and in the same vein, some very ravenlike creature may exist on another world, but at the DNA level, it would be no raven.)

Naturally, the original question itself relies upon pre-agreed conventions of meaning. For, the asker seeks not generic and universal truths of material objects; the unspoken question is, what characteristic is it that 'a writing desk' and 'a raven' have in common which sets them, as a duo, apart from other things? And, moreso, what words can be used in a manner that is especially descriptive of a characteristic of both, even if the word as applied to one has a completely different meaning for it's application to the other (both have 'legs'; the raven has a 'bill,' the writing table holds perhaps a pile of bills). But this leads us full circle to another generic point of familiarity, for both 'a raven' and 'a writing desk' are man-made symbolic representations, groups of letters strung together in the English language -- imagine how different the question would seem if it asked, 'Why is a cuervo like a bòrd-sgrìobhaidh,' though it would thusly be conveying the exact same ultimate meaning.

And so, here is my ultimate answer to the riddle: Why is a raven like a writing desk? Because the governing dynamics of our Universe are oriented toward producing planetary bodies covered with discrete macroscopic objects composed of collections of complex molecules; and because man chooses to define these concrete productions through ambiguous abstract symbols, that's why!!

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