I love those moments of reading serendipity when you’re in the middle of one book (Rubyfruit Jungle) in which one of the characters is reading another book you have on your table about to dive into. In Rubyfruit, Molly is reading Orlando and gets overcome, finally, by grief over Carl’s death, claiming to Carrie that she’s crying because she’s reading a really sad book. But Orlando is not sad– if anything it’s delightful to see Woolf’s pen frolic without care, running roughshod over the centuries that Orlando’s alive, galloping through Elizabethan times, then choking on exhaust from modern horseless carriages. VW wrote the book in 1928, flexing her muscles and winking at Vita Sackville-West, whom Orlando represents, raised as a boy then transforming to woman while serving as Ambassador to Turkey. It’s not only a tale of gender fluidity, but also offers a peek inside the head of a writer. Orlando is frustrated, wanting his poems to be admired by the great poets of the day, then realizes he’s only free to write when he does not desire fame. But first, he becomes a reader, “The disease gained rapidly upon him now in his solitude. He would read often six hours into the night… but worse was to come. For once the disease of reading has laid hold upon the system it weakens it so that it falls an easy prey to that other scourge which dwells in the ink pot and festers in the quill. The wretch takes to writing.”
She offers us an almost obscene look behind the curtain:

Anyone moderately familiar with the rigours of composition will not need to be told the story in detail; how he wrote and it seemed good; read and it seemed vile; corrected and tore up; cut out; put in; was in ecstasy; in despair; had his good nights and bad mornings; snatched at ideas and lost them; saw his book plain before him and it vanished; acted his people’s parts as he ate; mouthed them as he walked; now cried; now laughed; vacillated between this style and that; now preferred the heroic and pompous; next the plain and simple; now the vales of Tempe; then the fields of Kent or Cornwall; and could not decide whether he was the divinest genius or the greatest fool in the world.

Woolf is still thinking deeply about time:

The mind of man, moreover, works with equal strangeness upon the body of time. An hour, once it lodges in the queer element of the human spirit, may be stretched to fifty or a hundred times its clock length; on the other hand, an hour may be accurately represented on the timepiece of the mind by one second. This extraordinary discrepancy between time on the clock and time in the mind is less known than it should be and deserves fuller investigation.

Naturally any book about a man who becomes a woman who becomes a man must involve questions of dress. Once a woman, Orlando thinks “these skirts are plaguey things to have about one’s heels… Could I leap overboard and swim in clothes like these? No!” She finds that people treat her differently because of what she wears. Don a skirt and everyone is super-protective, flattering. Put on pants and roughhouse away with the boys. “There is much to support the view that it is clothes that wear us and not we them…”

So, having now worn skirts for a considerable time, a certain change was visible in Orlando, which is to be found even in her face. If we compare the picture of Orlando as a man with that or Orlando as a woman we shall see that though both are undoubtedly one and the same person, there are several changes. The man has his hand free to seize his sword; the woman must use hers to keep the satins from slipping from her shoulders. The man looks the world full in the face, as if it were made for his uses and fashioned to his liking. The woman takes a sidelong glance at it, full of subtlety, even of suspicion. Had they both worn the same clothes, it is possible that their outlook might have been the same too…. Clothes are but a symbol of something hid deep beneath.

Putting on men’s clothing again, Orlando ventures into the night and befriends streetwalkers, then reveals herself to be a woman. Nell brings Prue, Kitty, and Rose into the circle, and the five of them have a great time telling stories. VW’s biting cynicism is in grand form here:

So they would draw round the Punch bowl which Orlando made it her business to furnish generously, and many were the fine tales they told and many the amusing observations they made for it cannot be denied that when women get together–but hist–they are always careful to see that the doors are shut and that not a word of it gets into print. All they desire is–but hist again–is that not a man’s step on the stair? All they desire, we were about to say when the gentleman took the very words out of our mouths. Women have no desires, says this gentleman, coming into Nell’s parlour; only affectations. Without desires (she has served him and he is gone) their conversations cannot be of the slightest interest to anyone. “It is well known,” says Mr. S.W.,”that when they lack the stimulus of the other sex, women can find nothing to say to each other. When they are alone, they do not talk; they scratch.”

Time moves onward and yet Orlando does not age. She enters the 19th century and reluctantly takes on the fashion of the time, “dragged down by the weight of the crinoline which she had submissively adopted. It was heavier and more drab than any dress she had yet worn. None had ever so impeded her movements. No longer could she stride through the garden with her dogs, or run lightly to the high mound and fling herself beneath the oak tree. Her skirts collected damp leaves and straw.” These clothes engender a sort of dependency, and Orlando looks around for someone to lean on. She ends up marrying a man who was riding by on a horse, but who is soon off to his ship to round Cape Horn. In the first hours of their engagement, they talk endlessly, and VW has a nice discourse on conversation:

“Shel, my darling,” she began again, “tell me…” and so they talked two hours or more, perhaps about Cape Horn, perhaps not, and really it would profit little to write down what they said, for they knew each other so well that they could say anything they liked, which is tantamount to saying nothing, or saying such stupid, prosy things, as how to cook an omelette, or where to buy the best boots in London, which have no lustre taken from their setting, yet are positively of amazing beauty within it. For it has come about, by the wise economy of nature, that our modern spirit can almost dispense with language; the commonest expressions do, since no expressions do; hence the most ordinary conversation is often the most poetic, and the most poetic is precisely that which cannot be written down. For which reasons we leave a great blank here, which must be taken to indicate that the space is filled to repletion.